MiMeDB: Showing metabocard for 3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate (MMDBc0033001)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:30:37 UTC

Update Date

2022-08-31 21:55:30 UTC

Metabolite ID

MMDBc0033001

Metabolite Identification

Common Name

3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate

Description

3-Hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate is a methyl ester of (2R,3S)-3-isopropylmalate formed by the methylation of this compound through trans-aconitate methyltransferase. It is found in the cytosol and may spontaneously demethylate to form an acid. The specific function of this compound in the yeast cell is unknown.

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.310  -4.001   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.620  -2.667   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.850  -6.668   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.160  -5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.930  -6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.470  -6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.160  -8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.470  -4.001   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
3-Hydroxy-2-isopropyl-4-methoxy-4-oxobutanoic acid	Generator

Molecular Formula

C₈H₁₄O₅

Average Mass

190.1938

Monoisotopic Mass

190.084123558

IUPAC Name

3-hydroxy-4-methoxy-4-oxo-2-(propan-2-yl)butanoic acid

Traditional Name

3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C(O)C(C(C)C)C(O)=O

InChI Identifier

InChI=1S/C8H14O5/c1-4(2)5(7(10)11)6(9)8(12)13-3/h4-6,9H,1-3H3,(H,10,11)

InChI Key

YFUPBIBIDVFELV-UHFFFAOYSA-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

Beta-hydroxy acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acid ester
Short-chain hydroxy acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Hydroxy acid
Methyl ester
Secondary alcohol
Carboxylic acid ester
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

dicarboxylic acid monoester (CHEBI:52978 )
methyl ester (CHEBI:52978 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	72.8 g/L	ALOGPS
logP	0.35	ALOGPS
logP	0.31	ChemAxon
logS	-0.42	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	43.37 m³·mol⁻¹	ChemAxon
Polarizability	18.56 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-ba4ea1576bf19b444ad0	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1900000000-3b008c05d8d347c7a34e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-7900000000-b609dc24900b3d497a71	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052u-9300000000-74560da815ec333a3414	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-aac7a4644a06f5badfff	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pbi-7900000000-ffd6acb5c15109f56640	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9200000000-fd286b84b14a007b32c8	2016-09-12	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	247.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	99.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	314.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	377.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	318.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	299.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1294.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	122.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	624.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	228.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	238.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	169.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	88.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	161.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	390.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	51.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	261.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1041.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	702.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate_TMS_1	COC(=O)C(O[Si](C)(C)C)C(C(=O)O)C(C)C	standard non polar	2025-10-24	2096.75
Gas Chromatography	3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate_TMS_2	COC(=O)C(O)C(C(=O)O[Si](C)(C)C)C(C)C	standard non polar	2025-10-24	2120.23
Gas Chromatography	3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate_TMS_3	COC(=O)C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C(C)C	standard non polar	2025-10-24	2050.58
Gas Chromatography	3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate_TMS_1	COC(=O)C(O[Si](C)(C)C)C(C(=O)O)C(C)C	standard polar	2025-10-24	2067.8
Gas Chromatography	3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate_TMS_2	COC(=O)C(O)C(C(=O)O[Si](C)(C)C)C(C)C	standard polar	2025-10-24	2344.65
Gas Chromatography	3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate_TMS_3	COC(=O)C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)C(C)C	standard polar	2025-10-24	2412.17

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44176396

PDB ID

Not Available

ChEBI ID

52978

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Katz JE, Dumlao DS, Wasserman JI, Lansdown MG, Jung ME, Faull KF, Clarke S: 3-Isopropylmalate is the major endogenous substrate of the Saccharomyces cerevisiae trans-aconitate methyltransferase. Biochemistry. 2004 May 25;43(20):5976-86. doi: 10.1021/bi049784+. [PubMed:15147181 ]
Herrgard MJ, Swainston N, Dobson P, Dunn WB, Arga KY, Arvas M, Bluthgen N, Borger S, Costenoble R, Heinemann M, Hucka M, Le Novere N, Li P, Liebermeister W, Mo ML, Oliveira AP, Petranovic D, Pettifer S, Simeonidis E, Smallbone K, Spasic I, Weichart D, Brent R, Broomhead DS, Westerhoff HV, Kirdar B, Penttila M, Klipp E, Palsson BO, Sauer U, Oliver SG, Mendes P, Nielsen J, Kell DB: A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology. Nat Biotechnol. 2008 Oct;26(10):1155-60. doi: 10.1038/nbt1492. [PubMed:18846089 ]

Showing metabocard for 3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoate (MMDBc0033001)

MOL for #<Metabolite:0x00007f9acf196c40>

3D MOL for #<Metabolite:0x00007f9acf196c40>

3D SDF for #<Metabolite:0x00007f9acf196c40>

3D-SDF for #<Metabolite:0x00007f9acf196c40>

PDB for #<Metabolite:0x00007f9acf196c40>

3D PDB for #<Metabolite:0x00007f9acf196c40>

SMILES for #<Metabolite:0x00007f9acf196c40>

INCHI for #<Metabolite:0x00007f9acf196c40>

Structure for #<Metabolite:0x00007f9acf196c40>

3D Structure for #<Metabolite:0x00007f9acf196c40>