| Common Name |
3-Methyladipic acid
| Description |
3-Methyladipic acid is a metabolite of the catabolism of phytanic acid. Patients with adlit Refsums disease (ARD) are unable to detoxify phytanic acid by alpha-oxidation, and so the w-oxidation pathway is the only metabolic pathway available for phytanic acid degradation. This pathway produces 3-methyladipic acid as the final metabolite, which is excreted in the urine (Wanders et al. 2001). Activity of the w-oxidation pathway is approximately doubled in ARD patients compared with normal individuals (PMID: 11948235 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(+/-)-3-methyladipic acidHMDB
3-Methyl-hexanedioateHMDB
3-Methyl-hexanedioic acidHMDB
3-MethyladipateHMDB
3-MethylhexanedioateHMDB
3-Methylhexanedioic acidHMDB
b-Methyl-adipic acidHMDB
b-MethyladipateHMDB
b-Methyladipic acidHMDB
beta-Methyl-adipic acidHMDB
beta-MethyladipateHMDB
beta-Methyladipic acidHMDB
| Chemical Formlia |
C7H12O4
| Average Molecliar Weight |
160.1678
| Monoisotopic Molecliar Weight |
160.073558872
| IUPAC Name |
(3S)-3-methylhexanedioic acid
| Traditional Name |
(3S)-3-methylhexanedioic acid
| CAS Registry Number |
3058-01-3
| SMILES |
C[C@@H](CCC(O)=O)CC(O)=O
| InChI Identifier |
InChI=1S/C7H12O4/c1-5(4-7(10)11)2-3-6(8)9/h5H,2-4H2,1H3,(H,8,9)(H,10,11)/t5-/m0/s1
| InChI Key |
SYEOWUNSTUDKGM-YFKPBYRVSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Fatty Acyls
| Direct Parent |
Medium-chain fatty acids
| Alternative Parents |
Methyl-branched fatty acids
Dicarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Medium-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point101 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility248 mg/mL at 26 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility16.8 mg/mLALOGPS
logP0.65ALOGPS
logP0.78ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.29 m3·mol-1ChemAxon
Polarizability15.9 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, Negative (Annotated)splash10-0aos-3900000000-07aeef59ddcede42ebf4View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-0002-9100000000-c6e6e8dd79db7844b530View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-0frt-9200000000-2c314f5769b11dbbd837View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane
| Biofluid Locations |
Blood
Feces
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
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
20669995
details
UrineDetected and Quantified1.301 +/- 0.751 umol/mmol creatinineChildren (1 – 13 years old)Not Specified
Normal
Mordechai, Hien, …
details
UrineDetected but not Quantified Adlit (>18 years old)BothNormal
9439441
details
UrineDetected and Quantified0.72-1.5 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
27012787
details
UrineDetected and Quantified1.405 +/- 0.915 umol/mmol creatinineAdlit (>18 years old)BothNot Available
9439441
details
UrineDetected and Quantified92.32 +/- 18.25 umol/mmol creatinineChildren (1-13 years old)BothNormal
10731506
details
UrineDetected but not Quantified Adlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified2.9 (0.7-10.5) umol/mmol creatinineAdlit (>18 years old)BothNormal
6186413
details
UrineDetected and Quantified0.92-1.4 umol/mmol creatinineAdlit (>18 years old)MaleNormal
27012787
details
UrineDetected and Quantified9.2 (6.5-12.5) umol/mmol creatinineAdlit (>18 years old)BothNormal
Geigy Scientific …
details
UrineDetected and Quantified2.9 (1.1-7.2) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
UrineDetected and Quantified2.1 (0.9-5.6) umol/mmol creatinineAdlit (>18 years old)Both
Normal
24023812
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified4.116 +/- 3.618 umol/mmol creatinineChildren (1 – 13 years old)Not Specified
Eosinophilic esophagitis
Mordechai, Hien, …
details
UrineDetected and Quantified4.166 +/- 5.255 umol/mmol creatinineChildren (1 – 13 years old)Not Specified
Gastroesophageal reflux disease
Mordechai, Hien, …
details
UrineDetected and Quantified20.00 +/- 5.54 umol/mmol creatinineChildren (1-13 years old)BothMalnutrition (type kwashiorkor and marasmus)
10731506
details
UrineDetected and Quantified5.854 +/- 3.396 umol/mmol creatinineChildren (1 – 13 years old)Not Specified
Eosinophilic esophagitis
Mordechai, Hien, …
details
UrineDetected and Quantified5.9 (3.0-8.5) umol/mmol creatinineAdlit (>18 years old)BothRefsums disease
6186413
details
| Associated Disorders and Diseases |
| Disease References |
| Refsums disease |
- Greter J, Lindstedt S, Steen G: 2,6-Dimethyloctanedioic acid–a metabolite of phytanic acid in Refsums disease. Clin Chem. 1983 Mar;29(3):434-7. [PubMed:6186413 ]
| Associated OMIM IDs |
266500 (Refsum's disease)
| 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 |
FDB022115
| KNApSAcK ID |
Not Available
| Chemspider ID |
5367267
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00555
| Metagene Link |
HMDB00555
| METLIN ID |
3797
| PubChem Compound |
6999745
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Beta-Sitosterol
References |
| Synthesis Reference |
Vogel, Arthur I. Syntheses of cyclic compounds. VIII. Conversion of b-methyladipic acid into 3-methylcyclopentanone and the preparation of 3-methylcyclopentane-1,1-diacetic acid. Journal of the Chemical Society (1931), 907-14. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Wierzbicki AS, Lloyd MD, Schofield CJ, Feher MD, Gibberd FB: Refsums disease: a peroxisomal disorder affecting phytanic acid alpha-oxidation. J Neurochem. 2002 Mar;80(5):727-35. [PubMed:11948235 ]
|
PMID: 8938726