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Showing metabocard for 3-Hydroxyisoheptanoic acid (HMDB0002207)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2023-02-21 17:16:16 UTC
HMDB IDHMDB0002207
Secondary Accession Numbers
  • HMDB02207
Metabolite Identification
Common Name3-Hydroxyisoheptanoic acid
Description3-Hydroxyisoheptanoic acid belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. 3-Hydroxyisoheptanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyisoheptanoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxyisoheptanoic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002207 (3-Hydroxyisoheptanoic acid)

  Mrv0541 02231219252D          

 10  9  0  0  0  0            999 V2000
   26.1343   -5.1301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2778   -3.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5632   -5.1301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1343   -4.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7053   -4.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4199   -3.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8488   -3.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9908   -3.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7053   -5.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5632   -4.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2 10  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
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3D MOL for HMDB0002207 (3-Hydroxyisoheptanoic acid)

HMDB0002207
     RDKit          3D
3-Hydroxyisoheptanoic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -2.1509   -1.1498    0.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -0.1650   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    1.2095    0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4188   -0.2477   -0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.0734   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -0.9535    0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281   -0.1063   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1979    0.0490    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235   -0.8789    0.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182    1.2728    0.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537   -2.2244    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312   -1.0190    0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222   -0.9791    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -0.3442   -1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6274    1.5492    0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2585    1.9482   -0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    1.0742    0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -1.1846   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    0.5557   -1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6435    0.9515    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -0.8208    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    0.5836   -1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475   -1.1416   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    2.0944    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 10 24  1  0
M  END
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3D SDF for HMDB0002207 (3-Hydroxyisoheptanoic acid)

  Mrv0541 02231219252D          

 10  9  0  0  0  0            999 V2000
   26.1343   -5.1301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2778   -3.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5632   -5.1301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1343   -4.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7053   -4.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4199   -3.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8488   -3.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9908   -3.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7053   -5.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5632   -4.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2 10  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002207

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O3/c1-5(2)3-6(8)4-7(9)10/h5-6,8H,3-4H2,1-2H3,(H,9,10)

> <INCHI_KEY>
SCAWECGFPWPHAR-UHFFFAOYSA-N

> <FORMULA>
C7H14O3

> <MOLECULAR_WEIGHT>
146.1843

> <EXACT_MASS>
146.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.821835404208088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-5-methylhexanoic acid

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
0.8671041569999995

> <ALOGPS_LOGS>
-0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.280442797222399

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.765313027492492

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8021102433447043

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
37.1377

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.90e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyisoheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002207 (3-Hydroxyisoheptanoic acid)

HMDB0002207
     RDKit          3D
3-Hydroxyisoheptanoic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -2.1509   -1.1498    0.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -0.1650   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    1.2095    0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4188   -0.2477   -0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.0734   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -0.9535    0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281   -0.1063   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1979    0.0490    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235   -0.8789    0.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182    1.2728    0.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537   -2.2244    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312   -1.0190    0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222   -0.9791    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -0.3442   -1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6274    1.5492    0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2585    1.9482   -0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    1.0742    0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -1.1846   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    0.5557   -1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6435    0.9515    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -0.8208    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    0.5836   -1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475   -1.1416   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9930    2.0944    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 10 24  1  0
M  END
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PDB for HMDB0002207 (3-Hydroxyisoheptanoic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      48.784  -9.576   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      52.785  -7.266   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      51.451  -9.576   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      48.784  -8.036   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      46.117  -8.036   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      47.450  -7.266   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      50.118  -7.266   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      44.783  -7.266   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      46.117  -9.576   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      51.451  -8.036   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    1    6    7                                                  
CONECT    5    6    8    9                                                  
CONECT    6    4    5                                                       
CONECT    7    4   10                                                       
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    2    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0002207 (3-Hydroxyisoheptanoic acid)

COMPND    HMDB0002207
HETATM    1  C1  UNL     1      -2.151  -1.150   0.636  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.786  -0.165  -0.420  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.195   1.210   0.078  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.419  -0.248  -0.956  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.715  -0.073  -0.031  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.827  -0.954   0.996  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.028  -0.106  -0.823  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.198   0.049   0.078  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.023  -0.879   0.322  1.00  0.00           O  
HETATM   10  O3  UNL     1       3.418   1.273   0.700  1.00  0.00           O  
HETATM   11  H1  UNL     1      -2.054  -2.224   0.305  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.231  -1.019   0.861  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.622  -0.979   1.595  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.499  -0.344  -1.289  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.627   1.549   0.959  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.259   1.948  -0.743  1.00  0.00           H  
HETATM   17  H7  UNL     1      -3.266   1.074   0.425  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.263  -1.185  -1.531  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.320   0.556  -1.743  1.00  0.00           H  
HETATM   20  H10 UNL     1       0.643   0.951   0.410  1.00  0.00           H  
HETATM   21  H11 UNL     1       1.691  -0.821   1.467  1.00  0.00           H  
HETATM   22  H12 UNL     1       2.007   0.584  -1.668  1.00  0.00           H  
HETATM   23  H13 UNL     1       2.147  -1.142  -1.285  1.00  0.00           H  
HETATM   24  H14 UNL     1       2.993   2.094   0.321  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4   14
CONECT    3   15   16   17
CONECT    4    5   18   19
CONECT    5    6    7   20
CONECT    6   21
CONECT    7    8   22   23
CONECT    8    9    9   10
CONECT   10   24
END
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SMILES for HMDB0002207 (3-Hydroxyisoheptanoic acid)

CC(C)CC(O)CC(O)=O
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INCHI for HMDB0002207 (3-Hydroxyisoheptanoic acid)

InChI=1S/C7H14O3/c1-5(2)3-6(8)4-7(9)10/h5-6,8H,3-4H2,1-2H3,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-HydroxyisoheptanoateGenerator
3-Hydroxy-5-methylhexanoateHMDB, Generator
3-Hydroxy-5-methylhexanoic acidHMDB
3-Hydroxyisoheptanoic acidMeSH
Chemical FormulaC7H14O3
Average Molecular Weight146.1843
Monoisotopic Molecular Weight146.094294314
IUPAC Name3-hydroxy-5-methylhexanoic acid
Traditional Name3-hydroxyisoheptanoic acid
CAS Registry Number40309-49-7
SMILES
CC(C)CC(O)CC(O)=O
InChI Identifier
InChI=1S/C7H14O3/c1-5(2)3-6(8)4-7(9)10/h5-6,8H,3-4H2,1-2H3,(H,9,10)
InChI KeySCAWECGFPWPHAR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022907
KNApSAcK IDNot Available
Chemspider ID168187
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6547
PubChem Compound193804
PDB IDNot Available
ChEBI ID165406
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAnnunziata, Rita; Cinquini, Mauro; Gilardi, Amilcare. Optically active 2-(arylsulfinylmethyl)-oxazolines, chiral enol acetate equivalents in aldol-type condensations. Synthesis (1983), (12), 1016-17.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divry P, Vianey-Liaud C, Cotte J: Routine gas chromatographic/mass spectrometric analysis of urinary organic acids. Results over a three-year period. Biomed Environ Mass Spectrom. 1987 Nov;14(11):663-8. [PubMed:2962675 ]
  2. Lehnert W: 3-Hydroxyisoheptanoic acid: a new metabolite in isovaleric acidemia. Clin Chim Acta. 1981 Jun 2;113(1):101-3. [PubMed:7237839 ]