MiMeDB: Showing metabocard for Vitamin A (MMDBc0000097)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:30:15 UTC

Update Date

2024-09-27 18:42:29 UTC

Metabolite ID

MMDBc0000097

Metabolite Identification

Common Name

Vitamin A

Description

Vitamin A (retinol) is a yellow fat-soluble, antioxidant vitamin important in vision and bone growth. It belongs to the family of chemical compounds known as retinoids. Retinol is ingested in a precursor form; animal sources (milk and eggs) contain retinyl esters, whereas plants (carrots, spinach) contain pro-vitamin A carotenoids. Hydrolysis of retinyl esters results in retinol while pro-vitamin A carotenoids can be cleaved to produce retinal. Retinal, also known as retinaldehyde, can be reversibly reduced to produce retinol or it can be irreversibly oxidized to produce retinoic acid. Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000305
     RDKit          3D
Vitamin A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.5592   -2.4974   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0570   -1.3113   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4485   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -0.7661   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -0.0504   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.4566   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -1.6940   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175    0.3254    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    0.0090   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    0.8100    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4142    0.6094    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9883   -0.5182   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060    1.5209    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689    1.4803    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1510    0.4010   -0.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    0.7400    0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    0.5617    2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.0075   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0162    0.8503    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    0.3804   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5365   -1.1460   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -3.2035   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -3.0174   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618   -2.1692   -2.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -1.6644   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.8444    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -1.6473   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -2.4991   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012   -2.0813   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    1.2108    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.8552   -0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223    1.6783    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.1610   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265   -0.2428   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5732   -1.1840    0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    2.3796    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1084    1.5121    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0054    2.3894   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0346    0.1503    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    0.3620    2.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4618    2.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342   -0.3357    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400    2.5887   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396    2.6450    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.7458   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3657    0.2390    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9195    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8385    0.5286   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455    0.7999   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9261   -1.6428    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110   -1.5587   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
M  END


  Mrv1652303192021392D          

 21 21  0  0  0  0            999 V2000
10000.386410003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.101110002.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.815610003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.530110002.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.244410003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.959910002.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.673010003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.388410002.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.105810003.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.819010002.7076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.673010003.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.815610003.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.954610001.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.484710002.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.959410003.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.958010003.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.243410002.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.243410001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.958010001.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.672710001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.672710002.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000097

> <DATABASE_NAME>
MIME

> <SMILES>
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

> <INCHI_KEY>
FPIPGXGPPPQFEQ-OVSJKPMPSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.4516

> <EXACT_MASS>
286.229665582

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.5403584594368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol

> <ALOGPS_LOGP>
6.38

> <JCHEM_LOGP>
4.694093173000001

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.435769749539965

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1707943115512176

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
97.92339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-sol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000305
     RDKit          3D
Vitamin A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.5592   -2.4974   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0570   -1.3113   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4485   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -0.7661   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -0.0504   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.4566   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -1.6940   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175    0.3254    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    0.0090   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    0.8100    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4142    0.6094    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9883   -0.5182   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060    1.5209    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689    1.4803    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1510    0.4010   -0.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    0.7400    0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    0.5617    2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.0075   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0162    0.8503    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    0.3804   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5365   -1.1460   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -3.2035   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -3.0174   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618   -2.1692   -2.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -1.6644   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.8444    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -1.6473   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -2.4991   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012   -2.0813   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    1.2108    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.8552   -0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223    1.6783    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.1610   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265   -0.2428   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5732   -1.1840    0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    2.3796    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1084    1.5121    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0054    2.3894   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0346    0.1503    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    0.3620    2.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4618    2.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342   -0.3357    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400    2.5887   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396    2.6450    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.7458   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3657    0.2390    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9195    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8385    0.5286   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455    0.7999   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9261   -1.6428    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110   -1.5587   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8667.3888672.491   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.7228671.721   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.0568672.491   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.3908671.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8672.7238672.491   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.0588671.721   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8675.3908672.491   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8676.7258671.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8678.0648672.491   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8679.3958671.721   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8675.3908674.030   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.0568674.030   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.5828668.734   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.5718670.450   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.7248674.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.7228672.491   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.3888671.721   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3888670.181   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.7228669.411   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.0568670.181   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.0568671.721   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    3                                                            
CONECT   13   20                                                            
CONECT   14   20                                                            
CONECT   15   16                                                            
CONECT   16   17   21   15                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   13   14                                             
CONECT   21   16   20    1                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0000305
HETATM    1  C1  UNL     1      -3.559  -2.497  -1.423  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.057  -1.311  -0.645  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.172  -0.448  -0.138  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.745  -0.766  -0.411  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.732  -0.050  -0.013  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.667  -0.457  -0.338  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.893  -1.694  -1.111  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.618   0.325   0.100  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.038   0.009  -0.172  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.990   0.810   0.279  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.414   0.609   0.080  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.988  -0.518  -0.657  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.206   1.521   0.609  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.669   1.480   0.508  1.00  0.00           C  
HETATM   15  O1  UNL     1       8.151   0.401  -0.193  1.00  0.00           O  
HETATM   16  C15 UNL     1      -3.539   0.740   0.654  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.869   0.562   2.016  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.035   2.007  -0.026  1.00  0.00           C  
HETATM   19  C18 UNL     1      -5.016   0.850   0.813  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.732   0.380  -0.399  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.537  -1.146  -0.492  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.016  -3.204  -0.789  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.442  -3.017  -1.836  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.962  -2.169  -2.298  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.480  -1.664  -0.994  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.909   0.844   0.550  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.451  -1.647  -2.129  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.287  -2.499  -0.585  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.901  -2.081  -1.125  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.369   1.211   0.665  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.321  -0.855  -0.731  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.622   1.678   0.842  1.00  0.00           H  
HETATM   33  H12 UNL     1       5.140  -1.161  -1.039  1.00  0.00           H  
HETATM   34  H13 UNL     1       6.527  -0.243  -1.591  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.573  -1.184   0.017  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.754   2.380   1.170  1.00  0.00           H  
HETATM   37  H16 UNL     1       8.108   1.512   1.539  1.00  0.00           H  
HETATM   38  H17 UNL     1       8.005   2.389  -0.072  1.00  0.00           H  
HETATM   39  H18 UNL     1       9.035   0.150   0.209  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.701   0.362   2.764  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.316   1.462   2.319  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.234  -0.336   2.075  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.940   2.589  -0.360  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.440   2.645   0.649  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.487   1.746  -0.955  1.00  0.00           H  
HETATM   46  H25 UNL     1      -5.366   0.239   1.681  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.321   1.919   0.984  1.00  0.00           H  
HETATM   48  H27 UNL     1      -6.839   0.529  -0.293  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.346   0.800  -1.332  1.00  0.00           H  
HETATM   50  H29 UNL     1      -5.926  -1.643   0.404  1.00  0.00           H  
HETATM   51  H30 UNL     1      -6.011  -1.559  -1.388  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   21
CONECT    3    4   16
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7    8    8
CONECT    7   27   28   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   13   13
CONECT   12   33   34   35
CONECT   13   14   36
CONECT   14   15   37   38
CONECT   15   39
CONECT   16   17   18   19
CONECT   17   40   41   42
CONECT   18   43   44   45
CONECT   19   20   46   47
CONECT   20   21   48   49
CONECT   21   50   51
END

HMDB0000305
     RDKit          3D
Vitamin A
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.5592   -2.4974   -1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0570   -1.3113   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4485   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -0.7661   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7322   -0.0504   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -0.4566   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -1.6940   -1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175    0.3254    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    0.0090   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904    0.8100    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4142    0.6094    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9883   -0.5182   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060    1.5209    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689    1.4803    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1510    0.4010   -0.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5390    0.7400    0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    0.5617    2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    2.0075   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0162    0.8503    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7324    0.3804   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5365   -1.1460   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -3.2035   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -3.0174   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618   -2.1692   -2.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -1.6644   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.8444    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -1.6473   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -2.4991   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012   -2.0813   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    1.2108    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.8552   -0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223    1.6783    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -1.1610   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265   -0.2428   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5732   -1.1840    0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7539    2.3796    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1084    1.5121    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0054    2.3894   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0346    0.1503    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7007    0.3620    2.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4618    2.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342   -0.3357    2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400    2.5887   -0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396    2.6450    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4871    1.7458   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3657    0.2390    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9195    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8385    0.5286   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455    0.7999   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9261   -1.6428    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110   -1.5587   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
M  END

Synonyms

Value	Source
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol	ChEBI
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol	ChEBI
all-trans Retinol	ChEBI
all-trans-Retinyl alcohol	ChEBI
all-trans-Vitamin a	ChEBI
all-trans-Vitamin a alcohol	ChEBI
Alphalin	ChEBI
Aquasol a	ChEBI
Chocola a	ChEBI
Retinol	ChEBI
Retinol (vit a)	ChEBI
Retinolum	ChEBI
trans-Retinol	ChEBI
Vitamin a alcohol	ChEBI
Vitamin a1	ChEBI
Vitamin a1 alcohol	ChEBI
11-cis-Retinol	MeSH
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomer	MeSH
all trans Retinol	MeSH
all-trans-Retinol	MeSH
b-Retinol	HMDB
beta-Retinol	HMDB
Vitamin a	ChEBI

Molecular Formula

C₂₀H₃₀O

Average Mass

286.4516

Monoisotopic Mass

286.229665582

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol

Traditional Name

α-sol

CAS Registry Number

68-26-8

SMILES

C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI Key

FPIPGXGPPPQFEQ-OVSJKPMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoid skeleton
Diterpenoid
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinol (CHEBI:17336 )
Retinoids (C00473 )
Fat-soluble vitamins (C00473 )
Retinoids (LMPR01090000 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0076 g/L	ALOGPS
logP	6.38	ALOGPS
logP	4.69	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	16.44	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.92 m³·mol⁻¹	ChemAxon
Polarizability	36.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Epidermis
Feces
Fibroblasts
Intestine
Kidney
Liver
Neuron
Placenta
Saliva
Spleen
Testis

Tissue Locations

Adipose Tissue
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Placenta
Spleen
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191913	Diacylglycerol O-acyltransferase 1	Enzyme	O75907	Homo sapiens
MMDBp0192152	11-cis retinol dehydrogenase	Unknown	Q92781	Homo sapiens
MMDBp0192165	Alcohol dehydrogenase 4	Unknown	P08319	Homo sapiens
MMDBp0192400	Alcohol dehydrogenase class-3	Unknown	P11766	Homo sapiens
MMDBp0192402	Alcohol dehydrogenase 1B	Unknown	P00325	Homo sapiens
MMDBp0192403	Alcohol dehydrogenase class 4 mu/sigma chain	Unknown	P40394	Homo sapiens
MMDBp0192404	Alcohol dehydrogenase 1A	Unknown	P07327	Homo sapiens
MMDBp0192405	Alcohol dehydrogenase 6	Unknown	P28332	Homo sapiens
MMDBp0192406	Alcohol dehydrogenase 1C	Unknown	P00326	Homo sapiens
MMDBp0193325	Lecithin retinol acyltransferase	Enzyme	O95237	Homo sapiens
MMDBp0193705	17-beta-hydroxysteroid dehydrogenase type 6	Unknown	O14756	Homo sapiens
MMDBp0193979	Diacylglycerol O-acyltransferase 2	Enzyme	Q96PD7	Homo sapiens
MMDBp0194003	Retinol dehydrogenase 8	Enzyme	Q9NYR8	Homo sapiens
MMDBp0194004	Retinol dehydrogenase 11	Enzyme	Q8TC12	Homo sapiens
MMDBp0194028	Retinol dehydrogenase 10	Enzyme	Q8IZV5	Homo sapiens
MMDBp0194074	Acyl-CoA wax alcohol acyltransferase 1	Enzyme	Q58HT5	Homo sapiens
MMDBp0194075	Acyl-CoA wax alcohol acyltransferase 2	Enzyme	Q6E213	Homo sapiens
MMDBp0195061	All-trans-retinol 13,14-reductase	Unknown	Q6NUM9	Homo sapiens
MMDBp0195653	Short-chain dehydrogenase/reductase 3	Enzyme	O75911	Homo sapiens
MMDBp0196941	Epidermal retinol dehydrogenase 2	Unknown	Q8N3Y7

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Abetalipoproteinemia	Decreased	Association	Human Blood	HMDB	2944375
Endometrial cancer		Association	Human Blood	HMDB	19235557

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota	Apicomplexa	1		Microbial culture
Bacteria/Eubacteria	Firmicutes	198	Human ; Human feces; Pig ; Cattle ; Human stool; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	113	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria	Actinobacteria	11	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	67	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	28	Human feces; Human ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	3	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	13	Human ; Human feces; Pig ; Cattle ; Human stool; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	5	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
General Exposome	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.45				uM	Adult (>18 years old)	Male	Abetalipoproteinemia	HMDB	2944375
Human Blood	Detected and Quantified	2.0		1.2	2.5	uM	Adult (>18 years old)	Female	Endometrial cancer	HMDB	19235557
Human Blood	Detected and Quantified	2.50	0.86			uM	Adult (>18 years old)	Both	Hemodialysis	HMDB	16221095
Human Blood	Detected and Quantified	1.466	0.349			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	16925883
Human Blood	Detected and Quantified	1.42				uM	Adult (>18 years old)	Female	Normal	HMDB	9109609
Human Blood	Detected and Quantified	1.63				uM	Adult (>18 years old)	Female	Normal	HMDB	9109609
Human Blood	Detected and Quantified	1.99				uM	Adult (>18 years old)	Male	Normal	HMDB	9109609
Human Blood	Detected and Quantified	1.993				uM	Adult (>18 years old)	Female	Normal	HMDB	20332276
Human Blood	Detected and Quantified	2.18				uM	Adult (>18 years old)	Male	Normal	HMDB	9109609
Human Blood	Detected and Quantified	2.18				uM	Adult (>18 years old)	Female	Normal	HMDB	19371448
Human Blood	Detected and Quantified	2.3				uM	Adult (>18 years old)	Both	Normal	HMDB	15735096
Human Blood	Detected and Quantified	2.47				uM	Adult (>18 years old)	Male	Normal	HMDB	19371448
Human Blood	Detected and Quantified			0.530	2.100	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	2944375
Human Blood	Detected and Quantified	0.580	0.360			uM	Adult (>18 years old)	Male	Normal	HMDB	1878353
Human Blood	Detected and Quantified	0.831	0.499			uM	Adult (>18 years old)	Male	Normal	HMDB	1878353
Human Blood	Detected and Quantified	1.02		0.34	2.1	uM	Adolescent (13-18 years old)	Both	Normal	HMDB	7657478
Human Blood	Detected and Quantified	1.445	0.384			uM	Adult (>18 years old)	Female	Normal	HMDB	10427874
Human Blood	Detected and Quantified	1.740	0.540			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.770	0.740			uM	Adult (>18 years old)	Female	Normal	HMDB	15051849
Human Blood	Detected and Quantified	1.790	0.530			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.790	0.540			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.800	0.500			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.810	0.550			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.820	0.510			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.820	0.560			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.840	0.530			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.850	0.530			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.860	0.450			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.870	0.510			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.880	0.430			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.880	0.470			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.880	0.480			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.890	0.420			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.910	0.430			uM	Adult (>18 years old)	Female	Normal	HMDB	1512628
Human Blood	Detected and Quantified	1.950	0.470			uM	Adult (>18 years old)	Both	Normal	HMDB	17378949
Human Blood	Detected and Quantified	1.950	0.610			uM	Adult (>18 years old)	Female	Normal	HMDB	8424386
Human Blood	Detected and Quantified	1.951	0.520			uM	Adult (>18 years old)	Both	Normal	HMDB	6624705
Human Blood	Detected and Quantified	1.970	0.650			uM	Adult (>18 years old)	Female	Normal	HMDB	8424386
Human Blood	Detected and Quantified	1.980	0.540			uM	Adult (>18 years old)	Male	Normal	HMDB	8424386
Human Blood	Detected and Quantified	2.0600	0.620			uM	Adult (>18 years old)	Both	Normal	HMDB	15051849
Human Blood	Detected and Quantified	2.0736	0.485			uM	Adult (>18 years old)	Male	Normal	HMDB	1878353
Human Blood	Detected and Quantified	2.0800	0.620			uM	Adult (>18 years old)	Male	Normal	HMDB	8424386
Human Blood	Detected and Quantified	2.0841	0.499			uM	Adult (>18 years old)	Male	Normal	HMDB	1878353
Human Blood	Detected and Quantified	2.130	0.380			uM	Adult (>18 years old)	Male	Normal	HMDB	1512628
Human Blood	Detected and Quantified	2.182	0.499			uM	Adult (>18 years old)	Male	Normal	HMDB	1878353
Human Blood	Detected and Quantified	2.200	0.634			uM	Adult (>18 years old)	Both	Normal	HMDB	16755268
Human Blood	Detected and Quantified	2.220	0.496			uM	Adult (>18 years old)	Male	Normal	HMDB	1878353
Human Blood	Detected and Quantified	2.220	0.590			uM	Adult (>18 years old)	Both	Normal	HMDB	15051849
Human Blood	Detected and Quantified	2.3		1.2	3.5	uM	Adult (>18 years old)	Female	Normal	HMDB	19235557
Human Blood	Detected and Quantified	2.310	0.960			uM	Adult (>18 years old)	Male	Normal	HMDB	15051849
Human Blood	Detected and Quantified	2.390	0.800			uM	Adult (>18 years old)	Female	Normal	HMDB	15051849
Human Blood	Detected and Quantified	2.391	0.782			uM	Adult (>18 years old)	Female	Normal	HMDB	18813024
Human Blood	Detected and Quantified	2.400	0.900			uM	Adult (>18 years old)	Male	Normal	HMDB	8424386
Human Blood	Detected and Quantified	2.470	0.770			uM	Adult (>18 years old)	Male	Normal	HMDB	15051849
Human Blood	Detected and Quantified	2.580	0.710			uM	Adult (>18 years old)	Both	Normal	HMDB	15051849
Human Blood	Detected and Quantified	2.700	1.100			uM	Adult (>18 years old)	Female	Normal	HMDB	8424386
Human Blood	Detected and Quantified	2.720	0.790			uM	Adult (>18 years old)	Both	Normal	HMDB	15051849
Human Blood	Detected and Quantified	5.666	2.0387			uM	Adult (>18 years old)	Male	Normal	HMDB	11454500
Human Blood	Detected and Quantified	5.732	2.217			uM	Adult (>18 years old)	Both	Normal	HMDB	11454500
Human Blood	Detected and Quantified	5.781	2.356			uM	Adult (>18 years old)	Female	Normal	HMDB	11454500
Human Blood	Detected and Quantified	5.861	2.726			uM	Adult (>18 years old)	Female	Normal	HMDB	11454500
Human Blood	Detected and Quantified	6.113	2.594			uM	Adult (>18 years old)	Both	Normal	HMDB	11454500
Human Blood	Detected and Quantified	6.249	1.850			uM	Adult (>18 years old)	Both	Normal	HMDB	6624705
Human Blood	Detected and Quantified	6.553	2.315			uM	Adult (>18 years old)	Male	Normal	HMDB	11454500
Human Blood	Detected and Quantified			1	2	uM	Children (1-13 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			1	2	uM	Adolescent (13-18 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			1	2	uM	Adult (>18 years old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified			0	2	uM	Infant (0-1 year old)	Both	Normal	HMDB	CALIPER Paediatric Reference Intervals
Human Blood	Detected and Quantified	0.78	0.33			uM	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	1.76	0.44			uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	1.84	0.46			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.015	0.010			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620

External Links

HMDB ID

HMDB0000305

DrugBank ID

DB00162

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023841

KNApSAcK ID

C00031437

Chemspider ID

Not Available

KEGG Compound ID

C17276

BioCyc ID

CPD-13524

BiGG ID

Not Available

Wikipedia Link

Vitamin_A

METLIN ID

Not Available

PubChem Compound

445354

PDB ID

Not Available

ChEBI ID

17336

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Norum KR, Blomhoff R: McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage. Am J Clin Nutr. 1992 Oct;56(4):735-44. doi: 10.1093/ajcn/56.4.735. [PubMed:1414975 ]
Graham-Maar RC, Schall JI, Stettler N, Zemel BS, Stallings VA: Elevated vitamin A intake and serum retinol in preadolescent children with cystic fibrosis. Am J Clin Nutr. 2006 Jul;84(1):174-82. doi: 10.1093/ajcn/84.1.174. [PubMed:16825693 ]
Sorenson AW, Delhumeau C, Bernstein MS, Costanza MC, Morabia A: Impact of 'Mad Cow Disease' publicity on trends in meat and total vitamin A consumption in Geneva between 1993 and 2000. Eur J Clin Nutr. 2003 Jan;57(1):177-85. doi: 10.1038/sj.ejcn.1601576. [PubMed:12548314 ]
Alberts D, Ranger-Moore J, Einspahr J, Saboda K, Bozzo P, Liu Y, Xu XC, Lotan R, Warneke J, Salasche S, Stratton S, Levine N, Goldman R, Islas M, Duckett L, Thompson D, Bartels P, Foote J: Safety and efficacy of dose-intensive oral vitamin A in subjects with sun-damaged skin. Clin Cancer Res. 2004 Mar 15;10(6):1875-80. doi: 10.1158/1078-0432.ccr-03-0188. [PubMed:15041701 ]
Wieringa FT, Dijkhuizen MA, West CE, Thurnham DI, Muhilal, Van der Meer JW: Redistribution of vitamin A after iron supplementation in Indonesian infants. Am J Clin Nutr. 2003 Mar;77(3):651-7. doi: 10.1093/ajcn/77.3.651. [PubMed:12600856 ]
Egeland GM, Berti P, Soueida R, Arbour LT, Receveur O, Kuhnlein HV: Age differences in vitamin A intake among Canadian Inuit. Can J Public Health. 2004 Nov-Dec;95(6):465-9. [PubMed:15622799 ]
Ribaya-Mercado JD, Solon FS, Fermin LS, Perfecto CS, Solon JA, Dolnikowski GG, Russell RM: Dietary vitamin A intakes of Filipino elders with adequate or low liver vitamin A concentrations as assessed by the deuterated-retinol-dilution method: implications for dietary requirements. Am J Clin Nutr. 2004 Apr;79(4):633-41. doi: 10.1093/ajcn/79.4.633. [PubMed:15051608 ]
Kieu NT, Yurie K, Hung NT, Yamamoto S, Chuyen NV: Simultaneous analysis of retinol, beta-carotene and tocopherol levels in serum of Vietnamese populations with different incomes. Asia Pac J Clin Nutr. 2002;11(2):92-7. doi: 10.1046/j.1440-6047.2002.00283.x. [PubMed:12074187 ]
Torma H, Vahlquist A: Vitamin A esterification in human epidermis: a relation to keratinocyte differentiation. J Invest Dermatol. 1990 Jan;94(1):132-8. doi: 10.1111/1523-1747.ep12873990. [PubMed:2295828 ]
Allen LH, Haskell M: Estimating the potential for vitamin A toxicity in women and young children. J Nutr. 2002 Sep;132(9 Suppl):2907S-2919S. doi: 10.1093/jn/132.9.2907S. [PubMed:12221269 ]
Ribaya-Mercado JD, Solomons NW, Medrano Y, Bulux J, Dolnikowski GG, Russell RM, Wallace CB: Use of the deuterated-retinol-dilution technique to monitor the vitamin A status of Nicaraguan schoolchildren 1 y after initiation of the Nicaraguan national program of sugar fortification with vitamin A. Am J Clin Nutr. 2004 Nov;80(5):1291-8. doi: 10.1093/ajcn/80.5.1291. [PubMed:15531678 ]
Marquez M, Yepez CE, Sutil-Naranjo R, Rincon M: [Basic aspects and measurement of the antioxidant vitamins A and E]. Invest Clin. 2002 Sep;43(3):191-204. [PubMed:12229281 ]
Mills JP, Penniston KL, Tanumihardjo SA: Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A. Int J Vitam Nutr Res. 2005 Mar;75(2):126-32. doi: 10.1024/0300-9831.75.2.126. [PubMed:15929633 ]
Penniston KL, Tanumihardjo SA: The acute and chronic toxic effects of vitamin A. Am J Clin Nutr. 2006 Feb;83(2):191-201. doi: 10.1093/ajcn/83.2.191. [PubMed:16469975 ]
Jumpsen JA, Brown NE, Thomson AB, Paul Man SF, Goh YK, Ma D, Clandinin MT: Fatty acids in blood and intestine following docosahexaenoic acid supplementation in adults with cystic fibrosis. J Cyst Fibros. 2006 May;5(2):77-84. doi: 10.1016/j.jcf.2006.01.004. Epub 2006 Feb 28. [PubMed:16507353 ]

Showing metabocard for Vitamin A (MMDBc0000097)

MOL for #<Metabolite:0x00007f9252a45df8>

3D MOL for #<Metabolite:0x00007f9252a45df8>

3D SDF for #<Metabolite:0x00007f9252a45df8>

3D-SDF for #<Metabolite:0x00007f9252a45df8>

PDB for #<Metabolite:0x00007f9252a45df8>

3D PDB for #<Metabolite:0x00007f9252a45df8>

SMILES for #<Metabolite:0x00007f9252a45df8>

INCHI for #<Metabolite:0x00007f9252a45df8>

Structure for #<Metabolite:0x00007f9252a45df8>

3D Structure for #<Metabolite:0x00007f9252a45df8>