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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:32:59 UTC

Update Date

2021-09-26 23:00:46 UTC

HMDB ID

HMDB0249720

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(3-Chlorophenyl)hydrazonomalononitrile

Description

Carbonyl cyanide m-chlorophenyl hydrazone, also known as (3-chlorophenyl)hydrazonomalononitrile, belongs to the class of organic compounds known as phenylhydrazines. Phenylhydrazines are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group. Based on a literature review a significant number of articles have been published on Carbonyl cyanide m-chlorophenyl hydrazone. This compound has been identified in human blood as reported by (PMID: 31557052 ). (3-chlorophenyl)hydrazonomalononitrile is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (3-Chlorophenyl)hydrazonomalononitrile 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

  Mrv0541 02241204102D          

 14 14  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  3  0  0  0  0
  9 12  1  0  0  0  0
 12 13  3  0  0  0  0
  6 14  2  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249720

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=CC(NN=C(C#N)C#N)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H

> <INCHI_KEY>
UGTJLJZQQFGTJD-UHFFFAOYSA-N

> <FORMULA>
C9H5ClN4

> <MOLECULAR_WEIGHT>
204.616

> <EXACT_MASS>
204.020273887

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.17412068790767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(3-chlorophenyl)-1-cyanomethanecarbohydrazonoyl cyanide

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
3.1936084326666663

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.596133924757995

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9773083044539317

> <JCHEM_POLAR_SURFACE_AREA>
71.97

> <JCHEM_REFRACTIVITY>
54.28570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
CCCP

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.001  -0.770   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.667   7.700   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.667   7.700   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12                                                            
CONECT   14    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3-Chlorophenyl)hydrazonomalononitrile	ChEBI
[(3-Chlorophenyl)hydrazono]malononitrile	ChEBI
[(3-Chlorophenyl)hydrazono]propanedinitrile	ChEBI
Carbonylcyanide-3-chlorophenylhydrazone	ChEBI
Carbonyl cyanide m chlorophenyl hydrazone	MeSH
Carbonyl cyanide meta chlorophenyl hydrazone	MeSH
Carbonyl cyanide meta-chlorophenyl hydrazone	MeSH

Chemical Formula

C₉H₅ClN₄

Average Molecular Weight

204.616

Monoisotopic Molecular Weight

204.020273887

IUPAC Name

N-(3-chlorophenyl)-1-cyanomethanecarbohydrazonoyl cyanide

Traditional Name

CCCP

CAS Registry Number

Not Available

SMILES

ClC1=CC=CC(NN=C(C#N)C#N)=C1

InChI Identifier

InChI=1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H

InChI Key

UGTJLJZQQFGTJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylhydrazines. Phenylhydrazines are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylhydrazines

Direct Parent

Phenylhydrazines

Alternative Parents

Substituents

Phenylhydrazine
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Nitrile
Carbonitrile
Hydrazone
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nitrile (CHEBI:3259 )
monochlorobenzenes (CHEBI:3259 )
hydrazone (CHEBI:3259 )
a small molecule (CPD-7970 )

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	3.3	ALOGPS
logP	3.19	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	10.6	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.29 m³·mol⁻¹	ChemAxon
Polarizability	19.17 Å³	ChemAxon
Number of Rings	1	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]+	139.954	30932474
DeepCCS	[M-H]-	137.558	30932474
DeepCCS	[M-2H]-	172.917	30932474
DeepCCS	[M+Na]+	148.272	30932474
AllCCS	[M+H]+	141.0	32859911
AllCCS	[M+H-H2O]+	137.1	32859911
AllCCS	[M+NH4]+	144.7	32859911
AllCCS	[M+Na]+	145.7	32859911
AllCCS	[M-H]-	139.1	32859911
AllCCS	[M+Na-2H]-	139.5	32859911
AllCCS	[M+HCOO]-	140.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3-Chlorophenyl)hydrazonomalononitrile	ClC1=CC=CC(NN=C(C#N)C#N)=C1	2733.1	Standard polar	33892256
(3-Chlorophenyl)hydrazonomalononitrile	ClC1=CC=CC(NN=C(C#N)C#N)=C1	1745.1	Standard non polar	33892256
(3-Chlorophenyl)hydrazonomalononitrile	ClC1=CC=CC(NN=C(C#N)C#N)=C1	2049.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3-Chlorophenyl)hydrazonomalononitrile,1TMS,isomer #1	C[Si](C)(C)N(N=C(C#N)C#N)C1=CC=CC(Cl)=C1	1967.8	Semi standard non polar	33892256
(3-Chlorophenyl)hydrazonomalononitrile,1TMS,isomer #1	C[Si](C)(C)N(N=C(C#N)C#N)C1=CC=CC(Cl)=C1	1796.0	Standard non polar	33892256
(3-Chlorophenyl)hydrazonomalononitrile,1TMS,isomer #1	C[Si](C)(C)N(N=C(C#N)C#N)C1=CC=CC(Cl)=C1	3861.6	Standard polar	33892256
(3-Chlorophenyl)hydrazonomalononitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C(C#N)C#N)C1=CC=CC(Cl)=C1	2154.0	Semi standard non polar	33892256
(3-Chlorophenyl)hydrazonomalononitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C(C#N)C#N)C1=CC=CC(Cl)=C1	2044.0	Standard non polar	33892256
(3-Chlorophenyl)hydrazonomalononitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C(C#N)C#N)C1=CC=CC(Cl)=C1	3851.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-3930000000-5f979150543fd51a00e6	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 60V, Negative-QTOF	splash10-0udi-2900000000-6e533ba339190c9b3f53	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 45V, Negative-QTOF	splash10-0udi-1900000000-72bc6c8b488e42481083	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 15V, Negative-QTOF	splash10-0udi-0690000000-42813bcf61f8d1e5a263	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 30V, Negative-QTOF	splash10-0udi-0950000000-1b4f03cb610cde16696e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 90V, Negative-QTOF	splash10-03xr-9500000000-0bbb2a446a4d8cd609c5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 75V, Negative-QTOF	splash10-0j4i-6900000000-e1e0422b1267e4b7caee	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 10V, Positive-QTOF	splash10-0a4i-0090000000-489f238039bb96ad5d8d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 20V, Positive-QTOF	splash10-0a4i-0090000000-66e8ffe989761257bc9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 40V, Positive-QTOF	splash10-0a4i-3490000000-5070ebc12c9a2f315b5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 10V, Negative-QTOF	splash10-0udi-0090000000-fe7a2300fdb2f99c70ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 20V, Negative-QTOF	splash10-0udi-0090000000-3da66f4d708f96b39376	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 40V, Negative-QTOF	splash10-0udi-4690000000-ac9ffc15a15fe15dda2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 10V, Positive-QTOF	splash10-0a4i-0090000000-15e0fcfc839c635e1c5b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 20V, Positive-QTOF	splash10-0a4i-0090000000-b3b5ce448b9db35987d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 40V, Positive-QTOF	splash10-03xr-4900000000-e60f0a2c763074c35a79	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 10V, Negative-QTOF	splash10-0udi-0090000000-198134c69f22ff575879	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 20V, Negative-QTOF	splash10-014i-9040000000-43621f23ef9eca2bb6a6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3-Chlorophenyl)hydrazonomalononitrile 40V, Negative-QTOF	splash10-001i-9200000000-28b6196d8b3508e4d1a7	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

2504

KEGG Compound ID

C11164

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carbonyl_cyanide_m-chlorophenyl_hydrazone

METLIN ID

Not Available

PubChem Compound

2603

PDB ID

Not Available

ChEBI ID

3259

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013851

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 (3-Chlorophenyl)hydrazonomalononitrile (HMDB0249720)

MOL for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

3D MOL for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

3D SDF for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

3D-SDF for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

PDB for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

3D PDB for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

SMILES for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

INCHI for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

Structure for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

3D Structure for HMDB0249720 ((3-Chlorophenyl)hydrazonomalononitrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra