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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 02:37:06 UTC
Update Date2019-01-11 19:17:42 UTC
HMDB IDHMDB0003654
Secondary Accession Numbers
  • HMDB03654
Metabolite Identification
Common Name4-Coumaryl alcohol
Description4-Coumaryl alcohol is a substrate for NAD(P)H dehydrogenase 1.
Structure
Data?1547234262
Synonyms
ValueSource
(e)-4-Coumaryl alcoholChEBI
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
trans-3-(4'-Hydroxyphenyl)-2-propenoic acidMeSH
trans-HPPAMeSH
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 KeyPTNLHDGQWUGONS-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
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.17 m³·mol⁻¹ChemAxon
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0l1i-2900000000-35b232588497df392bccView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fu-9360000000-71f6e35237794477c995View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0900000000-d0aa38e43ffe69c65dceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-f35b26b4169e49f89651View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9600000000-feffeb0ec4d7bfd7e421View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-aa3fec540eb5ff87fecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-926f68e15b016ddc1bf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-6900000000-53b966254d033e195810View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue Locations
  • Testes
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010971
KNApSAcK IDC00000613
Chemspider ID4444166
KEGG Compound IDC02646
BioCyc IDNot Available
BiGG ID2299830
Wikipedia LinkParacoumaryl_alcohol
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
4-Coumaryl alcohol → {[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]oxy}sulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Coumaryl alcohol → 3,4,5-trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]phenoxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-Coumaryl alcohol → {4-[(1E)-3-hydroxyprop-1-en-1-yl]phenyl}oxidanesulfonic aciddetails