Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:27:33 UTC

Update Date

2021-09-26 22:51:56 UTC

HMDB ID

HMDB0244292

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Keto-3-deoxy-D-manno-octulosonic acid

Description

Keto-3-deoxy-D-manno-octulosonic acid, also known as 3-deoxy-D-mannoctulosonate or 2-keto-3-deoxyoctonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Based on a literature review very few articles have been published on Keto-3-deoxy-D-manno-octulosonic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Keto-3-deoxy-d-manno-octulosonic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Keto-3-deoxy-D-manno-octulosonic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0244292
     RDKit          3D
Keto-3-deoxy-D-manno-octulosonic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.1849    2.1090   -0.9000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    1.0589   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2444    1.2175   -0.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864   -0.2414   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1066   -1.2271   -0.4611 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8777   -0.5919   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9585    0.5694   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735    1.4300    0.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5173    0.1886   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446   -0.6875   -1.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.3559    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594   -1.5482    0.9342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5445   -0.5862    0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9332   -1.5924   -0.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3747    0.6251    0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727    1.7104    1.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7269    1.1093    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -1.3975   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -1.0919    0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2279    1.1910   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010    0.9796    1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    1.1295   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4798   -1.6346   -1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8518    0.3466    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036   -2.0956    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300   -0.9223    1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9665   -2.4598    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618    0.9048   -0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4316    0.3566    0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4689    1.5060    1.9932 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
 13 15  1  0
 15 16  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1533005021511352D          

 16 15  0  0  0  0            999 V2000
    2.2836    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  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  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244292

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC(O)C(O)C(O)C(O)CC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)

> <INCHI_KEY>
KYQCXUMVJGMDNG-UHFFFAOYSA-N

> <FORMULA>
C8H14O8

> <MOLECULAR_WEIGHT>
238.192

> <EXACT_MASS>
238.068867411

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.760815198892317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,6,7,8-pentahydroxy-2-oxooctanoic acid

> <ALOGPS_LOGP>
-2.54

> <JCHEM_LOGP>
-3.0357011243333334

> <ALOGPS_LOGS>
-0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.630062785724625

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9038228877924785

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742108660118767

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
48.241299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,6,7,8-pentahydroxy-2-oxooctanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244292
     RDKit          3D
Keto-3-deoxy-D-manno-octulosonic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.1849    2.1090   -0.9000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    1.0589   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2444    1.2175   -0.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864   -0.2414   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1066   -1.2271   -0.4611 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8777   -0.5919   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9585    0.5694   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735    1.4300    0.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5173    0.1886   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446   -0.6875   -1.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.3559    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594   -1.5482    0.9342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5445   -0.5862    0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9332   -1.5924   -0.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3747    0.6251    0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727    1.7104    1.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7269    1.1093    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -1.3975   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -1.0919    0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2279    1.1910   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010    0.9796    1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    1.1295   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4798   -1.6346   -1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8518    0.3466    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036   -2.0956    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300   -0.9223    1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9665   -2.4598    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618    0.9048   -0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4316    0.3566    0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4689    1.5060    1.9932 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
 13 15  1  0
 15 16  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 02-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-MAY-15         0                                  
HETATM    1  O   UNK     0       4.263   4.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.264   6.311   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.597   2.461   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.598   6.311   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0244292
HETATM    1  O1  UNL     1       3.185   2.109  -0.900  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.830   1.059  -0.762  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.244   1.217  -0.794  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.286  -0.241  -0.582  1.00  0.00           C  
HETATM    5  O3  UNL     1       4.107  -1.227  -0.461  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.878  -0.592  -0.517  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.959   0.569  -0.567  1.00  0.00           C  
HETATM    8  O4  UNL     1       1.173   1.430   0.501  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.517   0.189  -0.675  1.00  0.00           C  
HETATM   10  O5  UNL     1      -0.645  -0.687  -1.750  1.00  0.00           O  
HETATM   11  C6  UNL     1      -1.071  -0.356   0.571  1.00  0.00           C  
HETATM   12  O6  UNL     1      -0.459  -1.548   0.934  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.545  -0.586   0.598  1.00  0.00           C  
HETATM   14  O7  UNL     1      -2.933  -1.592  -0.282  1.00  0.00           O  
HETATM   15  C8  UNL     1      -3.375   0.625   0.291  1.00  0.00           C  
HETATM   16  O8  UNL     1      -3.073   1.710   1.116  1.00  0.00           O  
HETATM   17  H1  UNL     1       5.727   1.109   0.100  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.592  -1.398  -1.245  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.715  -1.092   0.494  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.228   1.191  -1.487  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.101   0.980   1.383  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.013   1.129  -1.025  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.480  -1.635  -1.466  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.852   0.347   1.430  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.004  -2.096   1.545  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.830  -0.922   1.616  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.966  -2.460   0.196  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.362   0.905  -0.779  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.432   0.357   0.523  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.469   1.506   1.993  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5    6
CONECT    6    7   18   19
CONECT    7    8    9   20
CONECT    8   21
CONECT    9   10   11   22
CONECT   10   23
CONECT   11   12   13   24
CONECT   12   25
CONECT   13   14   15   26
CONECT   14   27
CONECT   15   16   28   29
CONECT   16   30
END

HMDB0244292
     RDKit          3D
Keto-3-deoxy-D-manno-octulosonic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
    3.1849    2.1090   -0.9000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    1.0589   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2444    1.2175   -0.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864   -0.2414   -0.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1066   -1.2271   -0.4611 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8777   -0.5919   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9585    0.5694   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1735    1.4300    0.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5173    0.1886   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446   -0.6875   -1.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.3559    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594   -1.5482    0.9342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5445   -0.5862    0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9332   -1.5924   -0.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3747    0.6251    0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727    1.7104    1.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7269    1.1093    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -1.3975   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -1.0919    0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2279    1.1910   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010    0.9796    1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    1.1295   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4798   -1.6346   -1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8518    0.3466    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036   -2.0956    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300   -0.9223    1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9665   -2.4598    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618    0.9048   -0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4316    0.3566    0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4689    1.5060    1.9932 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
 13 15  1  0
 15 16  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Keto-3-deoxy-D-manno-octulosonate	Generator
3-Deoxyoctulosonate	HMDB
(D-Manno)-isomer OF 2-keto-3-deoxyoctonate	HMDB
2-Keto-3-deoxy-D-manno-octonic acid	HMDB
2-Keto-3-deoxyoctonate	HMDB
2-Keto-3-deoxyoctulosonic acid	HMDB
3-KDO	HMDB
3-Deoxy-2-octulosonic acid	HMDB
3-Deoxy-8-manno-oct-2-ulosonic acid	HMDB
3-Deoxy-D-manno-oct-2-ulosonic acid	HMDB
3-Deoxy-D-manno-octulosonic acid	HMDB
3-Deoxy-D-mannoctulosonate	HMDB
3-Deoxy-D-mannooctulosonate	HMDB
3-Deoxy-alpha-D-manno-2-octulosonic acid	HMDB
KDO CPD	HMDB
Ion(1-),(D)-isomer OF 2-keto-3-deoxyoctonate	HMDB
4,5,6,7,8-Pentahydroxy-2-oxooctanoate	HMDB

Chemical Formula

C₈H₁₄O₈

Average Molecular Weight

238.192

Monoisotopic Molecular Weight

238.068867411

IUPAC Name

4,5,6,7,8-pentahydroxy-2-oxooctanoic acid

Traditional Name

4,5,6,7,8-pentahydroxy-2-oxooctanoic acid

CAS Registry Number

Not Available

SMILES

OCC(O)C(O)C(O)C(O)CC(=O)C(O)=O

InChI Identifier

InChI=1S/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)

InChI Key

KYQCXUMVJGMDNG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Octose monosaccharide
Medium-chain keto acid
Sugar acid
Alpha-keto acid
Beta-hydroxy ketone
Monosaccharide
Keto acid
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Uronic acids (C01187 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.5	ALOGPS
logP	-3	ChemAxon
logS	-0.57	ALOGPS
pKa (Strongest Acidic)	2.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	48.24 m³·mol⁻¹	ChemAxon
Polarizability	20.76 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	146.652	30932474
DeepCCS	[M-H]-	144.294	30932474
DeepCCS	[M-2H]-	179.239	30932474
DeepCCS	[M+Na]+	154.803	30932474
AllCCS	[M+H]+	152.5	32859911
AllCCS	[M+H-H2O]+	149.1	32859911
AllCCS	[M+NH4]+	155.7	32859911
AllCCS	[M+Na]+	156.6	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	146.4	32859911
AllCCS	[M+HCOO]-	147.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.5632 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.83 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	647.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	299.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	27.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	74.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	293.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	248.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	738.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	602.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	47.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	900.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	256.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	668.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	379.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	414.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Keto-3-deoxy-D-manno-octulosonic acid	OCC(O)C(O)C(O)C(O)CC(=O)C(O)=O	4131.7	Standard polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid	OCC(O)C(O)C(O)C(O)CC(=O)C(O)=O	1929.5	Standard non polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid	OCC(O)C(O)C(O)C(O)CC(=O)C(O)=O	2149.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Keto-3-deoxy-D-manno-octulosonic acid,7TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2220.9	Semi standard non polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid,7TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2359.9	Standard non polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid,7TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2336.3	Standard polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid,5TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C(O)C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3356.5	Semi standard non polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid,5TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C(O)C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3029.6	Standard non polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid,5TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C(O)C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3008.2	Standard polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3307.3	Semi standard non polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3099.9	Standard non polar	33892256
Keto-3-deoxy-D-manno-octulosonic acid,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2892.3	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

794

KEGG Compound ID

C01187

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

817

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Keto-3-deoxy-D-manno-octulosonic acid (HMDB0244292)

MOL for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

3D MOL for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

3D SDF for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

3D-SDF for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

PDB for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

3D PDB for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

SMILES for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

INCHI for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

Structure for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

3D Structure for HMDB0244292 (Keto-3-deoxy-D-manno-octulosonic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized