Identification
- Generic Name
- p-Coumaric acid
- DrugBank Accession Number
- DB04066
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for p-Coumaric acid (DB04066)
- Weight
- Average: 164.158
Monoisotopic: 164.047344122 - Chemical Formula
- C9H8O3
- Synonyms
- (2E)-3-(4-hydroxyphenyl)acrylic acid
- (E)-3-(4-hydroxyphenyl)-2-propenoic acid
- (E)-p-coumaric acid
- (E)-p-hydroxycinnamic acid
- 4-coumaric acid
- 4-Hydroxycinnamic acid
- 4'-hydroxycinnamic acid
- naringeninic acid
- p-Coumaric acid
- para-Coumaric Acid
- trans-4-coumaric acid
- trans-4-hydroxycinnamic acid
- trans-p-coumaric acid
- trans-p-coumarinic acid
- trans-p-Hydroxycinnamate
- trans-p-hydroxycinnamic acid
- External IDs
- NSC-59260
- NSC-674321
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UProstaglandin reductase 1 Not Available Humans UHistidine ammonia-lyase Not Available Rhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158) UPhotoactive yellow protein Not Available Halorhodospira halophila UPPH Not Available Rhodospirillum centenum - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with p-Coumaric acid. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with p-Coumaric acid. Acetaminophen The metabolism of p-Coumaric acid can be increased when combined with Acetaminophen. Acetazolamide The metabolism of p-Coumaric acid can be increased when combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with p-Coumaric acid. - Food Interactions
- Not Available
Categories
- Drug Categories
- Acids, Carbocyclic
- Adrenal Cortex Hormones
- Anti-Infective Agents
- Antioxidants
- Biological Factors
- Cinnamates
- Compounds used in a research, industrial, or household setting
- Contraceptive Agents, Male
- Free Radical Scavengers
- Hormonal Contraceptives for Systemic Use
- Protective Agents
- Reproductive Control Agents
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cinnamic acid / Coumaric acid / Coumaric acid or derivatives / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- 4-coumaric acid (CHEBI:32374) / Paracoumaryl alcohol derivatives (C00811)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- IBS9D1EU3J
- CAS number
- 501-98-4
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0002035
- KEGG Compound
- C00811
- PubChem Compound
- 637542
- PubChem Substance
- 46508796
- ChemSpider
- 553148
- BindingDB
- 4374
- 1485787
- ChEBI
- 32374
- ChEMBL
- CHEMBL66879
- ZINC
- ZINC000000039811
- PDBe Ligand
- HC4
- Wikipedia
- P-Coumaric_acid
- PDB Entries
- 1d7e / 1f98 / 1f9i / 1gsv / 1gsw / 1gsx / 1mzu / 1nwz / 1odv / 1ot6 … show 93 more
Clinical Trials
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
Property Value Source Water Solubility 1.02 mg/mL ALOGPS logP 1.74 ALOGPS logP 1.83 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 3.81 Chemaxon pKa (Strongest Basic) -6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.53 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 45.04 m3·mol-1 Chemaxon Polarizability 16.43 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9938 Blood Brain Barrier + 0.5237 Caco-2 permeable + 0.8839 P-glycoprotein substrate Non-substrate 0.7196 P-glycoprotein inhibitor I Non-inhibitor 0.9812 P-glycoprotein inhibitor II Non-inhibitor 0.9899 Renal organic cation transporter Non-inhibitor 0.9091 CYP450 2C9 substrate Non-substrate 0.7889 CYP450 2D6 substrate Non-substrate 0.9364 CYP450 3A4 substrate Non-substrate 0.746 CYP450 1A2 substrate Non-inhibitor 0.9458 CYP450 2C9 inhibitor Non-inhibitor 0.9364 CYP450 2D6 inhibitor Non-inhibitor 0.9766 CYP450 2C19 inhibitor Non-inhibitor 0.9116 CYP450 3A4 inhibitor Non-inhibitor 0.8693 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8913 Ames test Non AMES toxic 0.9521 Carcinogenicity Non-carcinogens 0.8248 Biodegradation Ready biodegradable 0.7156 Rat acute toxicity 1.3698 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9502 hERG inhibition (predictor II) Non-inhibitor 0.9796
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 142.5503411 predictedDarkChem Lite v0.1.0 [M-H]- 143.5020349 predictedDarkChem Standard v0.1.0 [M-H]- 142.4915411 predictedDarkChem Lite v0.1.0 [M-H]- 132.54143 predictedDeepCCS 1.0 (2019) [M+H]+ 145.8870411 predictedDarkChem Lite v0.1.0 [M+H]+ 148.1257411 predictedDarkChem Lite v0.1.0 [M+H]+ 145.1943411 predictedDarkChem Lite v0.1.0 [M+H]+ 134.937 predictedDeepCCS 1.0 (2019) [M+Na]+ 143.1890411 predictedDarkChem Lite v0.1.0 [M+Na]+ 143.4536411 predictedDarkChem Lite v0.1.0 [M+Na]+ 143.6507411 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.19545 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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. [Article]
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52