Isocitric Acid

Identification

Name
Isocitric Acid
Accession Number
DB01727  (EXPT01834)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
9RW6G5D4MQ
CAS number
320-77-4
Weight
Average: 192.1235
Monoisotopic: 192.02700261
Chemical Formula
C6H8O7
InChI Key
ODBLHEXUDAPZAU-OKKQSCSOSA-N
InChI
InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4-/m0/s1
IUPAC Name
(1S,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid
SMILES
O[C@@H]([C@H](CC(O)=O)C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UIsocitrate dehydrogenase [NADP]Not AvailableEscherichia coli (strain K12)
UIsocitrate dehydrogenase [NADP]Not AvailableAzotobacter vinelandii
UAconitate hydratase, mitochondrialNot AvailableHuman
UIsocitrate dehydrogenase [NADP], mitochondrialNot AvailableHuman
UIsocitrate dehydrogenase [NADP] cytoplasmicNot AvailableHuman
UMethylisocitrate lyaseNot AvailableEscherichia coli (strain K12)
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

Synthesis Reference

Eddie N. Gutierrez, Vincent Lamberti, "Process for preparing isocitric acid, alloisocitric acid and lactones thereof." U.S. Patent US4022803, issued May 10, 1977.

US4022803
General References
Not Available
External Links
KEGG Compound
C04617
PubChem Compound
447805
PubChem Substance
46506619
ChemSpider
394789
ChEBI
160
HET
N81
PDB Entries
5fy8

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 Solubility52.5 mg/mLALOGPS
logP-0.35ALOGPS
logP-1.4ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.72 m3·mol-1ChemAxon
Polarizability15.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6961
Blood Brain Barrier+0.7646
Caco-2 permeable-0.8985
P-glycoprotein substrateNon-substrate0.68
P-glycoprotein inhibitor INon-inhibitor0.9716
P-glycoprotein inhibitor IINon-inhibitor0.9632
Renal organic cation transporterNon-inhibitor0.9625
CYP450 2C9 substrateNon-substrate0.8608
CYP450 2D6 substrateNon-substrate0.894
CYP450 3A4 substrateNon-substrate0.7329
CYP450 1A2 substrateNon-inhibitor0.9467
CYP450 2C9 inhibitorNon-inhibitor0.961
CYP450 2D6 inhibitorNon-inhibitor0.9488
CYP450 2C19 inhibitorNon-inhibitor0.9639
CYP450 3A4 inhibitorNon-inhibitor0.8948
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.991
Ames testNon AMES toxic0.8878
CarcinogenicityNon-carcinogens0.8382
BiodegradationReady biodegradable0.9301
Rat acute toxicity1.6994 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9889
hERG inhibition (predictor II)Non-inhibitor0.964
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
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 tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Tricarboxylic acids and derivatives
Direct Parent
Tricarboxylic acids and derivatives
Alternative Parents
Beta hydroxy acids and derivatives / Monosaccharides / Alpha hydroxy acids and derivatives / Secondary alcohols / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Tricarboxylic acid or derivatives / Beta-hydroxy acid / Monosaccharide / Hydroxy acid / Alpha-hydroxy acid / Secondary alcohol / Carboxylic acid / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
isocitric acid (CHEBI:160)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nad binding
Specific Function
Not Available
Gene Name
icd
Uniprot ID
P08200
Uniprot Name
Isocitrate dehydrogenase [NADP]
Molecular Weight
45756.335 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]
Kind
Protein
Organism
Azotobacter vinelandii
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
icd
Uniprot ID
P16100
Uniprot Name
Isocitrate dehydrogenase [NADP]
Molecular Weight
80388.94 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate.
Gene Name
ACO2
Uniprot ID
Q99798
Uniprot Name
Aconitate hydratase, mitochondrial
Molecular Weight
85424.745 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
Human
Pharmacological action
Unknown
General Function
Nad binding
Specific Function
Plays a role in intermediary metabolism and energy production. It may tightly associate or interact with the pyruvate dehydrogenase complex.
Gene Name
IDH2
Uniprot ID
P48735
Uniprot Name
Isocitrate dehydrogenase [NADP], mitochondrial
Molecular Weight
50908.915 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
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Not Available
Gene Name
IDH1
Uniprot ID
O75874
Uniprot Name
Isocitrate dehydrogenase [NADP] cytoplasmic
Molecular Weight
46659.005 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific Function
Involved in the catabolism of short chain fatty acids (SCFA) via the 2-methylcitrate cycle I (propionate degradation route). Catalyzes the thermodynamically favored C-C bond cleavage of (2R,3S)-2-m...
Gene Name
prpB
Uniprot ID
P77541
Uniprot Name
2-methylisocitrate lyase
Molecular Weight
32134.305 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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:05