Common Name |
2-Hydroxydecanedioic acid
Description |
2-Hydroxydecanedioic acid appears in the urine of children affected with peroxisomal disorders such as urines of children with neonatal adrenoleukodystrophy and Zellweger syndrome and is a usefli marker for these diseases. (PMID 2943344 ).
Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms |
Value |
Source |
2-Hydroxy-decandioateHMDB
2-Hydroxy-decandioic acidHMDB
2-HydroxydecanedioateHMDB
2-HydroxysebacateHMDB
2-Hydroxysebacic acidHMDB
a-HydroxysebasateHMDB
a-Hydroxysebasic acidHMDB
alpha-HydroxysebasateHMDB
alpha-Hydroxysebasic acidHMDB
Chemical Formlia |
C10H18O5
Average Molecliar Weight |
218.2469
Monoisotopic Molecliar Weight |
218.115423686
IUPAC Name |
2-hydroxydecanedioic acid
Traditional Name |
2-hydroxysebacic acid
CAS Registry Number |
103963-71-9
SMILES |
OC(CCCCCCCC(O)=O)C(O)=O
InChI Identifier |
InChI=1S/C10H18O5/c11-8(10(14)15)6-4-2-1-3-5-7-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)
InChI Key |
LPIOYESQKJFWPQ-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
Monosaccharides
Dicarboxylic acids and derivatives
Alpha hydroxy acids and derivatives
Secondary alcohols
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Substituents |
Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Monosaccharide
Fatty acid
Fatty acyl
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic acyclic compound
Molecliar Framework |
Aliphatic acyclic compounds
External Descriptors |
Dicarboxylic acids (LMFA01170076 )
Ontology |
Status |
Detected and Quantified
Origin |
Endogenous
Biofunction |
Not Available
Application |
Not Available
Cellliar locations |
Cytoplasm
Physical Properties |
State |
Solid
Experimental Properties |
Property |
Value |
Reference |
Melting Point118 – 121 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties |
Property |
Value |
Source |
Water Solubility2.42 mg/mLALOGPS
logP0.87ALOGPS
logP1.4ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity52.64 m3·mol-1ChemAxon
Polarizability23.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
Spectra |
Spectra |
Spectrum Type |
Description |
Splash Key |
|
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
1D NMR |
1H NMR SpectrumNot Available
2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
Biological Properties |
Cellliar Locations |
Cytoplasm
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 Quantified0.39-0.67 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
27012787
details
UrineDetected and Quantified0.37-0.55 umol/mmol creatinineAdlit (>18 years old)MaleNormal
27012787
details
|
Abnormal Concentrations |
|
Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected but not Quantified Not AvailableNot AvailablePeroxisomal diseases
11978597
details
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 |
FDB022037
KNApSAcK ID |
Not Available
Chemspider ID |
113866
KEGG Compound ID |
Not Available
BioCyc ID |
Not Available
BiGG ID |
Not Available
Wikipedia Link |
Not Available
NuGOwiki Link |
HMDB00424
Metagene Link |
HMDB00424
METLIN ID |
5413
PubChem Compound |
128458
PDB ID |
Not Available
ChEBI ID |
Not Available
Product: Podocarpic acid
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 |
- Rocchiccioli F, Cartier PH, Aubourg P, Bougneres PF: Mass spectrometric identification of 2-hydroxy-sebacic acid in the urines of patients with neonatal adrenoleukodystrophy and Zellweger syndrome. Biomed Environ Mass Spectrom. 1986 Jun;13(6):315-8. [PubMed:2943344 ]
- Kajita M, Iwase K, Matsumoto M, Kuhara T, Sinka T, Matsumoto I: [Clinical and biochemical studies in a case of acute encephalopathy associated with calcium hopanthenate administration]. No To Hattatsu. 1990 May;22(3):267-73. [PubMed:2194543 ]
- Muth A, Jung J, Bilke S, Scharrer A, Mosandl A, Sewell AC, Bohles H: Simultaneous enantioselective analysis of chiral urinary metabolites in patients with Zellweger syndrome. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 25;792(2):269-77. [PubMed:12860034 ]
- Muth A, Mosandl A, Wanders RJ, Nowaczyk MJ, Baric I, Bohles H, Sewell AC: Stereoselective analysis of 2-hydroxysebacic acid in urine of patients with Zellweger syndrome and of premature infants fed with medium-chain triglycerides. J Inherit Metab Dis. 2003;26(6):583-92. [PubMed:14605504 ]
|
PMID: 9057848