MiMeDB: Showing metabocard for 3-Carboxy-3-hydroxy-4-methylpentanoate (MMDBc0049883)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:29 UTC

Update Date

2022-12-15 22:52:19 UTC

Metabolite ID

MMDBc0049883

Metabolite Identification

Common Name

3-Carboxy-3-hydroxy-4-methylpentanoate

Description

2-Isopropylmalic acid (CAS: 3237-44-3), also known as 3-carboxy-3-hydroxyisocaproic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Isopropylmalic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Isopropylmalic acid is an alpha-hydroxy organic acid regularly occurring in the urine of healthy individuals (PMID: 2338430 , 544608 ), and in hemofiltrates (PMID: 7251751 ). 2-Isopropylmalic acid is elevated during fasting and diabetic ketoacidosis (PMID: 1591279 ). It is also a metabolite found in Acetobacter (PMID: 6035258 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      19.714 -16.367   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.044 -15.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.384 -15.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.714 -17.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.381 -16.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.047 -16.367   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.384 -14.061   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.455 -18.674   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.051 -18.674   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.417 -18.044   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.712 -15.596   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      20.894 -17.118   0.000  0.00  0.00           O+0
CONECT    1    2    3    4   12                                             
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
(2S)-2-Hydroxy-2-isopropylsuccinic acid	ChEBI
(2S)-2-Isopropylmalate	ChEBI
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoic acid	ChEBI
(3S)-3-Carboxy-3-hydroxyisocaproic acid	ChEBI
(S)-2-Hydroxy-2-(isopropyl)succinic acid	ChEBI
3-Carboxy-3-hydroxy-4-methylpentanoate	ChEBI
3-Carboxy-3-hydroxyisocaproate	ChEBI
(2S)-2-Hydroxy-2-isopropylsuccinate	Generator
(2S)-2-Isopropylmalic acid	Generator
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoate	Generator
(3S)-3-Carboxy-3-hydroxyisocaproate	Generator
(S)-2-Hydroxy-2-(isopropyl)succinate	Generator
3-Carboxy-3-hydroxy-4-methylpentanoic acid	Generator
3-Carboxy-3-hydroxyisocaproic acid	Generator
2-Isopropylmalate	Generator
2-Hydroxy-2-isopropylsuccinate	HMDB
2-Hydroxy-2-isopropylsuccinic acid	HMDB
2-Isopropyl-2-hydroxybutanedioate	HMDB
2-Isopropyl-2-hydroxybutanedioic acid	HMDB
2-Isopropyl-malic acid	HMDB
a-Isopropylmalate	HMDB
a-Isopropylmalic acid	HMDB
alpha-Isopropylmalate	HMDB
alpha-Isopropylmalic acid	HMDB
(2S)-2-Hydroxy-2-(1-methylethyl)butanedioic acid	HMDB
(2S)-2-Hydroxy-2-(propan-2-yl)butanedioic acid	HMDB
(S)-(+)-2-Isopropylmalic acid	HMDB
2-Hydroxy-2-(1-methylethyl)butanedioic acid	HMDB
Α-isopropylmalate	HMDB
Α-isopropylmalic acid	HMDB
2-Isopropylmalic acid	HMDB

Molecular Formula

C₇H₁₂O₅

Average Mass

176.1672

Monoisotopic Mass

176.068473494

IUPAC Name

(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid

Traditional Name

2-isopropyl-malic acid

CAS Registry Number

Not Available

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

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-isopropylmalic acid (CHEBI:35128 )
Dicarboxylic acids (LMFA01170083 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	181 g/L	ALOGPS
logP	-0.29	ALOGPS
logP	0.21	ChemAxon
logS	0.01	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.58 m³·mol⁻¹	ChemAxon
Polarizability	16.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-1c869c73651e7e4e5dda	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00bl-9134000000-30fabfd0c26c38444fff	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-004i-0900000000-1bb48f5ddadbf88b8f6c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00kr-9400000000-5df8f3f29d2e8a962cac	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-05n0-9200000000-c62b1543d0e6a41388f1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014r-6900000000-983e4a8edd0725d26979	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-016r-1900000000-5aa4d41c6ff31081d9d7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9200000000-d4b84f7b5f2a53ac5800	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-c680094e514a83eea978	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-052o-9000000000-365c84abb7ec259fb43e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e28ea8cd657f96ff8357	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0690-1900000000-3b83300261e0daab2ef1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9700000000-2652db028b01706ac042	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9300000000-808bda4307e96bcfcc83	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-2900000000-9fa33cd594a81b5d67cd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-055r-9700000000-8ab90438d0e6c9b7d0be	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9100000000-41e1c40b755f8bfaf000	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01x9-9800000000-53afadde706df1ef69ab	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-4bfe3581b4b94540fea0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1470f6a6a1859e452712	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-9a718ee22b675ce18980	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-8900000000-188b5287c7dbbce2559f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9000000000-2a93d25f081bcaa86a53	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007038	3-Carboxy-3-hydroxy-4-methylpentanoate	alpha-Ketoisovaleric acid	Not Available	3-methyl-2-oxobutanoate synthase	VMH	30371894
MMDBr0007076	2-Isopropylmaleate	3-Carboxy-3-hydroxy-4-methylpentanoate	Not Available	2-isopropylmalate hydratase	VMH	30371894
MMDBr0008440	alpha-Ketoisovaleric acid	3-Carboxy-3-hydroxy-4-methylpentanoate	Not Available	2-isopropylmalate synthase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	266	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	174	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	117	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	93	Human feces; Human appendix biopsy; Human ; Human stool; Human urine; Human gastric fluid; Human saliva	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	4	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Saliva	Detected and Quantified	0.114	0.0493	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.159	0.0746	uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.218	0.138	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.247	0.161	uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.

External Links

HMDB ID

HMDB0000402

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

3-CARBOXY-3-HYDROXY-ISOCAPROATE

BiGG ID

Not Available

Wikipedia Link

Isopropylmalic acid

METLIN ID

339

PubChem Compound

5280523

PDB ID

Not Available

ChEBI ID

35128

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Spiteller M, Spiteller G: [Occurrence of alpha-alkyl-substituted malic acids, and beta-hydroxy-beta-alkyl-substituted dicarboxylic and tricarboxylic acid derivatives in normal urine (author's transl)]. J Chromatogr. 1979 Nov 11;164(3):319-29. [PubMed:544608 ]
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. doi: 10.1002/bms.1200210107. [PubMed:1591279 ]
Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. doi: 10.1016/s0378-4347(00)83375-7. [PubMed:2338430 ]
Maragoudakis ME, Strassman M: Biosynthesis of alpha-isopropylmalic and citric acids in Acetobacter suboxydans. J Bacteriol. 1967 Sep;94(3):512-6. doi: 10.1128/jb.94.3.512-516.1967. [PubMed:6035258 ]
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. doi: 10.1016/s0378-4347(00)80063-8. [PubMed:7251751 ]

Showing metabocard for 3-Carboxy-3-hydroxy-4-methylpentanoate (MMDBc0049883)

MOL for #<Metabolite:0x00007f5aa1aab0d8>

3D MOL for #<Metabolite:0x00007f5aa1aab0d8>

3D SDF for #<Metabolite:0x00007f5aa1aab0d8>

3D-SDF for #<Metabolite:0x00007f5aa1aab0d8>

PDB for #<Metabolite:0x00007f5aa1aab0d8>

3D PDB for #<Metabolite:0x00007f5aa1aab0d8>

SMILES for #<Metabolite:0x00007f5aa1aab0d8>

INCHI for #<Metabolite:0x00007f5aa1aab0d8>

Structure for #<Metabolite:0x00007f5aa1aab0d8>

3D Structure for #<Metabolite:0x00007f5aa1aab0d8>