PREPHENIC ACID

Identification

Name
PREPHENIC ACID
Accession Number
DB08427
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Z66B98Z97I
CAS number
Not Available
Weight
Average: 226.1828
Monoisotopic: 226.047738052
Chemical Formula
C10H10O6
InChI Key
FPWMCUPFBRFMLH-XGAOUMNUSA-N
InChI
InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+
IUPAC Name
(1s,4s)-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
SMILES
[H][C@]1(O)C=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UChorismate mutase AroHNot AvailableBacillus subtilis (strain 168)
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
KEGG Compound
C00254
PubChem Compound
1028
PubChem Substance
99444898
ChemSpider
16735981
ChEBI
84387
HET
PRE
PDB Entries
1com / 3zp7 / 5j6f / 6al9

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 Solubility36.0 mg/mLALOGPS
logP-0.31ALOGPS
logP0.061ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.55 m3·mol-1ChemAxon
Polarizability19.73 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8824
Blood Brain Barrier+0.8557
Caco-2 permeable-0.6835
P-glycoprotein substrateNon-substrate0.6661
P-glycoprotein inhibitor INon-inhibitor0.9217
P-glycoprotein inhibitor IINon-inhibitor0.9515
Renal organic cation transporterNon-inhibitor0.9185
CYP450 2C9 substrateNon-substrate0.848
CYP450 2D6 substrateNon-substrate0.9213
CYP450 3A4 substrateNon-substrate0.6495
CYP450 1A2 substrateNon-inhibitor0.9847
CYP450 2C9 inhibitorNon-inhibitor0.966
CYP450 2D6 inhibitorNon-inhibitor0.9601
CYP450 2C19 inhibitorNon-inhibitor0.968
CYP450 3A4 inhibitorNon-inhibitor0.909
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.989
Ames testNon AMES toxic0.9128
CarcinogenicityNon-carcinogens0.8932
BiodegradationNot ready biodegradable0.7547
Rat acute toxicity1.6802 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9888
hERG inhibition (predictor II)Non-inhibitor0.9778
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-014u-6920000000-ef53f0db72ce3c5aa0c4
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Keto acids and derivatives
Sub Class
Gamma-keto acids and derivatives
Direct Parent
Gamma-keto acids and derivatives
Alternative Parents
Dicarboxylic acids and derivatives / Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Secondary alcohols / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Gamma-keto acid / Dicarboxylic acid or derivatives / Alpha-keto acid / Alpha-hydroxy ketone / Secondary alcohol / Ketone / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
prephenic acid (CHEBI:84387)

Targets

Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Chorismate mutase activity
Specific Function
Catalyzes the Claisen rearrangement of chorismate to prephenate. Probably involved in the aromatic amino acid biosynthesis.
Gene Name
aroH
Uniprot ID
P19080
Uniprot Name
Chorismate mutase AroH
Molecular Weight
14516.91 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 15:31 / Updated on November 02, 2018 06:49