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Identification
NamePara-Coumaric Acid
Accession NumberDB04066  (EXPT01706)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 164.158
Monoisotopic: 164.047344122
Chemical FormulaC9H8O3
InChI KeyInChIKey=NGSWKAQJJWESNS-ZZXKWVIFSA-N
InChI
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
IUPAC Name
(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
SMILES
OC(=O)\C=C\C1=CC=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Coumaric acid
  • Cinnamic acid
  • Phenylpropene
  • Styrene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9938
Blood Brain Barrier+0.5237
Caco-2 permeable+0.8839
P-glycoprotein substrateNon-substrate0.7196
P-glycoprotein inhibitor INon-inhibitor0.9812
P-glycoprotein inhibitor IINon-inhibitor0.9899
Renal organic cation transporterNon-inhibitor0.9091
CYP450 2C9 substrateNon-substrate0.7889
CYP450 2D6 substrateNon-substrate0.9364
CYP450 3A4 substrateNon-substrate0.746
CYP450 1A2 substrateNon-inhibitor0.9458
CYP450 2C9 inhibitorNon-inhibitor0.9364
CYP450 2D6 inhibitorNon-inhibitor0.9766
CYP450 2C19 inhibitorNon-inhibitor0.9116
CYP450 3A4 inhibitorNon-inhibitor0.8693
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8913
Ames testNon AMES toxic0.9521
CarcinogenicityNon-carcinogens0.8248
BiodegradationReady biodegradable0.7156
Rat acute toxicity1.3698 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9502
hERG inhibition (predictor II)Non-inhibitor0.9796
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.02 mg/mLALOGPS
logP1.74ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m3·mol-1ChemAxon
Polarizability16.43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-5zy6000000-e7648e85764a445a919cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-cuz7000000-a5712bbe8401ef499b5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-wz00000000-3bb023f80c1f54a16adcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-2z00000000-b58aab08954c973df04eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-3z00000000-3ddb41572ba36a950e37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-3z00000000-ccac7f071084bc660095View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-fz00000000-5dc8af06da0120779cffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-zm00000000-9187edc4498ab4345e5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-cz00000000-1118928776a5a6e213dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-1z00000000-3d831c6acd9d3188de2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0z00000000-fbb6439b7d012045f3a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0z00000000-9e18d43a8d86f9b9e72bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-pz00000000-348f5c7c030570e0612fView in MoNA
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Halorhodospira halophila
Pharmacological action
unknown
General Function:
Photoreceptor activity
Specific Function:
Photoactive blue light protein. Probably functions as a photoreceptor for a negative phototaxis response.
Gene Name:
pyp
Uniprot ID:
P16113
Molecular Weight:
13873.54 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 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Rhodospirillum centenum
Pharmacological action
unknown
General Function:
Photoreceptor activity
Specific Function:
Not Available
Gene Name:
pph
Uniprot ID:
Q9X2W8
Molecular Weight:
95972.565 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Functions as 15-oxo-prostaglandin 13-reductase and acts on 15-oxo-PGE1, 15-oxo-PGE2 and 15-oxo-PGE2-alpha. Has no activity towards PGE1, PGE2 and PGE2-alpha (By similarity). Catalyzes the conversion of leukotriene B4 into its biologically less active metabolite, 12-oxo-leukotriene B4. This is an initial and key step of metabolic inactivation of leukotriene B4.
Gene Name:
PTGR1
Uniprot ID:
Q14914
Molecular Weight:
35869.64 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Rhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158)
Pharmacological action
unknown
General Function:
Tyrosine ammonia-lyase activity
Specific Function:
Catalyzes the non-oxidative deamination of L-tyrosine. Has very low phenylalanine ammonia-lyase activity (in vitro).
Gene Name:
hutH
Uniprot ID:
Q3IWB0
Molecular Weight:
54913.16 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23