NAV

3,4-Dihydroxycinnamic Acid

Identification

Generic Name
3,4-Dihydroxycinnamic Acid
DrugBank Accession Number
DB01880
Background

Not Available

Type
Small Molecule
Groups
Experimental, Investigational
Structure
3D
Similar Structures
Weight
Average: 180.1574
Monoisotopic: 180.042258744
Chemical Formula
C9H8O4
Synonyms
Not Available
External IDs
  • NSC-57197
  • NSC-623438
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHistidine ammonia-lyaseNot AvailableRhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158)
UMacrophage migration inhibitory factorNot AvailableHumans
UPhotoactive yellow proteinNot AvailableHalorhodospira halophila
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
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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.
Not Available
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 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
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Catechol / Cinnamic acid / Coumaric acid or derivatives
show 9 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
caffeic acid (CHEBI:16433) / Caffeate derivatives (C01197)
Affected organisms
Not Available

Chemical Identifiers

UNII
U2S3A33KVM
CAS number
331-39-5
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

References

General References
Not Available
Human Metabolome Database
HMDB0003501
KEGG Compound
C01481
PubChem Compound
689043
PubChem Substance
46504491
ChemSpider
600426
BindingDB
4375
ChEBI
16433
ChEMBL
CHEMBL145
ZINC
ZINC000000058172
Therapeutic Targets Database
DNC000378
PDBe Ligand
DHC
PDB Entries
1kou / 2o7d / 3hof / 3s2z / 4eyq / 4fb4 / 4n0s / 4yu7 / 5vfj / 6awu …
show 4 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)3.45Chemaxon
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-MSsplash10-001i-1900000000-6a963e50b910f05b6825
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
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSsplash10-03di-0900000000-f31bbdf32d6b72a381e7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-6a5483f96220bd3dd64d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-741b0dfa9f2bc2cf9ac0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-a3a36ea63a8d065cd267
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-0900000000-fd59e911f9d6c6850b29
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00or-9500000000-24ebe2409e831aaa15f7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-7900000000-7d813624e9b564c812e6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.6487277
predicted
DarkChem Lite v0.1.0
[M-H]-147.7972277
predicted
DarkChem Lite v0.1.0
[M-H]-139.71458
predicted
DeepCCS 1.0 (2019)
[M+H]+149.3959277
predicted
DarkChem Lite v0.1.0
[M+H]+148.9349277
predicted
DarkChem Lite v0.1.0
[M+H]+142.11014
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.5053277
predicted
DarkChem Lite v0.1.0
[M+Na]+148.5861277
predicted
DarkChem Lite v0.1.0
[M+Na]+148.02907
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Histidine ammonia-lyase
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. [Article]
Details2. Macrophage migration inhibitory factor
Kind
Protein
Organism
Humans
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. [Article]
Details3. Photoactive yellow protein
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52