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Showing metabocard for Hydroxyoctanoic acid (HMDB0000711)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:05 UTC
HMDB IDHMDB0000711
Secondary Accession Numbers
  • HMDB00711
Metabolite Identification
Common NameHydroxyoctanoic acid
DescriptionHydroxyoctanoic acid, also known as a-hydroxyoctanoate or 2-hydroxycaprylate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a small amount of articles have been published on Hydroxyoctanoic acid.
Structure
Data?1676999705
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000711 (Hydroxyoctanoic acid)

  Mrv1652305271900162D          

 11 10  0  0  0  0            999 V2000
   26.3604  -12.6931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7893  -11.8681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0749  -10.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9314  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2169  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5025  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6458  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7879  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3604  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0734  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0749  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000711 (Hydroxyoctanoic acid)

HMDB0000711
     RDKit          3D
Hydroxyoctanoic acid
 27 26  0  0  0  0  0  0  0  0999 V2000
   -4.5402   -0.1620   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635    0.5225   -0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650   -0.2793   -0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.4066   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -0.3243   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    0.4212   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -0.2810   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925   -1.5644    0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    0.5047    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2656    1.7115   -0.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367   -0.0827    0.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5643   -1.1658   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5002   -0.2523   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3974    0.4695   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1994    1.5594   -0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2902    0.5622    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -1.3080   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -0.3397   -1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    0.4620    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295    1.4553   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -1.3022    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -0.5827   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696    0.4802    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    1.4388   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -0.2853   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -2.2702   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9047    0.2059    1.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
M  END
Download

3D SDF for HMDB0000711 (Hydroxyoctanoic acid)

  Mrv1652305271900162D          

 11 10  0  0  0  0            999 V2000
   26.3604  -12.6931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7893  -11.8681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0749  -10.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9314  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2169  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5025  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6458  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7879  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3604  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0734  -11.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0749  -11.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000711

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)

> <INCHI_KEY>
JKRDADVRIYVCCY-UHFFFAOYSA-N

> <FORMULA>
C8H16O3

> <MOLECULAR_WEIGHT>
160.2108

> <EXACT_MASS>
160.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.007170726296977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxyoctanoic acid

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.828967537

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.284148892109581

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.422499319236623

> <JCHEM_PKA_STRONGEST_BASIC>
-3.797528711914386

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
41.767799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyoctanoate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000711 (Hydroxyoctanoic acid)

HMDB0000711
     RDKit          3D
Hydroxyoctanoic acid
 27 26  0  0  0  0  0  0  0  0999 V2000
   -4.5402   -0.1620   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635    0.5225   -0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650   -0.2793   -0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8003    0.4066   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -0.3243   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    0.4212   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -0.2810   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9925   -1.5644    0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    0.5047    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2656    1.7115   -0.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367   -0.0827    0.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5643   -1.1658   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5002   -0.2523   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3974    0.4695   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1994    1.5594   -0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2902    0.5622    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -1.3080   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -0.3397   -1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    0.4620    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295    1.4553   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -1.3022    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -0.5827   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696    0.4802    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    1.4388   -0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769   -0.2853   -1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -2.2702   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9047    0.2059    1.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
M  END
Download

PDB for HMDB0000711 (Hydroxyoctanoic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      49.206 -23.694   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      51.873 -22.154   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      50.540 -19.844   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      46.539 -22.154   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      45.205 -21.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      43.871 -22.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.872 -21.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.537 -21.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.206 -22.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      41.204 -22.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.540 -21.384   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    5    7                                                       
CONECT    5    4    6                                                       
CONECT    6    5    8                                                       
CONECT    7    4    9                                                       
CONECT    8    6   10                                                       
CONECT    9    1    7   11                                                  
CONECT   10    8                                                            
CONECT   11    2    3    9                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0000711 (Hydroxyoctanoic acid)

COMPND    HMDB0000711
HETATM    1  C1  UNL     1      -4.540  -0.162  -0.567  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.263   0.523  -0.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.065  -0.279  -0.578  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.800   0.407  -0.124  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.436  -0.324  -0.544  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.660   0.421  -0.054  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.938  -0.281  -0.456  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.992  -1.564   0.072  1.00  0.00           O  
HETATM    9  C8  UNL     1       4.062   0.505   0.104  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.266   1.711  -0.198  1.00  0.00           O  
HETATM   11  O3  UNL     1       4.937  -0.083   0.993  1.00  0.00           O  
HETATM   12  H1  UNL     1      -4.564  -1.166  -0.143  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.500  -0.252  -1.663  1.00  0.00           H  
HETATM   14  H3  UNL     1      -5.397   0.469  -0.288  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.199   1.559  -0.504  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.290   0.562   0.987  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.143  -1.308  -0.173  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.137  -0.340  -1.682  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.806   0.462   0.976  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.830   1.455  -0.490  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.436  -1.302   0.020  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.492  -0.583  -1.600  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.670   0.480   1.053  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.657   1.439  -0.463  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.077  -0.285  -1.561  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.009  -2.270  -0.608  1.00  0.00           H  
HETATM   27  H16 UNL     1       5.905   0.206   1.083  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    9   25
CONECT    8   26
CONECT    9   10   10   11
CONECT   11   27
END
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SMILES for HMDB0000711 (Hydroxyoctanoic acid)

CCCCCCC(O)C(O)=O
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INCHI for HMDB0000711 (Hydroxyoctanoic acid)

InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H16O3
Average Molecular Weight160.2108
Monoisotopic Molecular Weight160.109944378
IUPAC Name2-hydroxyoctanoic acid
Traditional Namehydroxyoctanoate
CAS Registry Number617-73-2
SMILES
CCCCCCC(O)C(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
InChI KeyJKRDADVRIYVCCY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point70 °CNot Available
Boiling Point289.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility927 mg/mLNot Available
LogP1.960 (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
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022197
KNApSAcK IDNot Available
Chemspider ID84994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5679
PubChem Compound94180
PDB IDNot Available
ChEBI ID86543
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1447721
References
Synthesis ReferenceSakaki, Keiji; Hara, Shigeki; Itoh, Naotsugu. Optical resolution of racemic 2-hydroxy octanoic acid using biphasic enzyme membrane reactor. Desalination (2002), 149(1-3), 247-252.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jones JM, Morrell JC, Gould SJ: Identification and characterization of HAOX1, HAOX2, and HAOX3, three human peroxisomal 2-hydroxy acid oxidases. J Biol Chem. 2000 Apr 28;275(17):12590-7. [PubMed:10777549 ]
  2. Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5. [PubMed:2044590 ]