MiMeDB: Showing metabocard for 3-Carboxy-3-hydroxy-isocaproate (MMDBc0029761)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:40:32 UTC

Update Date

2022-08-31 17:16:45 UTC

MiMeDB ID

MMDBc0029761

Metabolite Identification

Common Name

3-Carboxy-3-hydroxy-isocaproate

Description

3-carboxy-3-hydroxy-isocaproate is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. Alpha isopropylmalate is involved in the biosynthesis of leucine. The protein product of MJ0720 was found to be alpha-isopropylmalate dehydrogenase (LeuB) and was found to catalyze the NAD-dependent decarboxylation of one isomer of DL-threo-isopropylmalate to 2-ketoisocaproate; thus, it is involved in the biosynthesis of leucine. (PMID 10940051 )

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.541   3.850   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0       0.206   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    5    7                                                       
CONECT    4    1    2    7                                                  
CONECT    5    3    8    9                                                  
CONECT    6    7   10   11                                                  
CONECT    7    3    4    6   12                                             
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
2-Hydroxy-2-isopropylsuccinate	ChEBI
3-Carboxy-3-hydroxy-4-methylpentanoate	ChEBI
3-Carboxy-3-hydroxyisocaproate	ChEBI
3-Hydroxy-4-methyl-3-carboxypentanoate	ChEBI
alpha-Isopropylmalate	ChEBI
2-Hydroxy-2-isopropylsuccinic acid	Generator
3-Carboxy-3-hydroxy-4-methylpentanoic acid	Generator
3-Carboxy-3-hydroxyisocaproic acid	Generator
3-Hydroxy-4-methyl-3-carboxypentanoic acid	Generator
a-Isopropylmalate	Generator
a-Isopropylmalic acid	Generator
alpha-Isopropylmalic acid	Generator
Α-isopropylmalate	Generator
Α-isopropylmalic acid	Generator
3-Carboxy-3-hydroxy-isocaproic acid	Generator

Chemical Formula

C₇H₁₀O₅

Average Molecular Weight

174.1513

Monoisotopic Molecular Weight

174.05282343

IUPAC Name

2-hydroxy-2-(propan-2-yl)butanedioate

Traditional Name

2-isopropylmalate

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)/p-2

InChI Key

BITYXLXUCSKTJS-UHFFFAOYSA-L

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
Dicarboxylic acid or derivatives
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid dianion (CHEBI:28107 )
a small molecule (3-CARBOXY-3-HYDROXY-ISOCAPROATE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	41.3 g/L	ALOGPS
logP	-0.1	ALOGPS
logP	0.21	ChemAxon
logS	-0.71	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	1	ChemAxon
Polar Surface Area	100.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	60.26 m³·mol⁻¹	ChemAxon
Polarizability	15.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-05d12fb256c35fe44030	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ow-8900000000-87fc335f95e2e5d7706c	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xr-7900000000-6d742aea834098a47a78	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-4900000000-572b60751e5d80bdeafb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0019-9600000000-bff27fb29bfce1df6dbe	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9100000000-438c2f1f71f400371db5	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

3-CARBOXY-3-HYDROXY-ISOCAPROATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28107

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Howell DM, Graupner M, Xu H, White RH: Identification of enzymes homologous to isocitrate dehydrogenase that are involved in coenzyme B and leucine biosynthesis in methanoarchaea. J Bacteriol. 2000 Sep;182(17):5013-6. doi: 10.1128/JB.182.17.5013-5016.2000. [PubMed:10940051 ]
van der Werf MJ, Overkamp KM, Muilwijk B, Coulier L, Hankemeier T: Microbial metabolomics: toward a platform with full metabolome coverage. Anal Biochem. 2007 Nov 1;370(1):17-25. doi: 10.1016/j.ab.2007.07.022. Epub 2007 Aug 1. [PubMed:17765195 ]
Keseler IM, Collado-Vides J, Santos-Zavaleta A, Peralta-Gil M, Gama-Castro S, Muniz-Rascado L, Bonavides-Martinez C, Paley S, Krummenacker M, Altman T, Kaipa P, Spaulding A, Pacheco J, Latendresse M, Fulcher C, Sarker M, Shearer AG, Mackie A, Paulsen I, Gunsalus RP, Karp PD: EcoCyc: a comprehensive database of Escherichia coli biology. Nucleic Acids Res. 2011 Jan;39(Database issue):D583-90. doi: 10.1093/nar/gkq1143. Epub 2010 Nov 21. [PubMed:21097882 ]
Kanehisa M, Goto S, Sato Y, Furumichi M, Tanabe M: KEGG for integration and interpretation of large-scale molecular data sets. Nucleic Acids Res. 2012 Jan;40(Database issue):D109-14. doi: 10.1093/nar/gkr988. Epub 2011 Nov 10. [PubMed:22080510 ]

Showing metabocard for 3-Carboxy-3-hydroxy-isocaproate (MMDBc0029761)

MOL for #<Metabolite:0x000055b76e230f20>

3D MOL for #<Metabolite:0x000055b76e230f20>

3D SDF for #<Metabolite:0x000055b76e230f20>

3D-SDF for #<Metabolite:0x000055b76e230f20>

PDB for #<Metabolite:0x000055b76e230f20>

3D PDB for #<Metabolite:0x000055b76e230f20>

SMILES for #<Metabolite:0x000055b76e230f20>

INCHI for #<Metabolite:0x000055b76e230f20>

Structure for #<Metabolite:0x000055b76e230f20>

3D Structure for #<Metabolite:0x000055b76e230f20>