Isocitric Acid

HCID 1198

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Basic information

CAS: 320-77-4
Standard SMILES: O=C(O)CC(C(=O)O)C(O)C(=O)O
InChIKey: ODBLHEXUDAPZAU-UHFFFAOYSA-N
Molecular formula: C6H8O7
Average molar mass: 192.12 g/mol
Monoisotopic mass: 192.02700259

Names & identifiers

Preferred name: Isocitric Acid
IUPAC: 1-hydroxypropane-1,2,3-tricarboxylic acid
English name: 3-carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid
Molecular formula: C6H8O7
Molecular weight: 192.12

Names & synonyms

isocitric acid320-77-41-Hydroxypropane-1,2,3-tricarboxylic acid3-carboxy-2,3-dideoxypentaric acid1-Hydroxytricarballylic acid9RW6G5D4MQCHEBI:30887DTXSID10415742RefChem:923656DTXCID40366591206-282-3isocitrate

Show more names

isocitricaci3-carboxy-2-hydroxypentane-1,5-dioic acid

DL-Isocitric acid3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acidI-CIT1-Hydroxy-1,2,3-propanetricarboxylic acidD-isocitratepentaric acid, 3-carboxy-2,3-dideoxy-Isocitrate acidiso citric acid

Database identifiers

CAS: 320-77-4
PubChem CID: 1198
DTXSID: DTXSID60861871
ChEMBL: CHEMBL390356、CHEMBL539669
ChEBI: CHEBI:30887
UNII: 9RW6G5D4MQ
EC Number: 206-282-3
Nikkaji: J95.796H

Properties

Computed structural properties

XLogP: -1.8
Topological polar surface area: 132 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 7
Rotatable bonds: 5
Heavy atoms: 13
Formal charge: 0
Complexity: 233

Experimental & physicochemical properties

Solubility466 mg/mL

Melting Point162 - 165 °C

Physical DescriptionSolid

Collision Cross Section · 4 items

136.4 Å² [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；142.7 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；127 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

125.26 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

130.03 Å² [M-H]- [CCS Type: DT; Method: stepped-field]；146.78 Å² [M+Na]+ [CCS Type: DT; Method: stepped-field]

142.8 Å² [M+Na]+；136.5 Å² [M-2H+Na]-；127.3 Å² [M-H]-

Physicochemical properties

Melting point: 105 °C · 105°C
Boiling point: 248.08 °C · 248.08°C (rough estimate)
Density: 1.4845 · 1.4845 (rough estimate)
refractive index: 1.4455 · 1.4455 (estimate)
pka: 3.4 · 3.40±0.34(Predicted)
form: Solid
color: White to off-white
FDA UNII: 9 RW6G5D4MQ · 9RW6G5D4MQ

Chemistry & industry

Pharmacology

Tissue LocationsAdrenal Gland

Cellular LocationsCytoplasm；Mitochondria；Peroxisome

Metabolite Pathways · 1 item

2-ketoglutarate dehydrogenase complex deficiency；Citric Acid Cycle；Congenital lactic acidosis；Fumarase deficiency；Glutaminolysis and Cancer；Mitochondrial complex II deficiency；Pyruvate dehydrogenase deficiency (E2)；Pyruvate dehydrogenase deficiency (E3)；The oncogenic action of 2-hydroxyglutarate；The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria ；Total 14 pathways, visit the HMDB page for details

Applications

UsesIsocitric Acid-13C4 is an isotopic labeled compound of 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid(C279625); used in the preparation of optically active isocitric acid from Bryophyllum leaf tissues.