MiMeDB: Showing metabocard for Maleamate (MMDBc0000742)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:53:59 UTC

Update Date

2025-10-07 16:04:14 UTC

Metabolite ID

MMDBc0000742

Metabolite Identification

Common Name

Maleamate

Description

Maleamate is a metabolite classified within the category of amino acid derivatives. Its chemical structure features a maleic acid backbone, which is modified by the addition of an amine group, resulting in unique reactivity profiles. Maleamate plays a role in various biochemical pathways, including its involvement in the inhibition of fungal growth, as demonstrated by its ability to inhibit the growth of A. (PMID:38671402 ). Additionally, it has been utilized in bioconjugation techniques, specifically in the development of a maleamate-based prosthetic group for efficient, site-specific radioiodination of proteins and antibodies containing cysteine residues (PMID:38746876 ). Furthermore, maleamate is part of supramolecular structures, such as sodium N-(dehydroabietyl)maleamate/Ca2+ metallohydrogels, which exhibit multi-stimulus responsiveness to various environmental factors, showcasing its versatility in material science (PMID:37348017 ). Notably, maleamate levels have been positively correlated with the number of retrieved oocytes in patients undergoing ovarian hyperstimulation syndrome (OHSS), indicating its potential relevance in reproductive biology (PMID:36967756 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Maleamic acid	Generator

Molecular Formula

C₄H₄NO₃

Average Mass

114.081

Monoisotopic Mass

114.019666573

IUPAC Name

(2Z)-3-carboxyprop-2-enecarboximidate

Traditional Name

(2Z)-3-carboxyprop-2-enecarboximidate

CAS Registry Number

Not Available

SMILES

OC(=O)\C=C/C([O-])=N

InChI Identifier

InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)/p-1/b2-1-

InChI Key

FSQQTNAZHBEJLS-UPHRSURJSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

Substituents

Straight chain fatty acid
Unsaturated fatty acid
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid anion (CHEBI:16146 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.18 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	-2.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	-0.25	ChemAxon
pKa (Strongest Basic)	12.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.92 m³·mol⁻¹	ChemAxon
Polarizability	9.48 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	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	View 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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank
Nicotine degradation, pyrrolidine pathway

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
Bacteria/Eubacteria	Firmicutes	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Proteobacteria	1

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

HMDB0240339

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00053453

Chemspider ID

4573932

KEGG Compound ID

Not Available

BioCyc ID

MALEAMATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5460391

PDB ID

Not Available

ChEBI ID

16146

CMMC Knowledgebase

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Maleamate (MMDBc0000742)

MOL for #<Metabolite:0x00007fd4490cd210>

3D MOL for #<Metabolite:0x00007fd4490cd210>

3D SDF for #<Metabolite:0x00007fd4490cd210>

3D-SDF for #<Metabolite:0x00007fd4490cd210>

PDB for #<Metabolite:0x00007fd4490cd210>

3D PDB for #<Metabolite:0x00007fd4490cd210>

SMILES for #<Metabolite:0x00007fd4490cd210>

INCHI for #<Metabolite:0x00007fd4490cd210>

Structure for #<Metabolite:0x00007fd4490cd210>

3D Structure for #<Metabolite:0x00007fd4490cd210>