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Record Information
Version1.0
Created at2020-03-18 23:22:03 UTC
Updated at2022-12-13 23:36:28 UTC
CannabisDB IDCDB006159
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCitric acid
Description
Structure
Thumb
Synonyms
Chemical FormulaC6H8O7
Average Molecular Weight192.12
Monoisotopic Molecular Weight192.027
IUPAC Name2-hydroxypropane-1,2,3-tricarboxylic acid
Traditional Namecitric acid
CAS Registry Number77-92-9
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChI KeyKRKNYBCHXYNGOX-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling Point310 °CWikipedia
Water Solubility592 mg/mLNot Available
logP-1.64AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-1.3ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.62 m³·mol⁻¹ChemAxon
Polarizability15.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Pyruvate dehydrogenase E1 component subunit beta, mitochondrialPDHB3p21.1-p14.2P11177 details
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1Xp22.1P08559 details
Aspartate aminotransferase, mitochondrialGOT216q21P00505 details
Aconitate hydratase, mitochondrialACO222q13.2Q99798 details
Cytoplasmic aconitate hydrataseACO19p21.1P21399 details
6-phosphofructokinase, liver typePFKL21q22.3P17858 details
Polycystic kidney disease 2-like 1 proteinPKD2L110q24Q9P0L9 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytoplasmic aconitate hydrataseACO19p21.1P21399 details
6-phosphofructokinase, liver typePFKL21q22.3P17858 details
Polycystic kidney disease 2-like 1 proteinPKD2L110q24Q9P0L9 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified6.7628 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified4.415 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified6.282 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified1.983 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified11.393 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified4.0481 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0000094
DrugBank IDDB04272
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030735
KNApSAcK IDC00007619
Chemspider ID305
KEGG Compound IDC00158
BioCyc IDCIT
BiGG ID34080
Wikipedia LinkCitric_Acid
METLIN ID124
PubChem Compound311
PDB IDNot Available
ChEBI ID30769
References
General References
  1. Ren JG, Seth P, Ye H, Guo K, Hanai JI, Husain Z, Sukhatme VP: Citrate Suppresses Tumor Growth in Multiple Models through Inhibition of Glycolysis, the Tricarboxylic Acid Cycle and the IGF-1R Pathway. Sci Rep. 2017 Jul 3;7(1):4537. doi: 10.1038/s41598-017-04626-4. [PubMed:28674429 ]
  2. Caudarella R, Vescini F, Buffa A, Stefoni S: Citrate and mineral metabolism: kidney stones and bone disease. Front Biosci. 2003 Sep 1;8:s1084-106. doi: 10.2741/1119. [PubMed:12957820 ]
  3. Costello LC, Franklin RB: Testosterone and prolactin regulation of metabolic genes and citrate metabolism of prostate epithelial cells. Horm Metab Res. 2002 Aug;34(8):417-24. doi: 10.1055/s-2002-33598. [PubMed:12198595 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHB
Uniprot ID:
P11177
Molecular weight:
39233.1
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHA1
Uniprot ID:
P08559
Molecular weight:
43295.255
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
General function:
Involved in metabolic process
Specific function:
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO2
Uniprot ID:
Q99798
Molecular weight:
85424.745
General function:
Involved in metabolic process
Specific function:
Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding. Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO1
Uniprot ID:
P21399
Molecular weight:
98398.14
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKL
Uniprot ID:
P17858
Molecular weight:
85017.825
General function:
Involved in calcium ion binding
Specific function:
May function as a subunit of an ion channel and act as a transducer of calcium-mediated signaling
Gene Name:
PKD2L1
Uniprot ID:
Q9P0L9
Molecular weight:
91981.2