MiMeDB: Showing metabocard for 3-Carboxy-4-methyl-2-oxopentanoate (MMDBc0049885)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:32 UTC

Update Date

2024-04-30 20:39:53 UTC

Metabolite ID

MMDBc0049885

Metabolite Identification

Common Name

3-Carboxy-4-methyl-2-oxopentanoate

Description

2-Isopropyl-3-oxosuccinate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Isopropyl-3-oxosuccinate exists in all living species, ranging from bacteria to plants to humans. 2-Isopropyl-3-oxosuccinate has been detected, but not quantified in, several different foods, such as chinese cinnamons (Cinnamomum aromaticum), rye bread, common sages (Salvia officinalis), olives (Olea europaea), and red raspberries (Rubus idaeus). This could make 2-isopropyl-3-oxosuccinate a potential biomarker for the consumption of these foods. 2-Isopropyl-3-oxosuccinate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 2-Isopropyl-3-oxosuccinate.

Structure

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

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.458   0.353   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.792  -0.417   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -1.458   1.893   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.124  -0.417   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.124  -1.957   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.209   0.353   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.209   1.893   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.124   2.663   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.543   2.663   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.543  -0.417   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.543  -1.957   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.877   0.353   0.000  0.00  0.00           C+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
(2S)-2-(1-Methylethyl)-3-oxobutanedioic acid	ChEBI
(2S)-2-Isopropyl-3-oxosuccinate	ChEBI
3-Carboxy-4-methyl-2-oxopentanoate	ChEBI
2-oxo-4-Methyl-3-carboxypentanoate	Kegg
(2S)-2-(1-Methylethyl)-3-oxobutanedioate	Generator
(2S)-2-Isopropyl-3-oxosuccinic acid	Generator
3-Carboxy-4-methyl-2-oxopentanoic acid	Generator
2-oxo-4-Methyl-3-carboxypentanoic acid	Generator
2-Isopropyl-3-oxosuccinic acid	Generator
(2S)-3-oxo-2-(Propan-2-yl)butanedioate	HMDB
(2S)-3-oxo-2-(Propan-2-yl)butanedioic acid	HMDB
2-(1-Methylethyl)-3-oxobutanedioic acid	HMDB
2-Oxo-3-isopropylsuccinic acid	HMDB

Molecular Formula

C₇H₁₀O₅

Average Mass

174.1513

Monoisotopic Mass

174.05282343

IUPAC Name

(3S)-2-oxo-3-(propan-2-yl)butanedioic acid

Traditional Name

(2S)-2-isopropyl-3-oxobutanedioic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](C(O)=O)C(=O)C(O)=O

InChI Identifier

InChI=1S/C7H10O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-4H,1-2H3,(H,9,10)(H,11,12)/t4-/m0/s1

InChI Key

HIIZAGQWABAMRR-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Beta-keto acid
Branched fatty acid
Short-chain keto acid
Methyl-branched fatty acid
Alpha-keto acid
Beta-hydroxy ketone
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Fatty acyl
Alpha-hydroxy ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo dicarboxylic acid (CHEBI:1467 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.02 g/L	ALOGPS
logP	0.43	ALOGPS
logP	1.23	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	-10	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.06 m³·mol⁻¹	ChemAxon
Polarizability	15.83 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	splash10-0006-9600000000-a431ad34a78f0adc25af	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0g74-9331000000-f234980692c6ed06a94e	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-1900000000-acd1ea66574d55eb331d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06v0-5900000000-7e737232c4fb38bff3bf	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9600000000-844c8da366f084302d2b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-1900000000-bdd65fc36b7ec2c68915	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-7900000000-31ff420a87e647dd1154	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9100000000-ffbf76307b5afc43379b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-2900000000-dea633070d58aa2d4298	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ar-9800000000-562cf1d81cbf0e6dfda1	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-27319b151cd6c10b30ce	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06ui-4900000000-5bcfc8907d6248e32900	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-f03654c5ee61af92206e	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-47f8865805b71fe90ddd	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007074	3-Carboxy-2-hydroxy-4-methylpentanoate	3-Carboxy-4-methyl-2-oxopentanoate	Not Available		VMH	30371894
MMDBr0008123	3-Carboxy-4-methyl-2-oxopentanoate	Ketoleucine	Not Available		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	313	Human feces; Human pleural fluid plaque; Pig ; Human ; Human supragingival plaque; Human saliva; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	175	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 pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	92	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	14	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	4		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	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0012149

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028806

KNApSAcK ID

Not Available

Chemspider ID

4575347

KEGG Compound ID

C04236

BioCyc ID

CPD-7100

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5462259

PDB ID

Not Available

ChEBI ID

1467

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 3-Carboxy-4-methyl-2-oxopentanoate (MMDBc0049885)

MOL for #<Metabolite:0x00007fed14dd1798>

3D MOL for #<Metabolite:0x00007fed14dd1798>

3D SDF for #<Metabolite:0x00007fed14dd1798>

3D-SDF for #<Metabolite:0x00007fed14dd1798>

PDB for #<Metabolite:0x00007fed14dd1798>

3D PDB for #<Metabolite:0x00007fed14dd1798>

SMILES for #<Metabolite:0x00007fed14dd1798>

INCHI for #<Metabolite:0x00007fed14dd1798>

Structure for #<Metabolite:0x00007fed14dd1798>

3D Structure for #<Metabolite:0x00007fed14dd1798>