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Record Information
Version3.6
Creation Date2006-08-13 02:37:06 UTC
Update Date2016-02-11 01:06:24 UTC
HMDB IDHMDB03654
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Coumaryl alcohol
Description4-Coumaryl alcohol is a substrate for NAD(P)H dehydrogenase 1.
Structure
Thumb
Synonyms
ValueSource
4-Hydroxycinnamyl alcoholChEBI
P-Coumaryl alcoholChEBI
3-(4-Hydroxyphenyl)-1-propaneHMDB
3-OHPPHMDB
4-CoumarinolHMDB
4-Hydroxy-2H-1-benzopyran-2-oneHMDB
4-Hydroxy-2H-chromen-2-oneHMDB
4-HydroxycoumarinHMDB
4-HydroxycoumarineHMDB
BenzotetronateHMDB
Benzotetronic acidHMDB
Hydroxy coumarinHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Name4-[(1E)-3-hydroxyprop-1-en-1-yl]phenol
Traditional Nameparacoumaryl alcohol
CAS Registry Number1076-38-6
SMILES
OC\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
InChI KeyInChIKey=PTNLHDGQWUGONS-OWOJBTEDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamyl alcohols
Sub ClassNot Available
Direct ParentCinnamyl alcohols
Alternative Parents
Substituents
  • Cinnamyl alcohol
  • Phenylpropene
  • Styrene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point213.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.97 mg/mLALOGPS
logP1.55ALOGPS
logP1.51ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.17 m3·mol-1ChemAxon
Polarizability16.35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Location
  • Testes
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03410
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID642
FoodDB IDFDB010971
KNApSAcK IDNot Available
Chemspider ID4444166
KEGG Compound IDC02646
BioCyc IDNot Available
BiGG ID2299830
Wikipedia Link4-Hydroxycoumarin
NuGOwiki LinkHMDB03654
Metagene LinkHMDB03654
METLIN ID6971
PubChem Compound5280535
PDB IDNot Available
ChEBI ID64555
References
Synthesis ReferenceTakahashi, Yukio; Kato, Keiichi; Kubota, Koichi. One-pot preparation of high-purity 4-hydroxycoumarin. Jpn. Kokai Tokkyo Koho (2005), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Maurer HH, Arlt JW: Detection of 4-hydroxycoumarin anticoagulants and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. J Chromatogr B Biomed Sci Appl. 1998 Sep 4;714(2):181-95. [9766858 ]
  2. Janssen LH, Van Wilgenburg MT, Wilting J: Human serum albumin as an allosteric two-state protein. Evidence from effects of calcium and warfarin on proton binding behaviour. Biochim Biophys Acta. 1981 Jul 28;669(2):244-50. [7284438 ]
  3. LE Lain R, Barrell KJ, Saeed GS, Nicholls PJ, Simons C, Kirby A, Smith HJ: Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme. J Enzyme Inhib Med Chem. 2002 Apr;17(2):93-100. [12420755 ]
  4. Vorum H, Fisker K, Brodersen R: High-affinity binding of two molecules of warfarin and phenprocoumon to human serum albumin. Biochim Biophys Acta. 1994 Apr 13;1205(2):178-82. [8155695 ]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
May contribute to airway host defense against infection.
Gene Name:
LPO
Uniprot ID:
P22079
Molecular weight:
70983.6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
Reactions
4-Coumaryl alcohol → p-Hydroxyphenyl lignindetails
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
General function:
Involved in peroxidase activity
Specific function:
Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
Gene Name:
EPX
Uniprot ID:
P11678
Molecular weight:
81039.5