NAV

Prephenic acid

Identification

Generic Name
Prephenic acid
DrugBank Accession Number
DB08427
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 226.1828
Monoisotopic: 226.047738052
Chemical Formula
C10H10O6
Synonyms
  • (1s,4s)-prephenic acid
  • cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid
  • cis-prephenic acid
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Pharmacology

Indication

Not Available

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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

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 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
Alcohol / Aliphatic homomonocyclic compound / Alpha-hydroxy ketone / Alpha-keto acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Gamma-keto acid / Hydrocarbon derivative
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
prephenic acid (CHEBI:84387)
Affected organisms
Not Available

Chemical Identifiers

UNII
Z66B98Z97I
CAS number
126-49-8
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

References

General References
Not Available
KEGG Compound
C00254
PubChem Compound
1028
PubChem Substance
99444898
ChemSpider
16735981
ChEBI
84387
ZINC
ZINC000100036740
PDBe Ligand
PRE
Wikipedia
Prephenic_acid
PDB Entries
1com / 3zp7 / 5j6f / 6al9

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility36.0 mg/mLALOGPS
logP-0.31ALOGPS
logP0.061Chemaxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.86Chemaxon
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-MSsplash10-0006-9610000000-b3ced3fa2b10936d8535
GC-MS Spectrum - EI-BGC-MSsplash10-014u-6920000000-ef53f0db72ce3c5aa0c4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0920000000-8c3d631a7c6ce8920e2c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bti-4910000000-11df16f72a2ff7927b97
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1980000000-b18b07040dd84199fae9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-2082db1aa05788d90958
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-4900000000-cf6cf0934bfd2fb124b7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001u-1900000000-e10901430d6ca85e23f6
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]-155.3065853
predicted
DarkChem Lite v0.1.0
[M-H]-145.30647
predicted
DeepCCS 1.0 (2019)
[M+H]+155.1875853
predicted
DarkChem Lite v0.1.0
[M+H]+147.70209
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.2355853
predicted
DarkChem Lite v0.1.0
[M+Na]+153.61461
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Chorismate mutase AroH
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. [Article]

Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52