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Identification
Name3,4-Dihydroxycinnamic Acid
Accession NumberDB01880  (EXPT01188)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIU2S3A33KVM
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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Cinnamic acid
  • Phenylpropene
  • Styrene
  • 1,2-diphenol
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9392
Blood Brain Barrier-0.6322
Caco-2 permeable+0.5693
P-glycoprotein substrateNon-substrate0.6451
P-glycoprotein inhibitor INon-inhibitor0.9738
P-glycoprotein inhibitor IINon-inhibitor0.9935
Renal organic cation transporterNon-inhibitor0.9387
CYP450 2C9 substrateNon-substrate0.8014
CYP450 2D6 substrateNon-substrate0.9136
CYP450 3A4 substrateNon-substrate0.7046
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9525
CYP450 2C19 inhibitorNon-inhibitor0.9367
CYP450 3A4 inhibitorNon-inhibitor0.8869
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9007
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9183
BiodegradationReady biodegradable0.8012
Rat acute toxicity1.4041 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9763
hERG inhibition (predictor II)Non-inhibitor0.9548
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 Solubility1.61 mg/mLALOGPS
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 Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m3·mol-1ChemAxon
Polarizability17.34 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1593000000-b24e97b50ed1f50252f3View in MoNA
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
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
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
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Receptor binding
Specific Function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate...
Gene Name:
MIF
Uniprot ID:
P14174
Molecular Weight:
12476.19 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 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:16