Identification

Name
4-hydroxycoumarin
Accession Number
DB03410  (EXPT00215)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 4-coumarinol
  • 4-Hydroxy-1-Benzopyran-2-One
  • 4-hydroxy-2H-1-benzopyran-2-one
  • 4-hydroxychromen-2-one
  • benzotetronic acid
External IDs
NSC-11889
Categories
UNII
X954ZLL2RD
CAS number
1076-38-6
Weight
Average: 162.144
Monoisotopic: 162.031694053
Chemical Formula
C9H6O3
InChI Key
VXIXUWQIVKSKSA-UHFFFAOYSA-N
InChI
InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
IUPAC Name
4-hydroxy-2H-chromen-2-one
SMILES
OC1=CC(=O)OC2=CC=CC=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMajor NAD(P)H-flavin oxidoreductaseNot AvailableVibrio fischeri
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with 4-hydroxycoumarin.
AcenocoumarolAcenocoumarol may increase the anticoagulant activities of 4-hydroxycoumarin.
AcetaminophenAcetaminophen may increase the anticoagulant activities of 4-hydroxycoumarin.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of 4-hydroxycoumarin.
AlclometasoneThe metabolism of 4-hydroxycoumarin can be decreased when combined with Alclometasone.
AlfuzosinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Alfuzosin.
AlteplaseThe risk or severity of bleeding can be increased when Alteplase is combined with 4-hydroxycoumarin.
AmcinonideThe metabolism of 4-hydroxycoumarin can be decreased when combined with Amcinonide.
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of 4-hydroxycoumarin.
AmiodaroneThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Amiodarone.
Food Interactions
Not Available

References

Synthesis Reference

Nasri W. Badran, "Microcrystalline 3-(alpha-acetonylbenzyl)-4-hydroxycoumarin (warfarin) and methods of making." U.S. Patent US4113744, issued April, 1960.

US4113744
General References
Not Available
External Links
Human Metabolome Database
HMDB0137904
PubChem Compound
54682930
PubChem Substance
46508501
ChemSpider
10254753
BindingDB
50055710
ChEBI
40070
ChEMBL
CHEMBL301141
HET
4HC
Wikipedia
4-Hydroxycoumarin
PDB Entries
1v5y

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)213.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.78 mg/mLALOGPS
logP1.01ALOGPS
logP1.03ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.3ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.44 m3·mol-1ChemAxon
Polarizability15.24 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9903
Blood Brain Barrier+0.8971
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.6269
P-glycoprotein inhibitor INon-inhibitor0.9317
P-glycoprotein inhibitor IINon-inhibitor0.9336
Renal organic cation transporterNon-inhibitor0.8728
CYP450 2C9 substrateNon-substrate0.7808
CYP450 2D6 substrateNon-substrate0.9335
CYP450 3A4 substrateNon-substrate0.7528
CYP450 1A2 substrateInhibitor0.8298
CYP450 2C9 inhibitorNon-inhibitor0.87
CYP450 2D6 inhibitorNon-inhibitor0.942
CYP450 2C19 inhibitorNon-inhibitor0.7922
CYP450 3A4 inhibitorNon-inhibitor0.838
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9069
Ames testNon AMES toxic0.9448
CarcinogenicityNon-carcinogens0.9263
BiodegradationNot ready biodegradable0.5514
Rat acute toxicity2.2141 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9366
hERG inhibition (predictor II)Non-inhibitor0.9674
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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
1-benzopyrans / Pyranones and derivatives / Benzenoids / Vinylogous acids / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
4-hydroxycoumarin / Benzopyran / 1-benzopyran / Pyranone / Pyran / Benzenoid / Heteroaromatic compound / Vinylogous acid / Lactone / Oxacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
hydroxycoumarin (CHEBI:40070)

Targets

Kind
Protein
Organism
Vibrio fischeri
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Involved in bioluminescence. It is a good supplier of reduced flavin mononucleotide (FMNH2) to the bioluminescence reaction. Major FMN reductase. It is capable of using both NADH and NADPH as elect...
Gene Name
Not Available
Uniprot ID
P46072
Uniprot Name
Major NAD(P)H-flavin oxidoreductase
Molecular Weight
24720.685 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Sotaniemi EA, Rautio A, Backstrom M, Arvela P, Pelkonen O: CYP3A4 and CYP2A6 activities marked by the metabolism of lignocaine and coumarin in patients with liver and kidney diseases and epileptic patients. Br J Clin Pharmacol. 1995 Jan;39(1):71-6. [PubMed:7756103]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 05:06