Human Metabolome Database: Showing metabocard for 6-Hydroxy-R-phenprocoumon (HMDB0060886)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:05:17 UTC

Update Date

2017-12-07 18:16:25 UTC

HMDB ID

HMDB0060886

Secondary Accession Numbers

HMDB60886

Metabolite Identification

Common Name

6-Hydroxy-R-phenprocoumon

Description

6-Hydroxy-R-phenprocoumon is a metabolite of phenprocoumon. Phenprocoumon (marketed under the brand names Marcoumar, Marcumar and Falithrom) is an anticoagulant drug, a derivative of coumarin. It is a vitamin K antagonist that inhibits coagulation by blocking synthesis of coagulation factors II, VII, IX and X. It is used for the prophylaxis and treatment of thromboembolic disorders. Phenprocoumon is a 4-hydroxycoumarin and inhibits inhibits vitamin K epoxide reductase. (Wikipedia)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₄

Average Molecular Weight

296.3172

Monoisotopic Molecular Weight

296.104859

IUPAC Name

4,6-dihydroxy-3-[(1R)-1-phenylpropyl]-2H-chromen-2-one

Traditional Name

4,6-dihydroxy-3-[(1R)-1-phenylpropyl]chromen-2-one

CAS Registry Number

Not Available

SMILES

CC[C@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC(O)=C2

InChI Identifier

InChI=1S/C18H16O4/c1-2-13(11-6-4-3-5-7-11)16-17(20)14-10-12(19)8-9-15(14)22-18(16)21/h3-10,13,19-20H,2H2,1H3/t13-/m1/s1

InChI Key

BKRXPRMCBOAGQH-CYBMUJFWSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

4-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
Benzopyran
1-benzopyran
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Biological location:

Organ and components:

Subcellular:

Biofluid and excreta:

Role

Biological role:

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.036 g/L	ALOGPS
logP	3.86	ALOGPS
logP	3.43	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.04	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.62 m³·mol⁻¹	ChemAxon
Polarizability	31.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2490000000-b29394fd87c9a3c73465	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-3103900000-e75381dba724fe986e81	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-864da96a3b7d6c2a50a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0290000000-2957d9704b4b216de2e0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05br-2940000000-870e8cff7235ae5fcbab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-41d65172a20847834472	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0390000000-788acde47566e2fa21f7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-5940000000-87a53c199b5d5b6f138b	View in MoNA

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Location

Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Normal		details
Urine	Expected but not Quantified		Not Available	Not Available	Normal		details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91987769

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 6-Hydroxy-R-phenprocoumon (HMDB0060886)

Structure for HMDB0060886 (6-Hydroxy-R-phenprocoumon)