Isocitric Acid
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Identification
- Generic Name
- Isocitric Acid
- DrugBank Accession Number
- DB01727
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 192.1235
Monoisotopic: 192.02700261 - Chemical Formula
- C6H8O7
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UIsocitrate dehydrogenase [NADP] Not Available Escherichia coli (strain K12) UIsocitrate dehydrogenase [NADP] Not Available Azotobacter vinelandii UAconitate hydratase, mitochondrial Not Available Humans UIsocitrate dehydrogenase [NADP], mitochondrial Not Available Humans UIsocitrate dehydrogenase [NADP] cytoplasmic Not Available Humans U2-methylisocitrate lyase Not Available Escherichia 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 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
- Alcohol / Aliphatic acyclic compound / Alpha-hydroxy acid / Beta-hydroxy acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Hydroxy acid / Monosaccharide / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- isocitric acid (CHEBI:160)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9RW6G5D4MQ
- CAS number
- 320-77-4
- 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
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
- PDB Entries
- 5fy8
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 52.5 mg/mL ALOGPS logP -0.35 ALOGPS logP -1.4 Chemaxon logS -0.56 ALOGPS pKa (Strongest Acidic) 3.07 Chemaxon pKa (Strongest Basic) -4 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 132.13 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 35.72 m3·mol-1 Chemaxon Polarizability 15.58 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6961 Blood Brain Barrier + 0.7646 Caco-2 permeable - 0.8985 P-glycoprotein substrate Non-substrate 0.68 P-glycoprotein inhibitor I Non-inhibitor 0.9716 P-glycoprotein inhibitor II Non-inhibitor 0.9632 Renal organic cation transporter Non-inhibitor 0.9625 CYP450 2C9 substrate Non-substrate 0.8608 CYP450 2D6 substrate Non-substrate 0.894 CYP450 3A4 substrate Non-substrate 0.7329 CYP450 1A2 substrate Non-inhibitor 0.9467 CYP450 2C9 inhibitor Non-inhibitor 0.961 CYP450 2D6 inhibitor Non-inhibitor 0.9488 CYP450 2C19 inhibitor Non-inhibitor 0.9639 CYP450 3A4 inhibitor Non-inhibitor 0.8948 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.991 Ames test Non AMES toxic 0.8878 Carcinogenicity Non-carcinogens 0.8382 Biodegradation Ready biodegradable 0.9301 Rat acute toxicity 1.6994 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9889 hERG inhibition (predictor II) Non-inhibitor 0.964
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00ba-7900000000-96194d87d52b155cf1b9 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-056r-0900000000-cb834774e6d1031ba9fe Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0900000000-42be0d463ae704d6897a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0ufr-2900000000-987dfb81434f748677a5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0uk9-4900000000-e6455a36f7fae24b017d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0kml-9200000000-34c34857312fba6e8de8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9200000000-bedebab7f1d693aca971 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 139.6982829 predictedDarkChem Lite v0.1.0 [M-H]- 136.06714 predictedDeepCCS 1.0 (2019) [M+H]+ 141.2378829 predictedDarkChem Lite v0.1.0 [M+H]+ 138.4627 predictedDeepCCS 1.0 (2019) [M+Na]+ 139.9970829 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.43996 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsIsocitrate dehydrogenase [NADP]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- guanosine tetraphosphate binding
- Gene Name
- icd
- Uniprot ID
- P08200
- Uniprot Name
- Isocitrate dehydrogenase [NADP]
- Molecular Weight
- 45756.335 Da
References
2. DetailsIsocitrate dehydrogenase [NADP]
- Kind
- Protein
- Organism
- Azotobacter vinelandii
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- isocitrate dehydrogenase (NADP+) activity
- Gene Name
- icd
- Uniprot ID
- P16100
- Uniprot Name
- Isocitrate dehydrogenase [NADP]
- Molecular Weight
- 80388.94 Da
References
3. DetailsAconitate hydratase, mitochondrial
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the isomerization of citrate to isocitrate via cis-aconitate
- Specific Function
- 3 iron, 4 sulfur cluster binding
- Gene Name
- ACO2
- Uniprot ID
- Q99798
- Uniprot Name
- Aconitate hydratase, mitochondrial
- Molecular Weight
- 85424.745 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Plays a role in intermediary metabolism and energy production (PubMed:19228619, PubMed:22416140). It may tightly associate or interact with the pyruvate dehydrogenase complex (PubMed:19228619, PubMed:22416140)
- Specific Function
- isocitrate dehydrogenase (NADP+) activity
- Gene Name
- IDH2
- Uniprot ID
- P48735
- Uniprot Name
- Isocitrate dehydrogenase [NADP], mitochondrial
- Molecular Weight
- 50908.915 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the NADP(+)-dependent oxidative decarboxylation of isocitrate (D-threo-isocitrate) to 2-ketoglutarate (2-oxoglutarate), which is required by other enzymes such as the phytanoyl-CoA dioxygenase (PubMed:10521434, PubMed:19935646). Plays a critical role in the generation of NADPH, an important cofactor in many biosynthesis pathways (PubMed:10521434). May act as a corneal epithelial crystallin and may be involved in maintaining corneal epithelial transparency (By similarity)
- Specific Function
- cadherin binding
- Gene Name
- IDH1
- Uniprot ID
- O75874
- Uniprot Name
- Isocitrate dehydrogenase [NADP] cytoplasmic
- Molecular Weight
- 46659.005 Da
References
6. Details2-methylisocitrate lyase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General 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.
- Specific Function
- magnesium ion binding
- Gene Name
- prpB
- Uniprot ID
- P77541
- Uniprot Name
- 2-methylisocitrate lyase
- Molecular Weight
- 32134.305 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51