MiMeDB: Showing metabocard for 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate (MMDBc0029971)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:48:53 UTC

Update Date

2022-08-31 17:38:10 UTC

Metabolite ID

MMDBc0029971

Metabolite Identification

Common Name

2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate

Description

2-dehydro-3-deoxy-D-arabino-heptonate 7-phosphate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. DAHPS is involved in the biosynthesis of aromatic amino acids. Maritima DAHP synthase is a metalloenzyme. This report is the first description of a thermophilic eubacterial DAHP synthase. (PMID 12743122 ) DAHPS(Phe) is a metal-catalyzed oxidation system wherein bound substrate protects active-site residues from oxidative attack catalyzed by bound redox metal cofactor. (PMID 10049398 ) The first regulatory step in the synthesis of aromatic amino acids is catalyzed by 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (DAHPS). (PMID 15378531 ) While several similarities exist between the two enzymatic reactions, classic studies on the Escherichia coli enzymes have established that DAHPS is a metalloenzyme, whereas KDO8PS has no metal requirement. aeolicus KDO8PS is a metalloenzyme in vivo and point to a previously unrecognized relationship between the KDO8PS and DAHPS families. (PMID 10811802 )

Structure

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

HMDB0304124
     RDKit          3D
3-deoxy-D-arabino-heptulosonate-7-phosphate
 31 30  0  0  0  0  0  0  0  0999 V2000
   -5.1770   -0.5033    1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    0.5127    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829    1.7347    1.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4381    0.3939    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9732    1.4333   -0.3654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086   -0.9210   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -0.9020   -0.7517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6135   -0.3582   -2.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -0.2755    0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5564    1.0689    0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8903   -0.4635   -0.7350 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1231   -1.8024   -0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    0.0723    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869   -0.0818   -0.4289 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785    0.4794    0.4942 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.2036    0.3771    1.9715 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7473    2.0972    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721   -0.3811    0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9893    2.5488    0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -1.5900   -0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -1.3333    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -2.0113   -0.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   -1.0031   -2.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564   -0.8128    1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857    1.2894    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104    0.1349   -1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -1.9788   -1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    1.1676    0.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -0.4577    1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359    2.6001    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713   -1.0348   -0.6392 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  9 24  1  1
 10 25  1  0
 11 26  1  6
 12 27  1  0
 13 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv0541 02241222022D          

 18 17  0  0  1  0            999 V2000
    6.3519   -8.8641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0646   -9.2762    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6350   -9.2762    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3519   -8.0392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7849   -8.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0646  -10.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188   -8.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350  -10.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4976   -9.2762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3266   -9.2728    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.1549   -9.2728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3266   -8.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3266  -10.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036   -9.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933   -8.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788   -9.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1994  -10.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891   -8.0374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
  7 14  1  0  0  0  0
  1  2  1  0  0  0  0
 14 15  1  0  0  0  0
  1  3  1  0  0  0  0
 15 16  1  0  0  0  0
  1  4  1  6  0  0  0
 14 17  2  0  0  0  0
  2  5  1  0  0  0  0
 15 18  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029971

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/t3-,5-,6+/m1/s1

> <INCHI_KEY>
PJWIPEXIFFQAQZ-PUFIMZNGSA-N

> <FORMULA>
C7H13O10P

> <MOLECULAR_WEIGHT>
288.1459

> <EXACT_MASS>
288.024633148

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
22.367783841238907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonooxy)heptanoic acid

> <ALOGPS_LOGP>
-2.47

> <JCHEM_LOGP>
-2.5289322136666668

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.9174480444633493

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4688872906407804

> <JCHEM_PKA_STRONGEST_BASIC>
-3.271766798649698

> <JCHEM_POLAR_SURFACE_AREA>
181.82

> <JCHEM_REFRACTIVITY>
53.151700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DAHP

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304124
     RDKit          3D
3-deoxy-D-arabino-heptulosonate-7-phosphate
 31 30  0  0  0  0  0  0  0  0999 V2000
   -5.1770   -0.5033    1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    0.5127    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829    1.7347    1.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4381    0.3939    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9732    1.4333   -0.3654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086   -0.9210   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -0.9020   -0.7517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6135   -0.3582   -2.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -0.2755    0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5564    1.0689    0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8903   -0.4635   -0.7350 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1231   -1.8024   -0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    0.0723    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869   -0.0818   -0.4289 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785    0.4794    0.4942 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.2036    0.3771    1.9715 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7473    2.0972    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721   -0.3811    0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9893    2.5488    0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -1.5900   -0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -1.3333    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -2.0113   -0.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   -1.0031   -2.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564   -0.8128    1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857    1.2894    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104    0.1349   -1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -1.9788   -1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    1.1676    0.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -0.4577    1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359    2.6001    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713   -1.0348   -0.6392 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  9 24  1  1
 10 25  1  0
 11 26  1  6
 12 27  1  0
 13 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      11.857 -16.546   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.187 -17.316   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.519 -17.316   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.857 -15.007   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.532 -16.546   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.187 -18.855   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.182 -16.546   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.519 -18.855   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      15.862 -17.316   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0      17.410 -17.309   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0      18.956 -17.309   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      17.410 -15.763   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      17.410 -18.849   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.847 -17.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.521 -16.546   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.187 -17.314   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.839 -18.849   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.513 -15.003   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    6    1    5                                                  
CONECT    3    7    8    1                                                  
CONECT    4    1                                                            
CONECT    5    9    2                                                       
CONECT    6    2                                                            
CONECT    7    3   14                                                       
CONECT    8    3                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    7   15   17                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0304124
HETATM    1  O1  UNL     1      -5.177  -0.503   1.475  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.661   0.513   0.938  1.00  0.00           C  
HETATM    3  O2  UNL     1      -5.283   1.735   1.124  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.438   0.394   0.143  1.00  0.00           C  
HETATM    5  O3  UNL     1      -2.973   1.433  -0.365  1.00  0.00           O  
HETATM    6  C3  UNL     1      -2.809  -0.921  -0.026  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.494  -0.902  -0.752  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.614  -0.358  -2.007  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.418  -0.275   0.043  1.00  0.00           C  
HETATM   10  O5  UNL     1      -0.556   1.069   0.243  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.890  -0.463  -0.735  1.00  0.00           C  
HETATM   12  O6  UNL     1       1.123  -1.802  -0.989  1.00  0.00           O  
HETATM   13  C7  UNL     1       1.972   0.072   0.191  1.00  0.00           C  
HETATM   14  O7  UNL     1       3.187  -0.082  -0.429  1.00  0.00           O  
HETATM   15  P1  UNL     1       4.479   0.479   0.494  1.00  0.00           P  
HETATM   16  O8  UNL     1       4.204   0.377   1.971  1.00  0.00           O  
HETATM   17  O9  UNL     1       4.747   2.097   0.070  1.00  0.00           O  
HETATM   18  O10 UNL     1       5.872  -0.381   0.098  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.989   2.549   0.563  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.545  -1.590  -0.541  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.658  -1.333   1.010  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.215  -2.011  -0.853  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.838  -1.003  -2.713  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.256  -0.813   1.020  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.686   1.289   1.201  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.810   0.135  -1.651  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.048  -1.979  -1.243  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.778   1.168   0.289  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.893  -0.458   1.161  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.936   2.600   0.909  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.671  -1.035  -0.639  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   19
CONECT    4    5    5    6
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23
CONECT    9   10   11   24
CONECT   10   25
CONECT   11   12   13   26
CONECT   12   27
CONECT   13   14   28   29
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   30
CONECT   18   31
END

HMDB0304124
     RDKit          3D
3-deoxy-D-arabino-heptulosonate-7-phosphate
 31 30  0  0  0  0  0  0  0  0999 V2000
   -5.1770   -0.5033    1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    0.5127    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829    1.7347    1.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4381    0.3939    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9732    1.4333   -0.3654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086   -0.9210   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -0.9020   -0.7517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6135   -0.3582   -2.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -0.2755    0.0426 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5564    1.0689    0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8903   -0.4635   -0.7350 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1231   -1.8024   -0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9718    0.0723    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869   -0.0818   -0.4289 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785    0.4794    0.4942 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.2036    0.3771    1.9715 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7473    2.0972    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721   -0.3811    0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9893    2.5488    0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -1.5900   -0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -1.3333    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -2.0113   -0.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   -1.0031   -2.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2564   -0.8128    1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857    1.2894    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104    0.1349   -1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0482   -1.9788   -1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    1.1676    0.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -0.4577    1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9359    2.6001    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713   -1.0348   -0.6392 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  9 24  1  1
 10 25  1  0
 11 26  1  6
 12 27  1  0
 13 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
M  END

Synonyms

Value	Source
2-Dahp	ChEBI
2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate	ChEBI
3-Deoxy-arabino-heptulonate 7-phosphate	ChEBI
3-Deoxy-D-arabino-2-heptulosonic acid 7-(dihydrogen phosphate)	ChEBI
3-Deoxy-D-arabino-hept-2-ulosonate 7-phosphate	ChEBI
3-Deoxy-D-arabino-heptulosonate-7-phosphate	ChEBI
3-Deoxy-D-arabino-heptulosonic acid 7-phosphate	ChEBI
DAHP	ChEBI
2-Dehydro-3-deoxy-D-arabino-heptonic acid 7-phosphoric acid	Generator
3-Deoxy-arabino-heptulonic acid 7-phosphoric acid	Generator
3-Deoxy-D-arabino-2-heptulosonate 7-(dihydrogen phosphate)	Generator
3-Deoxy-D-arabino-2-heptulosonic acid 7-(dihydrogen phosphoric acid)	Generator
3-Deoxy-D-arabino-hept-2-ulosonic acid 7-phosphoric acid	Generator
3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid	Generator
3-Deoxy-D-arabino-heptulosonate 7-phosphate	Generator
3-Deoxy-D-arabino-heptulosonic acid 7-phosphoric acid	Generator
7-Phospho-2-dehydro-3-deoxy-D-arabino-heptonate	Generator
2-Dehydro-3-deoxy-D-arabino-heptulosonic acid-7-phosphate	MeSH
3-Deoxy-D-arabino-2-heptulosonic acid	MeSH
3-Deoxyarabinoheptulosonate-7-phosphate	MeSH
7-Phospho-2-keto-3-deoxy-D-arabinoheptonate	MeSH

Molecular Formula

C₇H₁₃O₁₀P

Average Mass

288.1459

Monoisotopic Mass

288.024633148

IUPAC Name

(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonooxy)heptanoic acid

Traditional Name

DAHP

CAS Registry Number

2627-73-8

SMILES

O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)CC(=O)C(O)=O

InChI Identifier

InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/t3-,5-,6+/m1/s1

InChI Key

PJWIPEXIFFQAQZ-PUFIMZNGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Heptose monosaccharide
Monosaccharide phosphate
Medium-chain keto acid
Monoalkyl phosphate
Sugar acid
Alpha-keto acid
Alkyl phosphate
Beta-hydroxy ketone
Phosphoric acid ester
Organic phosphoric acid derivative
Keto acid
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Polyol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketoaldonic acid phosphate (CHEBI:18150 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	14.1 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	53.15 m³·mol⁻¹	ChemAxon
Polarizability	22.37 Å³	ChemAxon
Number of Rings	0	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

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

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	Proteobacteria	8	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	300	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	166	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	12	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	107	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	115	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Bacteria	Firmicutes	23	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Cattle	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

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 Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0304124

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160647

PDB ID

Not Available

ChEBI ID

18150

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate (MMDBc0029971)

MOL for #<Metabolite:0x00007f9202862810>

3D MOL for #<Metabolite:0x00007f9202862810>

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3D PDB for #<Metabolite:0x00007f9202862810>

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Structure for #<Metabolite:0x00007f9202862810>

3D Structure for #<Metabolite:0x00007f9202862810>