| Common Name |
3 Hydroxycoumarin
| Description |
3 hydroxycoumarin is a metabolite of coumarin. In particliar, coumarin is metabolized by CYP3A4 to form 3-hydroxycoumarin (PMID 17286538 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
3-Hydroxy-2-benzopyroneHMDB
3-Hydroxy-2H-1-benzopyran-2-oneHMDB
3-Hydroxy-coumarinHMDB
3-HydroxycoumarinHMDB
O-Hydroxyphenylpyruvic acid lactoneHMDB
| Chemical Formlia |
C9H6O3
| Average Molecliar Weight |
162.1421
| Monoisotopic Molecliar Weight |
162.031694058
| IUPAC Name |
3-hydroxy-2H-chromen-2-one
| Traditional Name |
3 hydroxycoumarin
| CAS Registry Number |
939-19-5
| SMILES |
OC1=CC2=CC=CC=C2OC1=O
| InChI Identifier |
InChI=1S/C9H6O3/c10-7-5-6-3-1-2-4-8(6)12-9(7)11/h1-5,10H
| InChI Key |
MJKVTPMWOKAVMS-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Phenylpropanoids and polyketides
| Sub Class |
Coumarins and derivatives
| Direct Parent |
Hydroxycoumarins
| Alternative Parents |
1-benzopyrans
Pyranones and derivatives
Benzenoids
Heteroaromatic compounds
Lactones
Oxacyclic compounds
Organooxygen compounds
Organic oxides
Hydrocarbon derivatives
| Substituents |
Hydroxycoumarin
1-benzopyran
Benzopyran
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| 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 Solubility2.23 mg/mLALOGPS
logP1.09ALOGPS
logP1.54ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.8ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.52 m3·mol-1ChemAxon
Polarizability15.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-03di-0900000000-7d1955fa95d57eadbb55View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-03di-0900000000-6f0cd6d597527cbb163eView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-066r-5900000000-b0999ba2a570cafbd94bView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-03di-0900000000-bb3cef2e499cd852c2d7View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-03di-0900000000-6946524fd577f85fc413View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0a4i-2900000000-68c22e3edc0cfd0c0975View in MoNA
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| 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 |
FDB022869
| KNApSAcK ID |
Not Available
| Chemspider ID |
13061
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02149
| Metagene Link |
HMDB02149
| METLIN ID |
6512
| PubChem Compound |
13650
| PDB ID |
Not Available
| ChEBI ID |
349245
Product: Amentoflavone
References |
| Synthesis Reference |
Sun, Yi-feng; Song, Hua-can; Xu, Xiao-hang; Huang, Meng-wei; Xu, Zun-le. Synthesis of 3-aminocoumarin and its derivatives. Zhongshan Daxue Xuebao, Ziran Kexueban (2002), 41(6), 42-45. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- ARMSTRONG MD, SHAW KN, WALL PE: The phenolic acids of human urine; paper chromatography of phenolic acids. J Biol Chem. 1956 Jan;218(1):293-303. [PubMed:13278337 ]
- Farinola N, Piller NB: CYP2A6 polymorphisms: is there a role for pharmacogenomics in preventing coumarin-induced hepatotoxicity in lymphedema patients? Pharmacogenomics. 2007 Feb;8(2):151-8. [PubMed:17286538 ]
|
PMID: 14623770