2-Isopropylmaleate (BioCAD00000002614)
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Metabolite Card
Formula: C7H10O4 (158.0579)
SMILES: CC(C)C(=C\C(O)=O)\C(O)=O
Synonyms [en]
2-isopropylmaleate; beta-Isopropylmaleate; 2-isopropylmaleic acid; (2Z)-2-(propan-2-yl)but-2-enedioic acid; b-isopropylmaleate; isopropylmaleate
Last reviewed on 2024-06-28.
Cite this Page
2-Isopropylmaleate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000002614). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
2-Isopropylmaleic acid belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually they are saturated and contain one or more methyl groups. However, branches other than methyl groups may be present. 2-Isopropylmaleic acid is a moderately acidic compound (based on its pKa). Isopropylmaleic acid is found in the leucine biosynthesis pathway. It is synthesized from oxoisovalerate by 2-isopropylmalate synthase and converted into isopropyl-3-oxosuccinate by 3-isopropylmalate dehydrogenase. The 2- and 3-isopropyl derivatives of isopropylmaleic acid are interconverted by the enzyme isopropylmalate dehydratase.
DBLinks
- CAS Registry Number: 44976-69-4
- PubChem CID: 5280533
- ChEBI: 17275
- HMDB: HMDB0012241
- LipidMaps:
- KEGG: C02631
- BioCyc:
- NCBI MeSH:
- Wikipedia: Isopropylmalic_acid
Other DBLinks
- CAS Registry Number: 44976-69-4
- CAS Registry Number: 7596-39-6
- PubChem: 5280533
- ChEBI: ChEBI:17275
- HMDB: HMDB0012241
- KEGG: C02631
- Wikipedia: Isopropylmalic_acid
- RefMet: RM0153294
- Metlin: METLIN_3279
- Coconut NaturalProduct: CNP0194846.0
Class / Ontology
- WishartLab ClassyFire: [Fatty acids and conjugates] Fatty acids and conjugates
- RefMet: [Dicarboxylic acids] Dicarboxylic acids
- ChEBI: [CHEBI:17275] 2-isopropylmaleic acid
- Coconut NaturalProduct: [Branched fatty acids] Branched fatty acids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R03968 | 4.2.1.33 | 2-isopropylmalate hydro-lyase |
| KEGG:R04001 | 4.2.1.33 | 3-isopropylmalate hydro-lyase |
Taxonomy Source
- Citrullus lanatus [ncbi taxid: 3654]
- Escherichia coli [ncbi taxid: 562]
- Saccharomyces cerevisiae [ncbi taxid: 4932]
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:CAULONA1000_BRANCHED-CHAIN-AA-SYN-PWY | superpathway of leucine, valine, and isoleucine biosynthesis |
| BioCyc:CAULONA1000_LEUSYN-PWY | leucine biosynthesis |
| PathBank:SMP0000831 | Leucine Biosynthesis |
| PathBank:SMP0000994 | Secondary Metabolites: Valine and L-Leucine Biosynthesis from Pyruvate |
| PathBank:SMP0000996 | Secondary Metabolites: Leucine Biosynthesis |
| PathBank:SMP0121332 | Secondary Metabolites: Leucine Biosynthesis |
| PathBank:SMP0121287 | Leucine Biosynthesis |
| PathBank:SMP0121331 | Secondary Metabolites: Valine and L-Leucine Biosynthesis from Pyruvate |
| PathBank:SMP0002432 | Leucine Biosynthesis |
| PathBank:SMP0002374 | Leucine Biosynthesis |