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Homocitric acid: Difference between revisions

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Revision as of 09:39, 18 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Revision as of 09:45, 12 February 2012 edit undoThe chemistds (talk | contribs)Extended confirmed users5,761 edits added PubchemID, CSID, (Std)InChI & (Std)InChIKeyNext edit →
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| CASNo=3562-74-1 | CASNo=3562-74-1
| PubChem=28371 | PubChem=28371
| ChemSpiderID = 26392
| SMILES=OC(=O)CCC(O)(CC(O)=O)C(O)=O | SMILES = O=C(O)CC(O)(C(=O)O)CCC(=O)O
| InChI = 1/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13)
| InChIKey = XKJVEVRQMLKSMO-UHFFFAOYAL
| StdInChI = 1S/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13)
| StdInChIKey = XKJVEVRQMLKSMO-UHFFFAOYSA-N
}} }}
|Section2= {{Chembox Properties |Section2= {{Chembox Properties

Revision as of 09:45, 12 February 2012

Homocitric acid
Names
IUPAC name 2-hydroxybutane-1,2,4-tricarboxylic acid
Other names Homocitric acid
Homocitrate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13)Key: XKJVEVRQMLKSMO-UHFFFAOYSA-N
  • InChI=1/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13)Key: XKJVEVRQMLKSMO-UHFFFAOYAL
SMILES
  • O=C(O)CC(O)(C(=O)O)CCC(=O)O
Properties
Chemical formula C7H10O7
Molar mass 206.15 g/mol
Appearance colorless solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Homocitric acid is an organic compound with the formula HOC(CO2H)(CH2CO2H)(C2H4CO2H). This tricarboxylic acid occurs naturally as a component of the iron-molybdenum cofactor of certain nitrogenase proteins. Biochemists often refer to this cofactor as homocitrate, which is the conjugate bases that predominate in neutral aqueous solutions of this species.

The molecule is related to citric acid by the addition of one methylene group, which is implied with the term "homo." Unlike citric acid, homocitric acid is chiral. The acid exists in equilibrium with the lactone.


References

  1. Douglas C. Rees "Great Metalloclusters in Enzymology" Annual Reviews of Biochemistry 2002, volume 71, pp. 221–46. doi:10.1146/annurev.biochem.71.110601.135406


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