NAV

4-hydroxycoumarin

Identification

Generic Name
4-hydroxycoumarin
DrugBank Accession Number
DB03410
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 162.144
Monoisotopic: 162.031694053
Chemical Formula
C9H6O3
Synonyms
  • 4-coumarinol
  • 4-hydroxy-2-chromenone
  • 4-hydroxy-2H-1-benzopyran-2-one
  • 4-hydroxy-2H-benzo[b]pyran-2-one
  • 4-hydroxychromen-2-one
  • 4-hydroxycoumarin
  • Benzotetronic acid
External IDs
  • NSC-11889
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with 4-hydroxycoumarin.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with 4-hydroxycoumarin.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when 4-hydroxycoumarin is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with 4-hydroxycoumarin.
AcetaminophenAcetaminophen may increase the anticoagulant activities of 4-hydroxycoumarin.
Food Interactions
No interactions found.

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-benzopyran / 4-hydroxycoumarin / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Heteroaromatic compound / Hydrocarbon derivative / Lactone / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
hydroxycoumarin (CHEBI:40070)
Affected organisms
Not Available

Chemical Identifiers

UNII
X954ZLL2RD
CAS number
1076-38-6
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

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
Human Metabolome Database
HMDB0137904
PubChem Compound
54682930
PubChem Substance
46508501
ChemSpider
10254753
BindingDB
50055710
ChEBI
40070
ChEMBL
CHEMBL301141
ZINC
ZINC000018154848
PDBe Ligand
4HC
Wikipedia
4-Hydroxycoumarin
PDB Entries
1v5y / 6y1u / 6y1v

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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-MSsplash10-03yi-2900000000-cdddd338f0ad245ac008
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-a9106ff4ee0185919eb0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-894b4199257f16e02fe5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-7900000000-50d0936e7405702d2610
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-dbbf92b8d795f0c8ed4c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-d5088cb95d31affb361a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fr6-9200000000-59d3bf48b55ad6bfa7f4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-132.4354085
predicted
DarkChem Lite v0.1.0
[M-H]-132.5880085
predicted
DarkChem Lite v0.1.0
[M-H]-132.7245085
predicted
DarkChem Lite v0.1.0
[M-H]-123.85743
predicted
DeepCCS 1.0 (2019)
[M+H]+133.3669085
predicted
DarkChem Lite v0.1.0
[M+H]+133.4077085
predicted
DarkChem Lite v0.1.0
[M+H]+133.1246085
predicted
DarkChem Lite v0.1.0
[M+H]+127.68568
predicted
DeepCCS 1.0 (2019)
[M+Na]+132.5397085
predicted
DarkChem Lite v0.1.0
[M+Na]+132.6106085
predicted
DarkChem Lite v0.1.0
[M+Na]+136.78253
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Major NAD(P)H-flavin oxidoreductase
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51