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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:32:49 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254314

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Malonamide

Description

malonamide, also known as malonic diimidate, belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group. Based on a literature review a significant number of articles have been published on malonamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Malonamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Malonamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Carboxamidoacetamide	ChEBI
Malondiamide	ChEBI
Malonic acid diamide	ChEBI
Malonic diamide	ChEBI
Malonodiamide	ChEBI
Malonyldiamide	ChEBI
Methane-1,1-dicarboxamide	ChEBI
Malonate diamide	Generator
Malonic diimidate	MeSH
Propanediimidate	Generator

Chemical Formula

C₃H₆N₂O₂

Average Molecular Weight

102.0919

Monoisotopic Molecular Weight

102.042927446

IUPAC Name

propanediimidic acid

Traditional Name

propanediimidic acid

CAS Registry Number

Not Available

SMILES

OC(=N)CC(O)=N

InChI Identifier

InChI=1S/C3H6N2O2/c4-2(6)1-3(5)7/h1H2,(H2,4,6)(H2,5,7)

InChI Key

WRIRWRKPLXCTFD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

1,3-dicarbonyl compounds

Alternative Parents

Substituents

1,3-dicarbonyl compound
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.5	ALOGPS
logP	-5.6	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	-2.7	ChemAxon
pKa (Strongest Basic)	13.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	88.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.51 m³·mol⁻¹	ChemAxon
Polarizability	8.83 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	125.629	30932474
DeepCCS	[M-H]-	123.637	30932474
DeepCCS	[M-2H]-	159.532	30932474
DeepCCS	[M+Na]+	134.17	30932474
AllCCS	[M+H]+	125.6	32859911
AllCCS	[M+H-H2O]+	121.2	32859911
AllCCS	[M+NH4]+	129.6	32859911
AllCCS	[M+Na]+	130.7	32859911
AllCCS	[M-H]-	120.4	32859911
AllCCS	[M+Na-2H]-	124.3	32859911
AllCCS	[M+HCOO]-	128.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
MALONAMIDE	OC(=N)CC(O)=N	2388.7	Standard polar	33892256
MALONAMIDE	OC(=N)CC(O)=N	1385.2	Standard non polar	33892256
MALONAMIDE	OC(=N)CC(O)=N	1467.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
MALONAMIDE,3TMS,isomer #1	C[Si](C)(C)N=C(CC(=N)O[Si](C)(C)C)O[Si](C)(C)C	1520.1	Semi standard non polar	33892256
MALONAMIDE,3TMS,isomer #1	C[Si](C)(C)N=C(CC(=N)O[Si](C)(C)C)O[Si](C)(C)C	1477.1	Standard non polar	33892256
MALONAMIDE,3TMS,isomer #1	C[Si](C)(C)N=C(CC(=N)O[Si](C)(C)C)O[Si](C)(C)C	1782.6	Standard polar	33892256
MALONAMIDE,3TMS,isomer #2	C[Si](C)(C)N=C(O)CC(=N[Si](C)(C)C)O[Si](C)(C)C	1539.6	Semi standard non polar	33892256
MALONAMIDE,3TMS,isomer #2	C[Si](C)(C)N=C(O)CC(=N[Si](C)(C)C)O[Si](C)(C)C	1462.2	Standard non polar	33892256
MALONAMIDE,3TMS,isomer #2	C[Si](C)(C)N=C(O)CC(=N[Si](C)(C)C)O[Si](C)(C)C	1889.5	Standard polar	33892256
MALONAMIDE,4TMS,isomer #1	C[Si](C)(C)N=C(CC(=N[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1554.1	Semi standard non polar	33892256
MALONAMIDE,4TMS,isomer #1	C[Si](C)(C)N=C(CC(=N[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1513.7	Standard non polar	33892256
MALONAMIDE,4TMS,isomer #1	C[Si](C)(C)N=C(CC(=N[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1629.3	Standard polar	33892256
MALONAMIDE,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=N)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2130.4	Semi standard non polar	33892256
MALONAMIDE,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=N)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2037.1	Standard non polar	33892256
MALONAMIDE,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=N)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2088.9	Standard polar	33892256
MALONAMIDE,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(O)CC(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2096.4	Semi standard non polar	33892256
MALONAMIDE,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(O)CC(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1966.2	Standard non polar	33892256
MALONAMIDE,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(O)CC(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2147.3	Standard polar	33892256
MALONAMIDE,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2299.2	Semi standard non polar	33892256
MALONAMIDE,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2154.3	Standard non polar	33892256
MALONAMIDE,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2106.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Malonamide GC-MS (2 TMS)	splash10-0159-3910000000-49ae8f5e55f5d3c84dd8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9300000000-14f7f7f94f25e354603a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Malonamide GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 10V, Positive-QTOF	splash10-0udr-7900000000-6784b20a8f7624d90fd3	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 20V, Positive-QTOF	splash10-00kr-9100000000-59338a2316f0f9330dff	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 40V, Positive-QTOF	splash10-000f-9000000000-f46bb8e51caab7433c81	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 10V, Negative-QTOF	splash10-0udi-3900000000-18f36e55f6fa43ad66d2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 20V, Negative-QTOF	splash10-0f6x-9400000000-2af42ce1568f9a3e4cf0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 40V, Negative-QTOF	splash10-0006-9000000000-f483bf546d1a4386196f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 10V, Positive-QTOF	splash10-0f76-9300000000-884220452a1304f4f2f4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 20V, Positive-QTOF	splash10-0006-9000000000-ecf9c6a6fcbc4bd40caa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 40V, Positive-QTOF	splash10-0006-9000000000-713dd9eabf888203832b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 10V, Negative-QTOF	splash10-0udi-4900000000-f30f0c6ccad50a08becb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 20V, Negative-QTOF	splash10-0pbc-9400000000-41513a9cfd5c2bd0dc0e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Malonamide 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7911

PDB ID

Not Available

ChEBI ID

48537

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Malonamide (HMDB0254314)

MOL for HMDB0254314 (Malonamide)

3D MOL for HMDB0254314 (Malonamide)

3D SDF for HMDB0254314 (Malonamide)

3D-SDF for HMDB0254314 (Malonamide)

PDB for HMDB0254314 (Malonamide)

3D PDB for HMDB0254314 (Malonamide)

SMILES for HMDB0254314 (Malonamide)

INCHI for HMDB0254314 (Malonamide)

Structure for HMDB0254314 (Malonamide)

3D Structure for HMDB0254314 (Malonamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra