MiMeDB: Showing metabocard for Glycerophosphoinositol (MMDBc0000648)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:53 UTC

Update Date

2024-04-30 19:33:24 UTC

Metabolite ID

MMDBc0000648

Metabolite Identification

Common Name

Glycerophosphoinositol

Description

Glycerophosphoinositol (CAS: 16824-65-0), also known as 1-(sn-glycero-3-phospho)-1D-myo-inositol, is produced through deacylation by phospholipase B of the essential phospholipid phosphatidylinositol. Glycerophosphoinositols are ubiquitous phosphoinositide metabolites involved in the control of several cell functions. They exert their actions both intracellularly and by rapidly equilibrating across the plasma membrane. Their transport is mediated by the Glut2 transporter, the human ortholog of GIT1 (PMID: 17141226 ). Glycerophosphoinositol is a substrate for glycerophosphoinositol inositolphosphodiesterase (EC 3.1.4.43) and is involved in the following reaction: 1-(sn-glycero-3-phospho)-1D-myo-inositol + H2O = glycerol + 1D-myo-inositol 1-phosphate. It is also a substrate for glycerophosphoinositol glycerophosphodiesterase (EC 3.1.4.44) which catalyzes the chemical reaction: 1-(sn-glycero-3-phospho)-1D-myo-inositol + H2O = myo-inositol + sn-glycerol 3-phosphate.

Structure

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

HMDB0011649
     RDKit          3D
Glycerophosphoinositol
 40 40  0  0  0  0  0  0  0  0999 V2000
    1.4692    2.2449   -0.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460    0.8378   -0.3705 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.2551   -0.1185   -1.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0559    0.3777    0.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8711   -0.6968    0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886   -0.3670   -0.3615 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2790   -1.4266   -1.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979   -0.0853    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1663    0.9563    1.2688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5700    0.9412    0.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -0.2882    0.1896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3057   -0.1324    1.2187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8249   -1.4142    1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153    0.7549    0.7823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2120    2.1064    1.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901    0.6899   -0.6576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6396   -0.3906   -0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    0.5224   -1.5900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7898    1.6540   -1.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -0.7112   -1.0777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0848   -1.3226   -1.9987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.0118   -1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512   -0.9951    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876   -1.5996    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844    0.5576   -0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8837   -2.0558   -0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531   -1.0267    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361    0.1853   -0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082    1.7967    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -1.0824    0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9260    0.2297    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081   -1.9892    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3244    0.4562    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0140    2.5744    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3500    1.6091   -0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9285   -0.8292   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958    0.3464   -2.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    2.4029   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6711   -1.4561   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -2.2445   -1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 11  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  6
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  1
 12 31  1  1
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  6
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  1
 21 40  1  0
M  END


  Mrv1652311011917182D          

 21 21  0  0  1  0            999 V2000
   15.9251   -4.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6396   -3.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3542   -4.2524    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0688   -3.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3542   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2134   -4.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4973   -3.8426    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.7834   -4.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9105   -3.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0862   -3.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6392   -5.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0689   -4.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2134   -2.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6392   -1.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0689   -2.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6404   -4.2543    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.3550   -3.8419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.3550   -3.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.6404   -2.6044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.9259   -3.0169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.9259   -3.8419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  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
 21  6  1  6  0  0  0
 16 11  1  1  0  0  0
 17 12  1  6  0  0  0
 18 15  1  1  0  0  0
 19 14  1  6  0  0  0
 20 13  1  6  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000648

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@@H](O)COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H19O11P/c10-1-3(11)2-19-21(17,18)20-9-7(15)5(13)4(12)6(14)8(9)16/h3-16H,1-2H2,(H,17,18)/t3-,4-,5-,6+,7-,8-,9-/m1/s1

> <INCHI_KEY>
BMVUIWJCUQSHLZ-UJGXJMNGSA-N

> <FORMULA>
C9H19O11P

> <MOLECULAR_WEIGHT>
334.2143

> <EXACT_MASS>
334.066497962

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.803117703045235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2,3-dihydroxypropoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-2.49

> <JCHEM_LOGP>
-4.848051914666666

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.338351990720948

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8335431742771062

> <JCHEM_PKA_STRONGEST_BASIC>
-2.968964768452052

> <JCHEM_POLAR_SURFACE_AREA>
197.36999999999998

> <JCHEM_REFRACTIVITY>
63.385

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,3-dihydroxypropoxy([(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011649
     RDKit          3D
Glycerophosphoinositol
 40 40  0  0  0  0  0  0  0  0999 V2000
    1.4692    2.2449   -0.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460    0.8378   -0.3705 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.2551   -0.1185   -1.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0559    0.3777    0.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8711   -0.6968    0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886   -0.3670   -0.3615 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2790   -1.4266   -1.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979   -0.0853    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1663    0.9563    1.2688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5700    0.9412    0.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -0.2882    0.1896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3057   -0.1324    1.2187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8249   -1.4142    1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153    0.7549    0.7823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2120    2.1064    1.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901    0.6899   -0.6576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6396   -0.3906   -0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    0.5224   -1.5900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7898    1.6540   -1.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -0.7112   -1.0777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0848   -1.3226   -1.9987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.0118   -1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512   -0.9951    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876   -1.5996    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844    0.5576   -0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8837   -2.0558   -0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531   -1.0267    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361    0.1853   -0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082    1.7967    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -1.0824    0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9260    0.2297    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081   -1.9892    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3244    0.4562    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0140    2.5744    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3500    1.6091   -0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9285   -0.8292   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958    0.3464   -2.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    2.4029   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6711   -1.4561   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -2.2445   -1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 11  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  6
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  1
 12 31  1  1
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  6
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  1
 21 40  1  0
M  END

HEADER    PROTEIN                                 01-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-NOV-19         0                                  
HETATM    1  O   UNK     0      29.727  -7.938   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      31.061  -7.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.395  -7.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      33.728  -7.168   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      32.395  -9.478   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      37.732  -7.938   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      36.395  -7.173   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      35.062  -7.938   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      37.166  -5.839   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      35.628  -5.839   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      40.393  -9.480   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      43.062  -7.938   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      37.732  -4.861   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      40.393  -3.322   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      43.062  -4.861   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      40.395  -7.941   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.729  -7.171   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.729  -5.631   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.395  -4.862   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.062  -5.631   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.062  -7.171   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    8                                                       
CONECT    5    3                                                            
CONECT    6    7   21                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7    4                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11   16                                                            
CONECT   12   17                                                            
CONECT   13   20                                                            
CONECT   14   19                                                            
CONECT   15   18                                                            
CONECT   16   17   21   11                                                  
CONECT   17   16   18   12                                                  
CONECT   18   17   19   15                                                  
CONECT   19   18   20   14                                                  
CONECT   20   19   21   13                                                  
CONECT   21   16   20    6                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0011649
HETATM    1  O1  UNL     1       1.469   2.245  -0.772  1.00  0.00           O  
HETATM    2  P1  UNL     1       1.046   0.838  -0.371  1.00  0.00           P  
HETATM    3  O2  UNL     1       1.255  -0.118  -1.755  1.00  0.00           O  
HETATM    4  O3  UNL     1       2.056   0.378   0.887  1.00  0.00           O  
HETATM    5  C1  UNL     1       2.871  -0.697   0.589  1.00  0.00           C  
HETATM    6  C2  UNL     1       3.989  -0.367  -0.362  1.00  0.00           C  
HETATM    7  O4  UNL     1       4.279  -1.427  -1.236  1.00  0.00           O  
HETATM    8  C3  UNL     1       5.298  -0.085   0.368  1.00  0.00           C  
HETATM    9  O5  UNL     1       5.166   0.956   1.269  1.00  0.00           O  
HETATM   10  O6  UNL     1      -0.570   0.941   0.089  1.00  0.00           O  
HETATM   11  C4  UNL     1      -1.195  -0.288   0.190  1.00  0.00           C  
HETATM   12  C5  UNL     1      -2.306  -0.132   1.219  1.00  0.00           C  
HETATM   13  O7  UNL     1      -2.825  -1.414   1.457  1.00  0.00           O  
HETATM   14  C6  UNL     1      -3.415   0.755   0.782  1.00  0.00           C  
HETATM   15  O8  UNL     1      -3.212   2.106   1.104  1.00  0.00           O  
HETATM   16  C7  UNL     1      -3.790   0.690  -0.658  1.00  0.00           C  
HETATM   17  O9  UNL     1      -4.640  -0.391  -0.936  1.00  0.00           O  
HETATM   18  C8  UNL     1      -2.599   0.522  -1.590  1.00  0.00           C  
HETATM   19  O10 UNL     1      -1.790   1.654  -1.558  1.00  0.00           O  
HETATM   20  C9  UNL     1      -1.893  -0.711  -1.078  1.00  0.00           C  
HETATM   21  O11 UNL     1      -1.085  -1.323  -1.999  1.00  0.00           O  
HETATM   22  H1  UNL     1       1.593  -1.012  -1.545  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.351  -0.995   1.555  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.288  -1.600   0.278  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.784   0.558  -0.959  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.884  -2.056  -0.790  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.653  -1.027   0.820  1.00  0.00           H  
HETATM   28  H7  UNL     1       6.036   0.185  -0.426  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.308   1.797   0.746  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.515  -1.082   0.562  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.926   0.230   2.194  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.208  -1.989   1.958  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.324   0.456   1.365  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.014   2.574   0.733  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.350   1.609  -0.910  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.929  -0.829  -0.108  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.996   0.346  -2.605  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.172   2.403  -1.051  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.671  -1.456  -0.772  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.902  -2.245  -1.656  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4   10
CONECT    3   22
CONECT    4    5
CONECT    5    6   23   24
CONECT    6    7    8   25
CONECT    7   26
CONECT    8    9   27   28
CONECT    9   29
CONECT   10   11
CONECT   11   12   20   30
CONECT   12   13   14   31
CONECT   13   32
CONECT   14   15   16   33
CONECT   15   34
CONECT   16   17   18   35
CONECT   17   36
CONECT   18   19   20   37
CONECT   19   38
CONECT   20   21   39
CONECT   21   40
END

HMDB0011649
     RDKit          3D
Glycerophosphoinositol
 40 40  0  0  0  0  0  0  0  0999 V2000
    1.4692    2.2449   -0.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460    0.8378   -0.3705 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.2551   -0.1185   -1.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0559    0.3777    0.8867 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8711   -0.6968    0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9886   -0.3670   -0.3615 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2790   -1.4266   -1.2363 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979   -0.0853    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1663    0.9563    1.2688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5700    0.9412    0.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -0.2882    0.1896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3057   -0.1324    1.2187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8249   -1.4142    1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4153    0.7549    0.7823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2120    2.1064    1.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901    0.6899   -0.6576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6396   -0.3906   -0.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    0.5224   -1.5900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7898    1.6540   -1.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931   -0.7112   -1.0777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0848   -1.3226   -1.9987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.0118   -1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512   -0.9951    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876   -1.5996    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844    0.5576   -0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8837   -2.0558   -0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531   -1.0267    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361    0.1853   -0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082    1.7967    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -1.0824    0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9260    0.2297    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081   -1.9892    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3244    0.4562    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0140    2.5744    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3500    1.6091   -0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9285   -0.8292   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958    0.3464   -2.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    2.4029   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6711   -1.4561   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -2.2445   -1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 11  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  6
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  1
 12 31  1  1
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  6
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  1
 21 40  1  0
M  END

Synonyms

Value	Source
3-Phosphoglyceroinositol	ChEBI
Glyerophosphoinositol	ChEBI
GroPIns	ChEBI
sn-Glycero-3-phospho-1-inositol	ChEBI
1-(sn-Glycero-3-phospho)-1D-myo-inositol	Kegg
Glycerophosphoinositol	HMDB
alpha-Glycerophosphoryl inositol	HMDB
alpha-Glycerophosphorylinositol	HMDB
α-Glycerophosphoryl inositol	HMDB
α-Glycerophosphorylinositol	HMDB

Molecular Formula

C₉H₁₉O₁₁P

Average Mass

334.2143

Monoisotopic Mass

334.066497962

IUPAC Name

[(2R)-2,3-dihydroxypropoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

Traditional Name

(2R)-2,3-dihydroxypropoxy([(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

OC[C@@H](O)COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C9H19O11P/c10-1-3(11)2-19-21(17,18)20-9-7(15)5(13)4(12)6(14)8(9)16/h3-16H,1-2H2,(H,17,18)/t3-,4-,5-,6+,7-,8-,9-/m1/s1

InChI Key

BMVUIWJCUQSHLZ-UJGXJMNGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophosphoinositols. These are lipids containing a glycerol moiety carrying a phosphoinositol at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositols

Direct Parent

Glycerophosphoinositols

Alternative Parents

Substituents

Glycerophosphoinositol
Inositol phosphate
Cyclohexanol
Dialkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Cyclitol or derivatives
Cyclic alcohol
Secondary alcohol
Polyol
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

sn-glycerol 3-phosphates (CHEBI:18321 )
myo-inositol monophosphate derivative (CHEBI:18321 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	40.9 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-4.8	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	197.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.38 m³·mol⁻¹	ChemAxon
Polarizability	28.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0194171	Glycerophosphodiester phosphodiesterase 1	Unknown	Q9NZC3	Homo sapiens
MMDBp0196629	Glycerophosphoinositol inositolphosphodiesterase GDPD2	Enzyme	Q9HCC8	Homo sapiens

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	2	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0011649

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011624

KNApSAcK ID

Not Available

Chemspider ID

28184592

KEGG Compound ID

C01225

BioCyc ID

CPD-541

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18321

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Mariggio S, Iurisci C, Sebastia J, Patton-Vogt J, Corda D: Molecular characterization of a glycerophosphoinositol transporter in mammalian cells. FEBS Lett. 2006 Dec 22;580(30):6789-96. doi: 10.1016/j.febslet.2006.11.039. Epub 2006 Nov 27. [PubMed:17141226 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Glycerophosphoinositol (MMDBc0000648)

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Structure for #<Metabolite:0x00007f91fc31e210>

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