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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2021-09-14 15:47:52 UTC
HMDB IDHMDB0002203
Secondary Accession Numbers
  • HMDB02203
Metabolite Identification
Common Name3-Hydroxycapric acid
Description3-Hydroxycapric acid (CAS: 14292-26-3) is a normally occurring carboxylic acid in human blood plasma. Medium- and long-chain 3-hydroxymonocarboxylic acids represent intermediates in the beta-oxidation of fatty acids. They accumulate in the plasma of patients with an inherited deficiency of long-chain 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35) (PMID: 1912723 ). 3-Hydroxyacyl-CoA dehydrogenase (HADH) deficiency has been described in diverse clinical cases: juvenile-onset recurrent myoglobinuria, hypoketotic hypoglycemic encephalopathy, hypertrophic/dilatative cardiomyopathy, sudden infant death, and fulminant hepatic failure (OMIM: 231530 ). 3-Hydroxycapric acid has some shape-transforming action on the membrane of intact human erythrocytes (PMID: 7318031 ).
Structure
Data?1582752235
Synonyms
ValueSource
3-HydroxycaprateGenerator
(S)-3-HydroxydecanoateHMDB
(+)-3-HydroxydecanoateHMDB
(+)-3-Hydroxydecanoic acidHMDB
(3S)-3-HydroxydecanoateHMDB
(3S)-3-Hydroxydecanoic acidHMDB
(±)-3-hydroxydecanoateHMDB
(±)-3-hydroxydecanoic acidHMDB
3(S)-HydroxydecanoateHMDB
3(S)-Hydroxydecanoic acidHMDB
3-HydroxidecanoateHMDB
3-Hydroxidecanoic acidHMDB
3-HydroxydecanoateHMDB
3-Hydroxydecanoic acidHMDB
FA(10:0(3-OH))HMDB
FA(10:0(3S-OH))HMDB
L-beta-HydroxydecanoateHMDB
L-beta-Hydroxydecanoic acidHMDB
L-Β-hydroxydecanoateHMDB
L-Β-hydroxydecanoic acidHMDB
S-3-HydroxydecanoateHMDB
S-3-Hydroxydecanoic acidHMDB
beta-HydroxycaprateHMDB
beta-Hydroxycapric acidHMDB
beta-HydroxydecanoateHMDB
beta-Hydroxydecanoic acidHMDB
Β-hydroxycaprateHMDB
Β-hydroxycapric acidHMDB
Β-hydroxydecanoateHMDB
Β-hydroxydecanoic acidHMDB
3-Hydroxycapric acidHMDB
Chemical FormulaC10H20O3
Average Molecular Weight188.267
Monoisotopic Molecular Weight188.141244504
IUPAC Name(3S)-3-hydroxydecanoic acid
Traditional NameS-3-hydroxydecanoic acid
CAS Registry Number19526-23-9
SMILES
CCCCCCC[C@H](O)CC(O)=O
InChI Identifier
InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m0/s1
InChI KeyFYSSBMZUBSBFJL-VIFPVBQESA-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
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.74 g/LALOGPS
logP10(2.6) g/LALOGPS
logP10(2.36) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity50.99 m³·mol⁻¹ChemAxon
Polarizability22.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxycapric acid,1TMS,#1CCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C1582.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxycapric acid,1TMS,#2CCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C1570.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxycapric acid,2TMS,#1CCCCCCC[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1665.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxycapric acid,1TBDMS,#1CCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C1804.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxycapric acid,1TBDMS,#2CCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C1799.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxycapric acid,2TBDMS,#1CCCCCCC[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2122.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Hydroxycapric acid GC-MS (2 TMS)splash10-0f89-3950000000-4dc7506e884d7c6679d52019-10-24HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Hydroxycapric acid GC-MS (Non-derivatized)splash10-0f89-3950000000-4dc7506e884d7c6679d52019-10-24HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxycapric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Hydroxycapric acid LC-ESI-IT , negative-QTOFsplash10-0a4i-9000000000-616c6c1304ee3dc8333d2019-10-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 10V, Negative-QTOFsplash10-000i-2900000000-b48a55f35e3a261db7a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 20V, Negative-QTOFsplash10-0a4i-9400000000-9bf57a4f1bdff00e64dc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 40V, Negative-QTOFsplash10-0006-9000000000-24256337cd6db4163a772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 10V, Positive-QTOFsplash10-052r-9800000000-05fd88a0d973888af6c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 20V, Positive-QTOFsplash10-0a4i-9000000000-6e5509a032d59c16205c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 40V, Positive-QTOFsplash10-0a4l-9000000000-2cfe9add86e448abe6752021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.00540 +/- 5.405 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified5.405 +/- 9.609 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified29.426 +/- 23.421 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified31.829 +/- 13.212 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
UrineDetected and Quantified88.279 +/- 75.668 umol/mmol creatinineChildren (1-13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and QuantifiedND-25 uMChildren (1-13 years old)Male3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency 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 and Quantified171.754-696.0255 umol/mmol creatinineInfant (0-1 year old)Not Specified3-Hydroxydicarboxylic aciduria details
Associated Disorders and Diseases
Disease References
3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency
  1. Thompson GN, Hsu BY, Pitt JJ, Treacy E, Stanley CA: Fasting hypoketotic coma in a child with deficiency of mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase. N Engl J Med. 1997 Oct 23;337(17):1203-7. doi: 10.1056/NEJM199710233371704. [PubMed:9337379 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  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 ]
3-Hydroxydicarboxylic aciduria
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82. [PubMed:1870421 ]
  2. Hagenfeldt L, von Dobeln U, Holme E, Alm J, Brandberg G, Enocksson E, Lindeberg L: 3-Hydroxydicarboxylic aciduria--a fatty acid oxidation defect with severe prognosis. J Pediatr. 1990 Mar;116(3):387-92. [PubMed:2308028 ]
Associated OMIM IDs
  • 605911 (3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency)
  • 114500 (Colorectal cancer)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022904
KNApSAcK IDNot Available
Chemspider ID4472224
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMyrmicacin
METLIN ID6544
PubChem Compound5312799
PDB IDNot Available
ChEBI ID37371
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKondo, Kiyoshi; Ryu, Yuchin. 3-Hydroxydecanoic acid. Jpn. Kokai Tokkyo Koho (1972), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Grupe A, Spiteller G: New polar acid metabolites in human urine. J Chromatogr. 1981 Dec 11;226(2):301-14. [PubMed:7320161 ]
  2. Dorland L, Ketting D, Bruinvis L, Duran M: Medium- and long-chain 3-hydroxymonocarboxylic acids: analysis by gas chromatography combined with mass spectrometry. Biomed Chromatogr. 1991 Jul;5(4):161-4. [PubMed:1912723 ]
  3. Kanaho Y, Sato T, Fujii T, Iwanami Y, Iwadare T, Orito K: Shape-transforming action of myrmicacin (3-hydroxydecanoic acid) and some related compounds on the membrane of intact human erythrocytes. Chem Pharm Bull (Tokyo). 1981 Oct;29(10):3063-6. [PubMed:7318031 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]