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Identification
Name3,4-Dihydroxycinnamic Acid
Accession NumberDB01880  (EXPT01188)
Typesmall molecule
Groupsexperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number331-39-5
WeightAverage: 180.1574
Monoisotopic: 180.042258744
Chemical FormulaC9H8O4
InChI KeyInChIKey=QAIPRVGONGVQAS-DUXPYHPUSA-N
InChI
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
IUPAC Name
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
SMILES
OC(=O)\C=C\C1=CC(O)=C(O)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassCinnamic Acids and Derivatives
SubclassCinnamic Acids
Direct parentCinnamic Acids
Alternative parentsHydroxycinnamic Acids; Coumaric Acids and Derivatives; Phenylpropenes; Catechols; Styrenes; Enones; Polyols; Polyamines; Enolates; Enols; Carboxylic Acids
Substituentsphenylpropene; styrene; 1,2-diphenol; phenol derivative; benzene; enone; polyol; enolate; enol; polyamine; carboxylic acid; carboxylic acid derivative
Classification descriptionThis compound belongs to the cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9392
Blood Brain Barrier - 0.6322
Caco-2 permeable + 0.5693
P-glycoprotein substrate Non-substrate 0.6451
P-glycoprotein inhibitor I Non-inhibitor 0.9738
P-glycoprotein inhibitor II Non-inhibitor 0.9935
Renal organic cation transporter Non-inhibitor 0.9387
CYP450 2C9 substrate Non-substrate 0.8014
CYP450 2D6 substrate Non-substrate 0.9136
CYP450 3A4 substrate Non-substrate 0.7046
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9525
CYP450 2C19 substrate Non-inhibitor 0.9367
CYP450 3A4 substrate Non-inhibitor 0.8869
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9007
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.9183
Biodegradation Ready biodegradable 0.8012
Rat acute toxicity 1.4041 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9763
hERG inhibition (predictor II) Non-inhibitor 0.9548
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point225 dec °CPhysProp
logP1.15SANGSTER (1993)
pKa4.62 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
water solubility1.61e+00 g/lALOGPS
logP1.67ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (strongest acidic)3.64ChemAxon
pKa (strongest basic)-6.3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area77.76ChemAxon
rotatable bond count2ChemAxon
refractivity47.02ChemAxon
polarizability17.34ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC01481
PubChem Compound689043
PubChem Substance46504491
ChemSpider600426
ChEBI17395
ChEMBL
Therapeutic Targets DatabaseDNC000378
HETDHC
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Photoactive yellow protein

Kind: protein

Organism: Halorhodospira halophila

Pharmacological action: unknown

Components

Name UniProt ID Details
Photoactive yellow protein P16113 Details

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
  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
  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

2. Histidine ammonia-lyase

Kind: protein

Organism: Rhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158)

Pharmacological action: unknown

Components

Name UniProt ID Details
Histidine ammonia-lyase Q3IWB0 Details

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

3. Macrophage migration inhibitory factor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Macrophage migration inhibitory factor P14174 Details

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

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:16