You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameIsocitric Acid
Accession NumberDB01727  (EXPT01834)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIINot Available
CAS number320-77-4
WeightAverage: 192.1235
Monoisotopic: 192.02700261
Chemical FormulaC6H8O7
InChI KeyODBLHEXUDAPZAU-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]([[email protected]](CC(O)=O)C(O)=O)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Isocitrate dehydrogenase [NADP]ProteinunknownNot AvailableEscherichia coli (strain K12)P08200 details
Isocitrate dehydrogenase [NADP]ProteinunknownNot AvailableAzotobacter vinelandiiP16100 details
Aconitate hydratase, mitochondrialProteinunknownNot AvailableHumanQ99798 details
Isocitrate dehydrogenase [NADP], mitochondrialProteinunknownNot AvailableHumanP48735 details
Isocitrate dehydrogenase [NADP] cytoplasmicProteinunknownNot AvailableHumanO75874 details
2-methylisocitrate lyaseProteinunknownNot AvailableEscherichia coli (strain K12)P77541 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

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
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
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
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
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
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-methylisocitrate to yield pyruvate and succinate via an alpha-carboxy-carbanion intermediate.
Gene Name:
prpB
Uniprot ID:
P77541
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23