| Common Name |
3-Hydroxyadipic acid
| Description |
3-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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(3S)-3-HydroxyadipateHMDB
(3S)-3-Hydroxyadipic acidHMDB
3-HydroxyadipateHMDB
3-HydroxyhexanedioateHMDB
3-Hydroxyhexanedioic acidHMDB
| Chemical Formlia |
C6H10O5
| Average Molecliar Weight |
162.1406
| Monoisotopic Molecliar Weight |
162.05282343
| IUPAC Name |
3-hydroxyhexanedioic acid
| Traditional Name |
3-hydroxyadipic acid
| CAS Registry Number |
14292-29-6
| 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 Key |
YVOMYDHIQVMMTA-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Hydroxy acids and derivatives
| Direct Parent |
Medium-chain hydroxy acids and derivatives
| Alternative Parents |
Medium-chain fatty acids
Hydroxy fatty acids
Beta hydroxy acids and derivatives
Dicarboxylic acids and derivatives
Secondary alcohols
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Dicarboxylic acids (LMFA01170088 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0900000000-f33eb0251101e026565cView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-199210cf6818091d598cView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9400000000-4ea531d70611e020b9bfView in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm (predicted from logP)
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot Available
Normal
details
UrineDetected and Quantified3.1-6.0 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
27012787
details
UrineDetected and Quantified9.6 (3.2-31.2) umol/mmol creatinineNewborn (0-30 days old)BothNormal
8087979
details
UrineDetected and Quantified11.9 (3.8-43.6) umol/mmol creatinineInfant (0-1 year old)BothNormal
8087979
details
UrineDetected and Quantified2.2 (0.1-11.2) umol/mmol creatinineChildren (1-13 years old)Both
Normal
8087979
details
UrineDetected and Quantified1.7 (0.7-6.8) umol/mmol creatinineChildren (1-13 years old)Both
Normal
8087979
details
UrineDetected and Quantified1.4 (0.1-4.0) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
8087979
details
UrineDetected and Quantified4.2-5.7 umol/mmol creatinineAdlit (>18 years old)MaleNormal
27012787
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021968
| KNApSAcK ID |
Not Available
| Chemspider ID |
133894
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00345
| Metagene Link |
HMDB00345
| METLIN ID |
5334
| PubChem Compound |
151913
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Src Inhibitor 1
References |
| Synthesis Reference |
Chiruta, 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 |
- 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. [PubMed:8087979 ]
- 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. [PubMed:1444166 ]
- Svendsen JS, Whist JE, Sydnes LK: Absolute configuration of 3-hydroxyadipic acid in human urine. J Chromatogr. 1985 Jan 11;337(1):9-19. [PubMed:3980660 ]
- Tserng KY, Jin SJ: Metabolic origin of urinary 3-hydroxy dicarboxylic acids. Biochemistry. 1991 Mar 5;30(9):2508-14. [PubMed:2001377 ]
- Grupe A, Spiteller G: New polar acid metabolites in human urine. J Chromatogr. 1981 Dec 11;226(2):301-14. [PubMed:7320161 ]
- 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. [PubMed:2739576 ]
- 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. [PubMed:3168281 ]
|
PMID: 9134205