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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-06-10 21:22:04 UTC
HMDB IDHMDB00345
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxyadipic acid
Description3-Hydroxyadipic acid is a normal urinary dicarboxylic acid derived from the omega-oxidation of 3-hydroxy fatty acids and the subsequent beta-oxidation of longer chain 3-hydroxy dicarboxylic acids (PMID 2001377 ). It is found to be elevated in patients with 3-hydroxydicarboxylic aciduria (PMID 1444166 ) and non-ketotic hypoglycemia (PMID 3168281 ).
Structure
Thumb
Synonyms
ValueSource
(3S)-3-HydroxyadipateHMDB
(3S)-3-Hydroxyadipic acidHMDB
3-HydroxyadipateHMDB
3-HydroxyhexanedioateHMDB
3-Hydroxyhexanedioic acidHMDB
Chemical FormulaC6H10O5
Average Molecular Weight162.1406
Monoisotopic Molecular Weight162.05282343
IUPAC Name3-hydroxyhexanedioic acid
Traditional Name3-hydroxyadipic acid
CAS Registry Number14292-29-6
SMILES
OC(CCC(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C6H10O5/c7-4(3-6(10)11)1-2-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)
InChI KeyInChIKey=YVOMYDHIQVMMTA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility88.2 mg/mLALOGPS
logP-0.89ALOGPS
logP-0.74ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.25 m3·mol-1ChemAxon
Polarizability14.78 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0900000000-f33eb0251101e026565cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-199210cf6818091d598cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9400000000-4ea531d70611e020b9bfView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified3.1-6.0 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified9.6 (3.2-31.2) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified11.9 (3.8-43.6) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified2.2 (0.1-11.2) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.7 (0.7-6.8) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.4 (0.1-4.0) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified4.2-5.7 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021968
KNApSAcK IDNot Available
Chemspider ID133894
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00345
Metagene LinkHMDB00345
METLIN ID5334
PubChem Compound151913
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceChiruta, Chandramouli; Jachak, Santosh; Clive, Derrick L. J. A convenient general method for the synthesis of hydroxy diacids. Tetrahedron Letters (2007), 48(18), 3141-3143.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  2. Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. [1444166 ]
  3. Svendsen JS, Whist JE, Sydnes LK: Absolute configuration of 3-hydroxyadipic acid in human urine. J Chromatogr. 1985 Jan 11;337(1):9-19. [3980660 ]
  4. Tserng KY, Jin SJ: Metabolic origin of urinary 3-hydroxy dicarboxylic acids. Biochemistry. 1991 Mar 5;30(9):2508-14. [2001377 ]
  5. Grupe A, Spiteller G: New polar acid metabolites in human urine. J Chromatogr. 1981 Dec 11;226(2):301-14. [7320161 ]
  6. Tserng KY, Jin SJ, Hoppel CL, Kerr DS, Genuth SM: Urinary 3-hydroxyadipic acid 3,6-lactone: structural identification and effect of fasting in adults and children. Metabolism. 1989 Jul;38(7):655-61. [2739576 ]
  7. Kelley RI, Morton DH: 3-Hydroxyoctanoic aciduria: identification of a new organic acid in the urine of a patient with non-ketotic hypoglycemia. Clin Chim Acta. 1988 Jun 30;175(1):19-26. [3168281 ]