MiMeDB: Showing metabocard for Maleamate (MMDBc0000742)

Record Information

Version

2.0

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

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)	2025-10-23	222.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	116.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	168.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (void)	2025-10-23	373.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	294.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	388.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1158.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	519.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	898.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	267.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	284.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	267.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	96.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	291.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	788.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	99.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	301.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1006.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	710.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Maleamate_TMS_1	C[Si](C)(C)OC(=O)/C=C\C(=N)[O-]	standard non polar	2025-10-23	1880.61
Gas Chromatography	Maleamate_TMS_2	C[Si](C)(C)N=C([O-])/C=C\C(=O)O	standard non polar	2025-10-23	2005.33
Gas Chromatography	Maleamate_TMS_3	C[Si](C)(C)N=C([O-])/C=C\C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2041.66
Gas Chromatography	Maleamate_TMS_1	C[Si](C)(C)OC(=O)/C=C\C(=N)[O-]	standard polar	2025-10-23	2062.76
Gas Chromatography	Maleamate_TMS_2	C[Si](C)(C)N=C([O-])/C=C\C(=O)O	standard polar	2025-10-23	2421.1
Gas Chromatography	Maleamate_TMS_3	C[Si](C)(C)N=C([O-])/C=C\C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1913.83

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

Name	SMPDB/PathBank	Species
Nicotine degradation, pyrrolidine pathway		Mycobacterium marinum M Bacillus cereus Saccharopolyspora erythraea NRRL 2338 Streptomyces avermitilis MA-4680 Bacillus cereus AH187 (F4810/72) Alkalihalobacillus pseudofirmus OF4 Brevibacillus brevis NBRC 100599 Eggerthella lenta DSM 2243 Methylobacterium nodulans Comamonas testosteroni Pseudomonas putida Bradyrhizobium japonicum Mesorhizobium loti Sinorhizobium meliloti Rhodopseudomonas palustris Bacillus mycoides Bacillus thuringiensis Bacillus pseudofirmus Achromobacter xylosoxidans Burkholderia multivorans Burkholderia cenocepacia Syntrophobacter fumaroxidans Burkholderia ambifaria Anaerotruncus colihominis Coprococcus comes Achromobacter xylosoxidans A8 Bacillus cereus ATCC 10987 Bacillus cereus AH820 Bacillus cereus G9842 Bacillus cereus Q1 Bradyrhizobium japonicum USDA 110 Delftia acidovorans SPH-1 Mesorhizobium loti MAFF303099 Methylobacterium radiotolerans JCM 2831 Methylobacterium populi BJ001 Pseudomonas putida KT2440 Pseudomonas fluorescens SBW25 Pseudomonas putida GB-1 Spirosoma linguale DSM 74 Spirosoma linguale Bradyrhizobium elkanii Rhizobium etli Alcaligenes faecalis Burkholderia cepacia GG4 Tatumella ptyseos ATCC 33301 Serratia marcescens subsp. marcescens Db11 Streptomyces avermitilis Bacillus firmus DS1 Aneurinibacillus aneurinilyticus Aneurinibacillus aneurinilyticus ATCC 12856 Enterococcus casseliflavus ATCC 12755 Coprococcus comes ATCC 27758 [Clostridium] symbiosum WAL-14163 Anaerotruncus colihominis DSM 17241 Streptomyces coelicolor A3(2) Bordetella pertussis Tohama I Bordetella parapertussis 12822 Ralstonia eutropha H16 Alkaliphilus metalliredigens QYMF Arthrobacter sp. FB24 Catenulispora acidiphila DSM 44928 Conexibacter woesei DSM 14684 Gordonia bronchialis DSM 43247 Mycobacterium vanbaalenii PYR-1 Mycobacterium abscessus ATCC 19977 Pseudonocardia dioxanivorans CB1190 Renibacterium salmoninarum ATCC 33209 Rhodococcus opacus B4 Rhodococcus jostii RHA1 Stackebrandtia nassauensis DSM 44728 Streptomyces violaceusniger Tu 4113 Streptosporangium roseum DSM 43021 Penicillium concentricum Fusarium equiseti Fusarium vanettenii Fusarium vanettenii 77-13-4 Acidovorax citrulli AAC00-1 Agrobacterium radiobacter K84 Anabaena variabilis ATCC 29413 Bordetella avium 197N Bradyrhizobium sp. ORS278 Bradyrhizobium sp. BTAi1 Burkholderia sp. 383 Burkholderia xenovorans LB400 Burkholderia cenocepacia MC0-3 Burkholderia phymatum STM815 Burkholderia cenocepacia J2315 Cellulophaga algicola DSM 14237 Chloroflexus aurantiacus J-10-fl Cupriavidus metallidurans CH34 Cupriavidus taiwanensis LMG 19424 Cupriavidus necator N-1 Desulfitobacterium hafniense Y51 Dickeya dadantii Ech703 Geobacter uraniireducens Rf4 Geobacter sp. FRC-32 Haliangium ochraceum DSM 14365 Legionella longbeachae NSW150 Methylobacterium chloromethanicum CM4 Methylobacterium nodulans ORS 2060 Nostoc sp. PCC 7120 Bordetella bronchiseptica RB50 Sorangium cellulosum 'So ce 56' Rhodobacter capsulatus SB1003 Paracoccus denitrificans PD1222 Pseudomonas syringae pv. tomato str. DC3000 Rhizobium etli CFN 42 Rhizobium etli CIAT 652 Rhizobium leguminosarum bv. trifolii WSM1325 Roseiflexus sp. RS-1 Roseiflexus castenholzii DSM 13941 Roseobacter litoralis Och 149 Ruegeria pomeroyi DSS-3 Sinorhizobium meliloti 1021 Sinorhizobium medicae WSM419 Sphingomonas wittichii RW1 Syntrophobacter fumaroxidans MPOB

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

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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:0x00007f9acdf55270>

3D MOL for #<Metabolite:0x00007f9acdf55270>

3D SDF for #<Metabolite:0x00007f9acdf55270>

3D-SDF for #<Metabolite:0x00007f9acdf55270>

PDB for #<Metabolite:0x00007f9acdf55270>

3D PDB for #<Metabolite:0x00007f9acdf55270>

SMILES for #<Metabolite:0x00007f9acdf55270>

INCHI for #<Metabolite:0x00007f9acdf55270>

Structure for #<Metabolite:0x00007f9acdf55270>

3D Structure for #<Metabolite:0x00007f9acdf55270>