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Showing metabocard for 6-Hydroxyhexanoic acid (HMDB0012843)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-07-25 00:08:24 UTC
Update Date2023-02-21 17:17:50 UTC
HMDB IDHMDB0012843
Secondary Accession Numbers
  • HMDB12843
Metabolite Identification
Common Name6-Hydroxyhexanoic acid
Description6-Hydroxyhexanoate was identified as the immediate product of hexanoate w-hydroxylation by whole cells and was further oxidized into adipic acid and an unexpected metabolite identified as 2-tetrahydrofuranacetic acid. This same metabolite, together with adipic acid, was also detected when similarly induced cells were incubated with hexanoate or 1,6-hexanediol, but not with 6-oxohexanoate (adipic semialdehyde).Cells grown on hexanoate and incubated with 6-hydroxyhexanoate were also found to accumulate 2-tetrahydrofuranacetic acid, which was not further degraded. Utilization of 6-hydroxyhexanoate for growth was restricted to those organisms also able to utilize adipate. Similar observations were made with 1,6-hexanediol serving as the carbon source and cells obtained from one organism,Pseudomonas aeruginosa PAO, grown either on 1,6-hexanediol or 6-hydroxyhexanoate,were found to be well induced for both 6-oxohexanoate and adipate oxidation. The results indicate that 6-hydroxyhexanoate and 1,6-hexanediol are susceptible to both 1B- and w-oxidative attack; however, the former pathway appears to be of no physiological significance since it generates 2-tetrahydrofuranacetic acid as a nonmetabolizable intermediate, making w-oxidation via adipate the exclusive pathway for degradation.
Structure
Data?1676999870
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012843 (6-Hydroxyhexanoic acid)

  Mrv1652303102016462D          

  9  8  0  0  0  0            999 V2000
   11.7081  -15.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1206  -14.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8831  -15.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9456  -14.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4707  -15.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3580  -13.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6457  -15.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1830  -13.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9456  -13.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  2  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
M  END
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3D MOL for HMDB0012843 (6-Hydroxyhexanoic acid)

HMDB0012843
     RDKit          3D
6-Hydroxyhexanoic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.2174    1.5033    0.0209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3579    0.2929   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5899   -0.3302   -0.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2200   -0.4947   -0.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -0.9997    0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2678    0.1119    1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067    1.0525    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753    0.3807   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510   -0.2272    0.5119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407   -0.4438    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163   -1.3839   -1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6653    0.1191   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4037   -1.6756   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -1.5927    0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804    0.7087    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8064   -0.2983    1.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498    1.8740    0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.4973   -0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437    1.1997   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -0.3133   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7467   -0.9808    1.0021 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
  7  8  1  0
  8  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
M  END
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3D SDF for HMDB0012843 (6-Hydroxyhexanoic acid)

  Mrv1652303102016462D          

  9  8  0  0  0  0            999 V2000
   11.7081  -15.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1206  -14.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8831  -15.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9456  -14.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4707  -15.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3580  -13.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6457  -15.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1830  -13.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9456  -13.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  2  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012843

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c7-5-3-1-2-4-6(8)9/h7H,1-5H2,(H,8,9)

> <INCHI_KEY>
IWHLYPDWHHPVAA-UHFFFAOYSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.1577

> <EXACT_MASS>
132.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.243634575644695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxyhexanoic acid

> <ALOGPS_LOGP>
0.29

> <JCHEM_LOGP>
0.37421751100000017

> <ALOGPS_LOGS>
-0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.843935536859917

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.710101883850394

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922627018970158

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
33.0023

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.97e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxyhexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0012843 (6-Hydroxyhexanoic acid)

HMDB0012843
     RDKit          3D
6-Hydroxyhexanoic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.2174    1.5033    0.0209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3579    0.2929   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5899   -0.3302   -0.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2200   -0.4947   -0.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -0.9997    0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2678    0.1119    1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067    1.0525    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2753    0.3807   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510   -0.2272    0.5119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407   -0.4438    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163   -1.3839   -1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6653    0.1191   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4037   -1.6756   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -1.5927    0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804    0.7087    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8064   -0.2983    1.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498    1.8740    0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829    1.4973   -0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437    1.1997   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -0.3133   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7467   -0.9808    1.0021 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
  7  8  1  0
  8  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
M  END
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PDB for HMDB0012843 (6-Hydroxyhexanoic acid)

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      21.855 -28.354   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.625 -27.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.315 -28.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.165 -27.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.545 -29.688   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.935 -25.687   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      18.005 -29.688   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      26.475 -25.687   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.165 -24.353   0.000  0.00  0.00           O+0
CONECT    1    3    2                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0012843 (6-Hydroxyhexanoic acid)

COMPND    HMDB0012843
HETATM    1  O1  UNL     1      -2.217   1.503   0.021  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.358   0.293  -0.291  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.590  -0.330  -0.161  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.220  -0.495  -0.803  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.328  -1.000   0.298  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.268   0.112   1.119  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.107   1.053   0.320  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.275   0.381  -0.355  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.151  -0.227   0.512  1.00  0.00           O  
HETATM   10  H1  UNL     1      -3.941  -0.444   0.801  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.616  -1.384  -1.332  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.665   0.119  -1.547  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.404  -1.676  -0.139  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.982  -1.593   0.988  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.580   0.709   1.541  1.00  0.00           H  
HETATM   16  H7  UNL     1       0.806  -0.298   1.989  1.00  0.00           H  
HETATM   17  H8  UNL     1       1.450   1.874   0.975  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.483   1.497  -0.484  1.00  0.00           H  
HETATM   19  H10 UNL     1       2.844   1.200  -0.875  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.964  -0.313  -1.153  1.00  0.00           H  
HETATM   21  H12 UNL     1       2.747  -0.981   1.002  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5   11   12
CONECT    5    6   13   14
CONECT    6    7   15   16
CONECT    7    8   17   18
CONECT    8    9   19   20
CONECT    9   21
END
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SMILES for HMDB0012843 (6-Hydroxyhexanoic acid)

OCCCCCC(O)=O
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INCHI for HMDB0012843 (6-Hydroxyhexanoic acid)

InChI=1S/C6H12O3/c7-5-3-1-2-4-6(8)9/h7H,1-5H2,(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
5-CarboxypentanolChEBI
5-Hydroxypentanecarboxylic acidChEBI
6-Hydroxy caproic acidChEBI
6-Hydroxycaproic acidChEBI
6-HydroxyhexanoateChEBI
epsilon-Hydroxycaproic acidChEBI
epsilon-Hydroxyhexanoic acidChEBI
5-HydroxypentanecarboxylateGenerator
6-Hydroxy caproateGenerator
6-HydroxycaproateGenerator
epsilon-HydroxycaproateGenerator
epsilon-HydroxyhexanoateGenerator
6-Hydroxyhexanoic acidGenerator
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name6-hydroxyhexanoic acid
Traditional Name6-hydroxyhexanoic acid
CAS Registry Number1191-25-9
SMILES
OCCCCCC(O)=O
InChI Identifier
InChI=1S/C6H12O3/c7-5-3-1-2-4-6(8)9/h7H,1-5H2,(H,8,9)
InChI KeyIWHLYPDWHHPVAA-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
  • Hydroxy fatty acid
  • Straight chain fatty acid
  • Fatty acyl
  • Fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point272.00 to 273.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility228700 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.191 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.0489 +/- 0.142 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.0718 +/- 0.144 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.315 +/- 0.250 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.358 +/- 0.404 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029184
KNApSAcK IDNot Available
Chemspider ID13835
KEGG Compound IDC06103
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14490
PDB IDNot Available
ChEBI ID17869
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1473761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Alcohol dehydrogenase [NADP(+)]
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a variety of aromatic and aliphatic aldehydes to their corresponding alcohols. Catalyzes the reduction of mevaldate to mevalonic acid and of glyceraldehyde to glycerol. Has broad substrate specificity. In vitro substrates include succinic semialdehyde, 4-nitrobenzaldehyde, 1,2-naphthoquinone, methylglyoxal, and D-glucuronic acid. Plays a role in the activation of procarcinogens, such as polycyclic aromatic hydrocarbon trans-dihydrodiols, and in the metabolism of various xenobiotics and drugs, including the anthracyclines doxorubicin (DOX) and daunorubicin (DAUN).
Gene Name:
AKR1A1
Uniprot ID:
P14550
Molecular weight:
36572.71
Reactions
6-Hydroxyhexanoic acid + NADP → Adipate semialdehyde + NADPH + Hydrogen Iondetails
Enzyme Details
2. Regucalcin
General function:
Involved in calcium ion binding
Specific function:
Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:
RGN
Uniprot ID:
Q15493
Molecular weight:
33252.53
Reactions
epsilon-Caprolactone + Water → 6-Hydroxyhexanoic aciddetails