Identification
- Generic Name
- trans-2-hydroxycinnamic acid
- DrugBank Accession Number
- DB01650
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for trans-2-hydroxycinnamic acid (DB01650)
- Weight
- Average: 164.158
Monoisotopic: 164.047344122 - Chemical Formula
- C9H8O3
- Synonyms
- (2E)-3-(2-hydroxyphenyl)-2-propenoic acid
- (2E)-3-(2-hydroxyphenyl)prop-2-enoic acid
- (E)-3-(2-Hydroxyphenyl)-2-propenoic acid
- (E)-o-hydroxycinnamic acid
- 2-Coumarate
- 2-Coumaric acid
- 2-Hydroxycinnamate
- o-Coumaric acid
- o-hydroxy-trans-cinnamic acid
- trans-2-Hydroxycinnamate
- trans-o-hydroxycinnamic acid
- External IDs
- NSC-32952
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 UMajor NAD(P)H-flavin oxidoreductase Not Available Vibrio fischeri - 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 softwareAcamprosate The excretion of Acamprosate can be decreased when combined with trans-2-hydroxycinnamic acid. Acyclovir The excretion of Acyclovir can be decreased when combined with trans-2-hydroxycinnamic acid. Allopurinol The excretion of Allopurinol can be decreased when combined with trans-2-hydroxycinnamic acid. Aminohippuric acid The excretion of Aminohippuric acid can be decreased when combined with trans-2-hydroxycinnamic acid. Avibactam The excretion of Avibactam can be decreased when combined with trans-2-hydroxycinnamic acid. - Food Interactions
- Not Available
Categories
- Drug Categories
- 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-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cinnamic acid / Coumaric acid / Coumaric acid or derivatives
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols, 2-coumaric acid (CHEBI:18125) / Monolignols (C01772)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 23AU5FZB9C
- CAS number
- 614-60-8
- InChI Key
- PMOWTIHVNWZYFI-AATRIKPKSA-N
- InChI
- InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+
- IUPAC Name
- (2E)-3-(2-hydroxyphenyl)prop-2-enoic acid
- SMILES
- OC(=O)\C=C\C1=CC=CC=C1O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0002641
- KEGG Compound
- C01772
- PubChem Compound
- 637540
- PubChem Substance
- 46505688
- ChemSpider
- 553146
- BindingDB
- 50146462
- ChEBI
- 18125
- ChEMBL
- CHEMBL52564
- ZINC
- ZINC000000895911
- PDBe Ligand
- 2HC
- PDB Entries
- 1v5z / 5bnl
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 217 dec °C PhysProp - Predicted Properties
Property Value Source Water Solubility 1.15 mg/mL ALOGPS logP 1.9 ALOGPS logP 1.83 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 3.85 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 16.11 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 + 0.9933 Blood Brain Barrier + 0.5915 Caco-2 permeable + 0.9073 P-glycoprotein substrate Non-substrate 0.7146 P-glycoprotein inhibitor I Non-inhibitor 0.9711 P-glycoprotein inhibitor II Non-inhibitor 0.9922 Renal organic cation transporter Non-inhibitor 0.912 CYP450 2C9 substrate Non-substrate 0.7759 CYP450 2D6 substrate Non-substrate 0.918 CYP450 3A4 substrate Non-substrate 0.7423 CYP450 1A2 substrate Non-inhibitor 0.9405 CYP450 2C9 inhibitor Non-inhibitor 0.8044 CYP450 2D6 inhibitor Non-inhibitor 0.9532 CYP450 2C19 inhibitor Non-inhibitor 0.7183 CYP450 3A4 inhibitor Non-inhibitor 0.9062 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8008 Ames test Non AMES toxic 0.9217 Carcinogenicity Non-carcinogens 0.8663 Biodegradation Ready biodegradable 0.6546 Rat acute toxicity 1.6615 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9513 hERG inhibition (predictor II) Non-inhibitor 0.9712
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.8720411 predictedDarkChem Lite v0.1.0 [M-H]- 137.6134609 predictedDarkChem Standard v0.1.0 [M-H]- 140.4412411 predictedDarkChem Lite v0.1.0 [M-H]- 133.02477 predictedDeepCCS 1.0 (2019) [M+H]+ 142.2866411 predictedDarkChem Lite v0.1.0 [M+H]+ 141.0256411 predictedDarkChem Lite v0.1.0 [M+H]+ 141.3067411 predictedDarkChem Lite v0.1.0 [M+H]+ 135.42033 predictedDeepCCS 1.0 (2019) [M+Na]+ 140.4173411 predictedDarkChem Lite v0.1.0 [M+Na]+ 140.7481411 predictedDarkChem Lite v0.1.0 [M+Na]+ 140.8151411 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.35567 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Vibrio fischeri
- Pharmacological action
- Unknown
- General Function
- Oxidoreductase activity
- Specific Function
- Involved in bioluminescence. It is a good supplier of reduced flavin mononucleotide (FMNH2) to the bioluminescence reaction. Major FMN reductase. It is capable of using both NADH and NADPH as elect...
- Gene Name
- Not Available
- Uniprot ID
- P46072
- Uniprot Name
- Major NAD(P)H-flavin oxidoreductase
- Molecular Weight
- 24720.685 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]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Deguchi T, Ohtsuki S, Otagiri M, Takanaga H, Asaba H, Mori S, Terasaki T: Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney. Kidney Int. 2002 May;61(5):1760-8. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51