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Identification
YMDB IDYMDB00144
NameHomoisocitric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionHomoisocitric acid is an intermediate in lysine biosynthesis pathway. S. cerevisiae synthesizes the essential amino acid L-lysine via the L-alpha-aminoadipate pathway instead of the diaminopimelate pathway. [Biocyc LYSINE-AMINOAD-PWY]
Structure
Thumb
Synonyms
  • (-)-1-Hydroxy-1,2,4-butanetricarboxylate
  • (1R,2S)-1-Hydroxybutane-1,2,4-tricarboxylate
  • 1-Hydroxybutane-1,2,4-tricarboxylate
  • 3-Carboxy-2-hydroxyadipate
  • Homoisocitrate
  • (-)-threo-Homoisocitrate
  • 3-Carboxy-2-hydroxyadipic acid
  • Homoisocitric acid
  • (-)-1-Hydroxy-1,2,4-butanetricarboxylic acid
  • (1R,2S)-1-Hydroxybutane-1,2,4-tricarboxylic acid
  • (-)-threo-Homoisocitric acid
CAS numberNot Available
WeightAverage: 206.1501
Monoisotopic: 206.042652674
InChI KeyOEJZZCGRGVFWHK-WVZVXSGGSA-N
InChIInChI=1S/C7H10O7/c8-4(9)2-1-3(6(11)12)5(10)7(13)14/h3,5,10H,1-2H2,(H,8,9)(H,11,12)(H,13,14)/t3-,5+/m0/s1
IUPAC Name(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylic acid
Traditional IUPAC Name(-)-homoisocitric acid
Chemical FormulaC7H10O7
SMILESO[C@H]([C@H](CCC(O)=O)C(O)=O)C(O)=O
Chemical 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
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility26.2 g/LALOGPS
logP-0.54ALOGPS
logP-1ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)3.12ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.32 m³·mol⁻¹ChemAxon
Polarizability17.63 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Lysine biosynthesisec00300 Map00300
SMPDB ReactionsNot Available
KEGG Reactions
but-1-ene-1,2,4-tricarboxylic acid + waterHomoisocitric acid
NAD + Homoisocitric acidNADH + 2-Oxaloglutaric acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Strassman, M., Ceci, L. N. (1965). "Enzymatic formation of alpha-ketoadipic acid from homoisocitric acid." J Biol Chem 240:4357-4361.4284830
  • Zabriskie, T. M., Jackson, M. D. (2000). "Lysine biosynthesis and metabolism in fungi." Nat Prod Rep 17:85-97.10714900
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID30903
HMDB IDNot Available
Pubchem Compound ID5460287
Kegg IDC05662
ChemSpider ID21865262
FOODB IDNot Available
Wikipedia IDHomoisocitric acid
BioCyc IDNot Available

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the NAD(+)-dependent conversion of homoisocitrate to alpha-ketoadipate
Gene Name:
LYS12
Uniprot ID:
P40495
Molecular weight:
40068.60156
Reactions
(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate + NAD(+) → 2-oxoadipate + CO(2) + NADH.
General function:
Involved in metabolic process
Specific function:
Responsible for the dehydration of cis-homoaconitate to homoisocitric acid
Gene Name:
LYS4
Uniprot ID:
P49367
Molecular weight:
75150.10156
Reactions
(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate → (Z)-but-1-ene-1,2,4-tricarboxylate + H(2)O.