3-(4-HYDROXY-PHENYL)PYRUVIC ACID

Identification

Name
3-(4-HYDROXY-PHENYL)PYRUVIC ACID
Accession Number
DB07718
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-100738 / NSC-666757
Categories
Not Available
UNII
0YP1694WNQ
CAS number
Not Available
Weight
Average: 180.1574
Monoisotopic: 180.042258744
Chemical Formula
C9H8O4
InChI Key
KKADPXVIOXHVKN-UHFFFAOYSA-N
InChI
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
IUPAC Name
3-(4-hydroxyphenyl)-2-oxopropanoic acid
SMILES
OC(=O)C(=O)CC1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProthrombinNot AvailableHuman
UMacrophage migration inhibitory factorNot AvailableHuman
UPrephenate dehydrogenaseNot AvailableAquifex aeolicus (strain VF5)
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
PathwayCategory
PhenylketonuriaDisease
Tyrosinemia Type IDisease
Disulfiram Action PathwayDrug action
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)Disease
Tyrosinemia Type 3 (TYRO3)Disease
Tyrosine MetabolismMetabolic
Tyrosinemia, transient, of the newbornDisease
Phenylalanine and Tyrosine MetabolismMetabolic
AlkaptonuriaDisease
HawkinsinuriaDisease
Dopamine beta-hydroxylase deficiencyDisease
Monoamine oxidase-a deficiency (MAO-A)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00707
KEGG Compound
C01179
PubChem Compound
979
PubChem Substance
99444189
ChemSpider
954
ChEBI
15999
ChEMBL
CHEMBL607712
HET
ENO
PDB Entries
1ca7 / 3gac / 3ggo / 3ijj / 3tx6 / 3uk0 / 3ukj / 4eyq / 4jb0 / 4kig

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.49 mg/mLALOGPS
logP1.12ALOGPS
logP1.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.69 m3·mol-1ChemAxon
Polarizability16.75 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8829
Blood Brain Barrier+0.6663
Caco-2 permeable-0.6945
P-glycoprotein substrateNon-substrate0.7002
P-glycoprotein inhibitor INon-inhibitor0.961
P-glycoprotein inhibitor IINon-inhibitor0.9607
Renal organic cation transporterNon-inhibitor0.9201
CYP450 2C9 substrateNon-substrate0.8473
CYP450 2D6 substrateNon-substrate0.9196
CYP450 3A4 substrateNon-substrate0.7244
CYP450 1A2 substrateNon-inhibitor0.9836
CYP450 2C9 inhibitorNon-inhibitor0.9768
CYP450 2D6 inhibitorNon-inhibitor0.9701
CYP450 2C19 inhibitorNon-inhibitor0.9761
CYP450 3A4 inhibitorNon-inhibitor0.965
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9844
Ames testNon AMES toxic0.896
CarcinogenicityNon-carcinogens0.9065
BiodegradationReady biodegradable0.8661
Rat acute toxicity1.7101 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9655
hERG inhibition (predictor II)Non-inhibitor0.9699
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)GC-MSsplash10-002f-1920000000-75b07d9c09371340939f
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00xr-9340000000-087aad2497b3493d27c0
GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)GC-MSsplash10-002o-5910000000-fd1e55c84c79bfeca559
GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)GC-MSsplash10-002f-1941000000-2b4c87544657895fcaf6
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-014i-3492100000-483bdcea11d60fe4d306
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-014i-6791000000-ddc0a3b695cd1d0769f2
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-002f-1951000000-ecd071a64b26ca77684c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-002f-1920000000-75b07d9c09371340939f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00xr-9340000000-087aad2497b3493d27c0
GC-MS Spectrum - GC-MSGC-MSsplash10-002o-5910000000-fd1e55c84c79bfeca559
GC-MS Spectrum - GC-MSGC-MSsplash10-002f-1941000000-2b4c87544657895fcaf6
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-3492100000-483bdcea11d60fe4d306
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-6791000000-ddc0a3b695cd1d0769f2
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-2920000000-469469dfaad745fa78e8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-002o-2910000000-4f336335a2366e7dd6db
Mass Spectrum (Electron Ionization)MSsplash10-0a59-5900000000-6c003e26816579df31ca
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0a4i-0900000000-12033042c41b550bed42
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0a4i-0900000000-6e8a3701c6d254cc824d
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0560-1900000000-8082c68e259d24234d05
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-2416d7f64101b9473cbb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0a4i-2900000000-b4c21b3d9751b9e56d67
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0005-9400000000-708e258e692a0abfbc92
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0002-9100000000-7d75e23ae6944c1e9c6d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-001m-9000000000-fb80dcbab23323a042af
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-08gr-0900000000-be3cb913118057f499d1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-06rj-0900000000-6bebea0fda2ef3a2263b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-6900000000-ede11b81a97e891c66e3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-2584f872c980915c1739
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01s9-1900000000-249c71cfa9cefe2a8020
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-3900000000-66991d861a91be9b9286
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-2416d7f64101b9473cbb
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-2900000000-ad1f1fabdf6b1579fff7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0005-9400000000-708e258e692a0abfbc92
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9100000000-7d75e23ae6944c1e9c6d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001m-9000000000-fb80dcbab23323a042af
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-1900000000-76ae33b45e4348d50b07
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpyruvic acid derivatives. These are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpyruvic acid derivatives
Direct Parent
Phenylpyruvic acid derivatives
Alternative Parents
Phenylpropanoic acids / 1-hydroxy-2-unsubstituted benzenoids / Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Phenylpyruvate / 3-phenylpropanoic-acid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Alpha-keto acid / Keto acid / Alpha-hydroxy ketone / Ketone / Carboxylic acid derivative / Carboxylic acid
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, oxo carboxylic acid (CHEBI:15999)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Thrombospondin receptor activity
Specific Function
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostas...
Gene Name
F2
Uniprot ID
P00734
Uniprot Name
Prothrombin
Molecular Weight
70036.295 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]
Kind
Protein
Organism
Aquifex aeolicus (strain VF5)
Pharmacological action
Unknown
General Function
Prephenate dehydrogenase activity
Specific Function
Not Available
Gene Name
tyrA
Uniprot ID
O67636
Uniprot Name
Prephenate dehydrogenase
Molecular Weight
34849.26 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 September 15, 2010 15:25 / Updated on November 09, 2017 04:19