para-Coumaric Acid

Identification

Name
para-Coumaric Acid
Accession Number
DB04066  (EXPT01706)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 4-coumaric acid
  • p-Coumaric acid
External IDs
NSC-59260 / NSC-674321
Categories
UNII
IBS9D1EU3J
CAS number
Not Available
Weight
Average: 164.158
Monoisotopic: 164.047344122
Chemical Formula
C9H8O3
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPhotoactive yellow proteinNot AvailableHalorhodospira halophila
UPPHNot AvailableRhodospirillum centenum
UProstaglandin reductase 1Not AvailableHuman
UHistidine ammonia-lyaseNot AvailableRhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158)
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB02035
KEGG Compound
C00811
PubChem Compound
637542
PubChem Substance
46508796
ChemSpider
553148
BindingDB
4374
ChEBI
32374
ChEMBL
CHEMBL66879
HET
HC4
PDB Entries
1d7e / 1f98 / 1f9i / 1gsv / 1gsw / 1gsx / 1mzu / 1nwz / 1odv / 1ot6
show 67 more

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
Not 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014m-1981000000-e7648e85764a445a919c
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-066v-3791000000-a5712bbe8401ef499b5a
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03di-8900000000-3bb023f80c1f54a16adc
GC-MS Spectrum - EI-BGC-MSsplash10-03xr-5900000000-a364c62c9122c0fbe6de
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014m-1981000000-e7648e85764a445a919c
GC-MS Spectrum - GC-MSGC-MSsplash10-066v-3791000000-a5712bbe8401ef499b5a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014m-1891000000-d8804981d3918cac534d
Mass Spectrum (Electron Ionization)MSsplash10-03xr-6900000000-348f5c7c030570e0612f
MS/MS Spectrum - EI-B (HITACHI M-52) , PositiveLC-MS/MSsplash10-03di-8900000000-3bb023f80c1f54a16adc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-03di-0900000000-b58aab08954c973df04e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-014i-0900000000-3ddb41572ba36a950e37
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-014i-0900000000-ccac7f071084bc660095
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-014i-3900000000-5dc8af06da0120779cff
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00kf-9500000000-9187edc4498ab4345e5a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00kb-3900000000-1118928776a5a6e213db
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-014i-0900000000-3d831c6acd9d3188de2f
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-03di-0900000000-fbb6439b7d012045f3a8
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, NegativeLC-MS/MSsplash10-0002-0900000000-9e18d43a8d86f9b9e72b
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
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-b58aab08954c973df04e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-3ddb41572ba36a950e37
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-ccac7f071084bc660095
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-3900000000-5dc8af06da0120779cff
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kf-9500000000-9187edc4498ab4345e5a
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-3d831c6acd9d3188de2f
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03di-0900000000-fbb6439b7d012045f3a8
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0002-0900000000-9e18d43a8d86f9b9e72b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kb-3900000000-1118928776a5a6e213db
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014j-0900000000-9d72cbee7a67e7f3df3a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00kb-4964433233-843b27271ab3bf809f7d
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamic acids and derivatives
Sub Class
Hydroxycinnamic acids and derivatives
Direct Parent
Hydroxycinnamic acids
Alternative Parents
Coumaric acids / Cinnamic acids / Styrenes / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Cinnamic acid / Coumaric acid / Coumaric acid or derivatives / Hydroxycinnamic acid / Styrene / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Benzenoid / Carboxylic acid derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
4-coumaric acid (CHEBI:32374) / Paracoumaryl alcohol derivatives (C00811)

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
Uniprot Name
Photoactive yellow protein
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
Uniprot Name
PPH
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 conversio...
Gene Name
PTGR1
Uniprot ID
Q14914
Uniprot Name
Prostaglandin reductase 1
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
Uniprot Name
Tyrosine ammonia-lyase
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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:36