| 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