3,4-Dihydroxycinnamic Acid

Identification

Name
3,4-Dihydroxycinnamic Acid
Accession Number
DB01880  (EXPT01188)
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-57197 / NSC-623438
Categories
UNII
U2S3A33KVM
CAS number
331-39-5
Weight
Average: 180.1574
Monoisotopic: 180.042258744
Chemical Formula
C9H8O4
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPhotoactive yellow proteinNot AvailableHalorhodospira halophila
UHistidine ammonia-lyaseNot AvailableRhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158)
UMacrophage migration inhibitory factorNot AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB03501
KEGG Compound
C01481
PubChem Compound
689043
PubChem Substance
46504491
ChemSpider
600426
BindingDB
4375
ChEBI
16433
ChEMBL
CHEMBL145
Therapeutic Targets Database
DNC000378
HET
DHC
PDB Entries
1kou / 2o7d / 3hof / 3s2z / 4eyq / 4fb4 / 4n0s / 4yu7

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentImmune Thrombocytopenia1

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)225 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-014i-1593000000-b24e97b50ed1f50252f3
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9800000000-bae43e98e22babcbf5a7
GC-MS Spectrum - EI-BGC-MSsplash10-000i-9600000000-6140146b8e32bda5e3c9
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0593000000-16610dfa8ac4ac67a4c2
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1593000000-b24e97b50ed1f50252f3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0592000000-1bb03bc99be6718d247e
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
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available

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 and derivatives / Cinnamic acids / Styrenes / Catechols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Cinnamic acid / Coumaric acid or derivatives / Hydroxycinnamic acid / Catechol / Styrene / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Benzenoid
show 9 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
caffeic acid (CHEBI:16433) / Caffeate derivatives (C01197)

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
Uniprot Name
Photoactive yellow protein
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
Uniprot Name
Tyrosine ammonia-lyase
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 ma...
Gene Name
MIF
Uniprot ID
P14174
Uniprot Name
Macrophage migration inhibitory factor
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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:06