Identification

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Name
trans-2-hydroxycinnamic acid
Accession Number
DB01650  (EXPT00123)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
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
Categories
UNII
23AU5FZB9C
CAS number
614-60-8
Weight
Average: 164.158
Monoisotopic: 164.047344122
Chemical Formula
C9H8O3
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMajor NAD(P)H-flavin oxidoreductaseNot AvailableVibrio 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
Toxicity
Not Available
Affected organisms
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.
DrugInteraction
AcyclovirThe excretion of Acyclovir can be decreased when combined with trans-2-hydroxycinnamic acid.
AllopurinolThe excretion of Allopurinol can be decreased when combined with trans-2-hydroxycinnamic acid.
AlprostadilThe excretion of Alprostadil can be decreased when combined with trans-2-hydroxycinnamic acid.
Aminohippuric acidThe excretion of Aminohippuric acid can be decreased when combined with trans-2-hydroxycinnamic acid.
AvibactamThe excretion of Avibactam can be decreased when combined with trans-2-hydroxycinnamic acid.
BaricitinibThe excretion of Baricitinib can be decreased when combined with trans-2-hydroxycinnamic acid.
BenzylpenicillinThe excretion of Benzylpenicillin can be decreased when combined with trans-2-hydroxycinnamic acid.
BumetanideThe excretion of Bumetanide can be decreased when combined with trans-2-hydroxycinnamic acid.
CaptoprilThe excretion of Captopril can be decreased when combined with trans-2-hydroxycinnamic acid.
CefacetrileThe excretion of Cefacetrile can be decreased when combined with trans-2-hydroxycinnamic acid.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

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
HET
2HC
PDB Entries
1v5z / 5bnl

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
PropertyValueSource
melting point (°C)217 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.15 mg/mLALOGPS
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
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
Polarizability16.11 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9933
Blood Brain Barrier+0.5915
Caco-2 permeable+0.9073
P-glycoprotein substrateNon-substrate0.7146
P-glycoprotein inhibitor INon-inhibitor0.9711
P-glycoprotein inhibitor IINon-inhibitor0.9922
Renal organic cation transporterNon-inhibitor0.912
CYP450 2C9 substrateNon-substrate0.7759
CYP450 2D6 substrateNon-substrate0.918
CYP450 3A4 substrateNon-substrate0.7423
CYP450 1A2 substrateNon-inhibitor0.9405
CYP450 2C9 inhibitorNon-inhibitor0.8044
CYP450 2D6 inhibitorNon-inhibitor0.9532
CYP450 2C19 inhibitorNon-inhibitor0.7183
CYP450 3A4 inhibitorNon-inhibitor0.9062
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8008
Ames testNon AMES toxic0.9217
CarcinogenicityNon-carcinogens0.8663
BiodegradationReady biodegradable0.6546
Rat acute toxicity1.6615 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9513
hERG inhibition (predictor II)Non-inhibitor0.9712
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) (2 TMS)GC-MSsplash10-0002-0910000000-9e0bdbf6d6389288e318
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00dj-9710000000-829ded288e3ec8312160
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00dj-9710000000-8fb7bb39d916f7402980
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0296-2941000000-b85ebef8eb8c276f220f
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-014i-9800000000-3650ee76a1293cba7523
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0910000000-9e0bdbf6d6389288e318
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dj-9710000000-829ded288e3ec8312160
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dj-9710000000-8fb7bb39d916f7402980
GC-MS Spectrum - GC-MSGC-MSsplash10-0296-2941000000-b85ebef8eb8c276f220f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0910000000-c783499d6f33717b71ca
Mass Spectrum (Electron Ionization)MSsplash10-014j-8900000000-8e96a9ec1b9d035d3edb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-03di-0900000000-9e4823d321cfe6f5e5a4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-014i-0900000000-efd5de4e7fe4032816f6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-014i-0900000000-44e81c2c735a93efc7d7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-014l-7900000000-977a2bb08508d16be531
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0fdn-4900000000-dcfe2b032cf6bbee16b3
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-03di-0900000000-adbaf7b04487b18191e0
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
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-d368e3c354c7b05a949f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-efd5de4e7fe4032816f6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-44e81c2c735a93efc7d7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014l-7900000000-a641b2c2528f829e8ac1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03di-0900000000-adbaf7b04487b18191e0
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0900000000-2ca69c9285dedaa2f424
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0900000000-55078e8ec591840fb594
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fdn-4900000000-95f5386456c1c353a111
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-4-unsubstituted benzenoids / 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-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Benzenoid
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, 2-coumaric acid (CHEBI:18125) / Monolignols (C01772)

Targets

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
  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]

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
  1. 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. [PubMed:11967025]

Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 05:55