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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:30 UTC

Update Date

2023-02-21 17:18:53 UTC

HMDB ID

HMDB0029616

Secondary Accession Numbers

HMDB29616

Metabolite Identification

Common Name

Diazenedicarboxamide

Description

Diazenedicarboxamide belongs to the class of organic compounds known as azo compounds. These are derivatives of diazene(diimide), HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPh azobenzene or diphenyldiazene. Diazenedicarboxamide is an odorless tasting compound. Based on a literature review a small amount of articles have been published on Diazenedicarboxamide.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,1'-Azobiscarbamide	HMDB
1,1'-Azobis[formamide]	HMDB
1,1'-Azodiformamide	HMDB
AZM 2S	HMDB
Azobis ca 110b	HMDB
Azobis ca 51C	HMDB
Azobiscarbonamide	HMDB
Azobiscarboxamide	HMDB
Azobisformamide	HMDB
Azocel	HMDB
Azodicarbamide	HMDB
Azodicarboamide	HMDB
Azodicarbonamide	HMDB
Azodicarboxamide	HMDB
Azodicarboxylic acid diamide	HMDB
Azodiformamide	HMDB
Azoform a	HMDB
Azoformamide	HMDB
Azoplastone	HMDB
Celogen az	HMDB
Evipor	HMDB
Genitron epc	HMDB
Paramid K1	HMDB
Vinyfor	HMDB
1,1-Azobisformamide	MeSH, HMDB
(e)-N-[(C-Hydroxycarbonimidoyl)imino]carbamimidate	Generator

Chemical Formula

C₂H₄N₄O₂

Average Molecular Weight

116.0788

Monoisotopic Molecular Weight

116.033425392

IUPAC Name

(E)-N-[(C-hydroxycarbonimidoyl)imino]carbamimidic acid

Traditional Name

azodicarbonamide

CAS Registry Number

123-77-3

SMILES

OC(=N)\N=N\C(O)=N

InChI Identifier

InChI=1S/C2H4N4O2/c3-1(7)5-6-2(4)8/h(H2,3,7)(H2,4,8)/b6-5+

InChI Key

XOZUGNYVDXMRKW-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azo compounds. These are derivatives of diazene(diimide), HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.G. PhN=NPh azobenzene or diphenyldiazene.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Azo compounds

Direct Parent

Azo compounds

Alternative Parents

Substituents

Azo compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Respiratory system disorder

Rhinitis (HMDB: HMDB0029616)

Observation

Cough (HMDB: HMDB0029616)

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029616)
Cytoplasm (HMDB: HMDB0029616)

Route of exposure

Parenteral

Enteral

Ingestion (HMDB: HMDB0029616)

Source

Exogenous

Exogenous (HMDB: HMDB0029616)

Food

Food (HMDB: HMDB0029616)

Process

Not Available

Role

Industrial application

Food and nutrition

Food and nutrition (HMDB: HMDB0029616)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	225 °C	Not Available
Boiling Point	284.78 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.035 mg/mL at 20 °C	Not Available
LogP	-1.70	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.93 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.51	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.04	ChemAxon
pKa (Strongest Basic)	1.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.88 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.36 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	122.791	30932474
DeepCCS	[M-H]-	120.665	30932474
DeepCCS	[M-2H]-	156.996	30932474
DeepCCS	[M+Na]+	131.655	30932474
AllCCS	[M+H]+	129.7	32859911
AllCCS	[M+H-H2O]+	125.6	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	121.6	32859911
AllCCS	[M+Na-2H]-	125.0	32859911
AllCCS	[M+HCOO]-	128.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	-0.55 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3444 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.56 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	161.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	922.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	363.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	65.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	249.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	277.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	330.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	451.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	616.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	58.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	880.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	216.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	688.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	244.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	278.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diazenedicarboxamide	OC(=N)\N=N\C(O)=N	2238.1	Standard polar	33892256
Diazenedicarboxamide	OC(=N)\N=N\C(O)=N	1831.9	Standard non polar	33892256
Diazenedicarboxamide	OC(=N)\N=N\C(O)=N	1644.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diazenedicarboxamide,1TMS,isomer #1	C[Si](C)(C)OC(=N)/N=N/C(=N)O	1708.8	Semi standard non polar	33892256
Diazenedicarboxamide,1TMS,isomer #2	C[Si](C)(C)N=C(O)/N=N/C(=N)O	1705.0	Semi standard non polar	33892256
Diazenedicarboxamide,2TMS,isomer #1	C[Si](C)(C)OC(=N)/N=N/C(=N)O[Si](C)(C)C	1669.1	Semi standard non polar	33892256
Diazenedicarboxamide,2TMS,isomer #2	C[Si](C)(C)N=C(/N=N/C(=N)O)O[Si](C)(C)C	1579.2	Semi standard non polar	33892256
Diazenedicarboxamide,2TMS,isomer #3	C[Si](C)(C)N=C(O)/N=N/C(=N)O[Si](C)(C)C	1662.5	Semi standard non polar	33892256
Diazenedicarboxamide,2TMS,isomer #4	C[Si](C)(C)N=C(O)/N=N/C(O)=N[Si](C)(C)C	1689.6	Semi standard non polar	33892256
Diazenedicarboxamide,3TMS,isomer #1	C[Si](C)(C)N=C(/N=N/C(=N)O[Si](C)(C)C)O[Si](C)(C)C	1610.8	Semi standard non polar	33892256
Diazenedicarboxamide,3TMS,isomer #1	C[Si](C)(C)N=C(/N=N/C(=N)O[Si](C)(C)C)O[Si](C)(C)C	1528.5	Standard non polar	33892256
Diazenedicarboxamide,3TMS,isomer #2	C[Si](C)(C)N=C(O)/N=N/C(=N[Si](C)(C)C)O[Si](C)(C)C	1595.2	Semi standard non polar	33892256
Diazenedicarboxamide,3TMS,isomer #2	C[Si](C)(C)N=C(O)/N=N/C(=N[Si](C)(C)C)O[Si](C)(C)C	1587.5	Standard non polar	33892256
Diazenedicarboxamide,4TMS,isomer #1	C[Si](C)(C)N=C(/N=N/C(=N[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1602.4	Semi standard non polar	33892256
Diazenedicarboxamide,4TMS,isomer #1	C[Si](C)(C)N=C(/N=N/C(=N[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1533.1	Standard non polar	33892256
Diazenedicarboxamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)/N=N/C(=N)O	1811.0	Semi standard non polar	33892256
Diazenedicarboxamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(O)/N=N/C(=N)O	1829.5	Semi standard non polar	33892256
Diazenedicarboxamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)/N=N/C(=N)O[Si](C)(C)C(C)(C)C	1990.5	Semi standard non polar	33892256
Diazenedicarboxamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(/N=N/C(=N)O)O[Si](C)(C)C(C)(C)C	1966.0	Semi standard non polar	33892256
Diazenedicarboxamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(O)/N=N/C(=N)O[Si](C)(C)C(C)(C)C	1999.3	Semi standard non polar	33892256
Diazenedicarboxamide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(O)/N=N/C(O)=N[Si](C)(C)C(C)(C)C	2049.7	Semi standard non polar	33892256
Diazenedicarboxamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(/N=N/C(=N)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2107.2	Semi standard non polar	33892256
Diazenedicarboxamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(/N=N/C(=N)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2060.3	Standard non polar	33892256
Diazenedicarboxamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(O)/N=N/C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2147.2	Semi standard non polar	33892256
Diazenedicarboxamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(O)/N=N/C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2036.8	Standard non polar	33892256
Diazenedicarboxamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(/N=N/C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2284.0	Semi standard non polar	33892256
Diazenedicarboxamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(/N=N/C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2167.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diazenedicarboxamide EI-B (Non-derivatized)	splash10-0006-9000000000-d9507c6601ed8a1597f5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diazenedicarboxamide EI-B (Non-derivatized)	splash10-0006-9000000000-d9507c6601ed8a1597f5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diazenedicarboxamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-c307f8e6893df84fd2ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diazenedicarboxamide GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-4900000000-232f2521a6984367eb01	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diazenedicarboxamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Diazenedicarboxamide 10V, Positive-QTOF	splash10-00xr-9600000000-911e5d6523695f11747d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 20V, Positive-QTOF	splash10-00di-9200000000-05b9dcc86a3c5daa2825	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 40V, Positive-QTOF	splash10-0a4i-9000000000-1ccba6e08aa707e5f9d6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 10V, Negative-QTOF	splash10-00xr-9400000000-94d273da4c163d9188ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 20V, Negative-QTOF	splash10-0fk9-9000000000-f5939e858def38d57aa3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 40V, Negative-QTOF	splash10-0006-9000000000-25ff1dc3f963a249f5d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 10V, Negative-QTOF	splash10-0006-9200000000-723f50b9a3b4f67ac2c0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 20V, Negative-QTOF	splash10-0006-9000000000-f2a1ebbed095f8bd6988	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 10V, Positive-QTOF	splash10-014l-7900000000-04389a0e6ed5af1cd5ba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 20V, Positive-QTOF	splash10-0006-9000000000-e0c6e70e64689ecbab86	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diazenedicarboxamide 40V, Positive-QTOF	splash10-052f-9000000000-c04342d4a4666f27eb47	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB000784

KNApSAcK ID

Not Available

Chemspider ID

4575589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azodicarbonamide

METLIN ID

Not Available

PubChem Compound

5462814

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1040011

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Diazenedicarboxamide (HMDB0029616)

MOL for HMDB0029616 (Diazenedicarboxamide)

3D MOL for HMDB0029616 (Diazenedicarboxamide)

3D SDF for HMDB0029616 (Diazenedicarboxamide)

3D-SDF for HMDB0029616 (Diazenedicarboxamide)

PDB for HMDB0029616 (Diazenedicarboxamide)

3D PDB for HMDB0029616 (Diazenedicarboxamide)

SMILES for HMDB0029616 (Diazenedicarboxamide)

INCHI for HMDB0029616 (Diazenedicarboxamide)

Structure for HMDB0029616 (Diazenedicarboxamide)

3D Structure for HMDB0029616 (Diazenedicarboxamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra