| 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