| Common Name |
2-Isopropylmalic acid
| Description |
2-Isopropylmalic acid is an alpha-hydroxy organic acid regliarly occurring in urine of healthy individuals (PMIDs 2338430, 544608), and in hemofiltrates. (PMID 7251751 ) 2-Isopropylmalic acid is elevated during fasting and diabetic ketoacidosis. (PMID 1591279 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(2S)-2-Hydroxy-2-isopropylsuccinic acidChEBI
(2S)-2-IsopropylmalateChEBI
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoic acidChEBI
(3S)-3-Carboxy-3-hydroxyisocaproic acidChEBI
(S)-2-Hydroxy-2-(isopropyl)succinic acidChEBI
3-Carboxy-3-hydroxy-4-methylpentanoateChEBI
3-Carboxy-3-hydroxyisocaproateChEBI
(2S)-2-Hydroxy-2-isopropylsuccinateGenerator
2-IsopropylmalateGenerator
(2S)-2-Isopropylmalic acidGenerator
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoateGenerator
(3S)-3-Carboxy-3-hydroxyisocaproateGenerator
(S)-2-Hydroxy-2-(isopropyl)succinateGenerator
3-Carboxy-3-hydroxy-4-methylpentanoic acidGenerator
3-Carboxy-3-hydroxyisocaproic acidGenerator
2-Hydroxy-2-isopropylsuccinateHMDB
2-Hydroxy-2-isopropylsuccinic acidHMDB
2-Isopropyl-2-hydroxybutanedioateHMDB
2-Isopropyl-2-hydroxybutanedioic acidHMDB
2-Isopropyl-malic acidHMDB
a-IsopropylmalateHMDB
a-Isopropylmalic acidHMDB
alpha-IsopropylmalateHMDB
alpha-Isopropylmalic acidHMDB
| Chemical Formlia |
C7H12O5
| Average Molecliar Weight |
176.1672
| Monoisotopic Molecliar Weight |
176.068473494
| IUPAC Name |
(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
| Traditional Name |
2-isopropyl-malic acid
| CAS Registry Number |
3237-44-3
| SMILES |
CC(C)[C@@](O)(CC(O)=O)C(O)=O
| InChI Identifier |
InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1
| InChI Key |
BITYXLXUCSKTJS-ZETCQYMHSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Fatty Acyls
| Direct Parent |
Hydroxy fatty acids
| Alternative Parents |
Short-chain hydroxy acids and derivatives
Methyl-branched fatty acids
Dicarboxylic acids and derivatives
Alpha hydroxy acids and derivatives
Tertiary alcohols
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Branched fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Tertiary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
2-isopropylmalic acid (CHEBI:35128 )
Dicarboxylic acids (LMFA01170083 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Microbial
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point144 – 146 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility181.0 mg/mLALOGPS
logP-0.29ALOGPS
logP0.21ChemAxon
logS0.01ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.58 m3·mol-1ChemAxon
Polarizability16.37 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted GC-MS |
Predicted GC-MS Spectrum – GC-MSNot Available
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0900000000-1bb48f5ddadbf88b8f6cView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-00kr-9400000000-5df8f3f29d2e8a962cacView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-05n0-9200000000-c62b1543d0e6a41388f1View in MoNA
| 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 |
Feces
Saliva
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
FecesDetected but not Quantified Infant (0-1 year old)Not AvailableNormal
24628373
details
SalivaDetected and Quantified0.114 +/- 0.0493 uMAdlit (>18 years old)Not Specified
Normal
Sugimoto et al. (…
details
SalivaDetected and Quantified0.159 +/- 0.0746 uMAdlit (>18 years old)Female
Normal
Sugimoto et al. (…
details
SalivaDetected and Quantified0.218 +/- 0.138 uMAdlit (>18 years old)Not Specified
Normal
Sugimoto et al. (…
details
SalivaDetected and Quantified0.247 +/- 0.161 uMAdlit (>18 years old)Male
Normal
Sugimoto et al. (…
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 |
FDB011983
| KNApSAcK ID |
C00019690
| Chemspider ID |
4444155
| KEGG Compound ID |
C02504
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00402
| Metagene Link |
HMDB00402
| METLIN ID |
339
| PubChem Compound |
5280523
| PDB ID |
Not Available
| ChEBI ID |
35128
Product: EGF816 (S-enantiomer)
References |
| Synthesis Reference |
Schloss J V; Magolda R; Emptage M Synthesis of alpha-isopropylmalate, beta-isopropylmalate, and dimethylcitraconate. Methods in enzymology (1988), 166 92-6. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Verhaeghe BJ, Van Bocxlaer JF, De Leenheer AP: Gas chromatographic/mass spectrometric identification of 3-hydroxydicarboxylic acids in urine. Biol Mass Spectrom. 1992 Jan;21(1):27-32. [PubMed:1591279 ]
- Pinkston D, Spiteller G, Von Henning H, Matthaei D: High resolution gas chromatography mass spectrometry of the methyl esters of organic acids from uremic hemofiltrates. J Chromatogr. 1981 Apr 10;223(1):1-19. [PubMed:7251751 ]
|
PMID: 26193352