Common Name |
7-Hydroxyoctanoic acid
Description |
7-Hydroxyoctanoic acid is a normal metabolite of medium-chain fatty acid oxidation, and is excreted in the urine as 7-hydroxyoctanoyl-beta-D-glucuronide (PMID 8799296 ), and have been found slightly elevated in the urine of persons with abnormal fatty acid metabolism (PMID 2094705 ).
Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms |
Value |
Source |
7-Hydroxy-octanoateHMDB
7-Hydroxy-octanoic acidHMDB
7-HydroxyoctanoateHMDB
Chemical Formlia |
C8H16O3
Average Molecliar Weight |
160.2108
Monoisotopic Molecliar Weight |
160.109944378
IUPAC Name |
7-hydroxyoctanoic acid
Traditional Name |
7-hydroxyoctanoic acid
CAS Registry Number |
17173-14-7
SMILES |
CC(O)CCCCCC(O)=O
InChI Identifier |
InChI=1S/C8H16O3/c1-7(9)5-3-2-4-6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
InChI Key |
OFCMTSZRXXFMBQ-UHFFFAOYSA-N
Chemical Taxonomy |
Description |
This compound belongs to the class of chemical entities known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
Kingdom |
Chemical entities
Super Class |
Organic compounds
Class |
Organic acids and derivatives
Sub Class |
Hydroxy acids and derivatives
Direct Parent |
Medium-chain hydroxy acids and derivatives
Alternative Parents |
Medium-chain fatty acids
Hydroxy fatty acids
Secondary alcohols
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Substituents |
Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound
Molecliar Framework |
Aliphatic acyclic compounds
External Descriptors |
Hydroxy fatty acids (LMFA01050229 )
Ontology |
Status |
Detected and Quantified
Origin |
Endogenous
Biofunction |
Not Available
Application |
Not Available
Cellliar locations |
Cytoplasm
Physical Properties |
State |
Solid
Experimental Properties |
Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties |
Property |
Value |
Source |
Water Solubility12.5 mg/mLALOGPS
logP1.33ALOGPS
logP1.24ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.02 m3·mol-1ChemAxon
Polarizability18.24 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
Spectra |
Spectra |
Spectrum Type |
Description |
Splash Key |
|
LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, N/A (Annotated)splash10-004j-5900000000-a85c06e01dbb9185392cView in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9000000000-6e04eb7529ce6e974d15View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, N/A (Annotated)splash10-0a4i-9000000000-539051793102de67657fView in MoNA
Biological Properties |
Cellliar Locations |
Cytoplasm
Biofluid Locations |
Urine
Tissue Location |
Not Available
Pathways |
Not Available
Normal Concentrations |
Not Available |
Abnormal Concentrations |
|
Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdlit (>18 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency
MetaGene
details
UrineDetected and Quantified152.00 (4.00-300.00) umol/mmol creatinineChildren (1-13 years old)BothMedium chain acyl-CoA dehydrogenase deficiency (MCAD)
MetaGene
details
Associated Disorders and Diseases |
Disease References |
Medium Chain Acyl-CoA Dehydrogenase Deficiency |
- MetaGene [Link]
Associated OMIM IDs |
201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
External Links |
DrugBank ID |
Not Available
DrugBank Metabolite ID |
Not Available
Phenol Explorer Compound ID |
Not Available
Phenol Explorer Metabolite ID |
Not Available
FoodDB ID |
FDB022069
KNApSAcK ID |
Not Available
Chemspider ID |
146647
KEGG Compound ID |
Not Available
BioCyc ID |
Not Available
BiGG ID |
Not Available
Wikipedia Link |
Not Available
NuGOwiki Link |
HMDB00486
Metagene Link |
HMDB00486
METLIN ID |
5473
PubChem Compound |
167627
PDB ID |
Not Available
ChEBI ID |
Not Available
Product: Impurity of Doxercalciferol
References |
Synthesis Reference |
Sugiyama, Noboru; Gasha, Taketoshi; Kashima, Choji. Macrocyclic dilactone. I. Synthesis of 7-hydroxyoctanoic acid dilactone. Bulletin of the Chemical Society of Japan (1967), 40(11), 02713-14. |
Material Safety Data Sheet (MSDS) |
Not Available |
General References |
- Pitt JJ: Gas chromatographic-mass spectrometric characterisation of unsaturated dicarboxylic acids in urine. J Chromatogr. 1990 Dec 14;534:182-9. [PubMed:2094705 ]
- Costa CC, Dorland L, Kroon M, Tavares de Almeida I, Jakobs C, Duran M: 3-, 6- and 7-hydroxyoctanoic acids are metabolites of medium-chain triglycerides and excreted in urine as glucuronides. J Mass Spectrom. 1996 Jun;31(6):633-8. [PubMed:8799296 ]
|
PMID: 17486140