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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:35:14 UTC

Update Date

2021-09-26 23:16:30 UTC

HMDB ID

HMDB0259127

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tretazicar

Description

Tretazicar belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group. Based on a literature review very few articles have been published on Tretazicar. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tretazicar is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tretazicar 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

CB1
  Mrv0541 02231217332D          

 18 19  0  0  0  0            999 V2000
    1.0371    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -0.5693    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4661   -0.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516   -1.3943    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.3227   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918   -1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371   -1.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1063    1.0807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9313    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5188    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227    1.9057    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.3918    2.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371    2.3182    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 13  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  CHG  4   7   1   9  -1  16   1  18  -1
M  END
> <DATABASE_ID>
HMDB0259127

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)C1=CC(N2CC2)=C(C=C1[N+]([O-])=O)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8N4O5/c10-9(14)5-3-7(11-1-2-11)8(13(17)18)4-6(5)12(15)16/h3-4H,1-2H2,(H2,10,14)

> <INCHI_KEY>
WOCXQMCIOTUMJV-UHFFFAOYSA-N

> <FORMULA>
C9H8N4O5

> <MOLECULAR_WEIGHT>
252.1836

> <EXACT_MASS>
252.049469386

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.5563622021431

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(aziridin-1-yl)-2,4-dinitrobenzamide

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
0.6403734043333335

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.291113210200782

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4858433476278665

> <JCHEM_POLAR_SURFACE_AREA>
137.73999999999998

> <JCHEM_REFRACTIVITY>
62.245400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tretazicar

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: CB1                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.936   1.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.936  -0.293   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.602  -1.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.731  -0.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.731   1.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.602   2.017   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.270  -1.063   0.000  0.00  0.00           N+1
HETATM    8  O   UNK     0       4.603  -0.293   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.270  -2.603   0.000  0.00  0.00           O-1
HETATM   10  C   UNK     0       0.602  -2.603   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.731  -3.373   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       1.936  -3.373   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -2.065   2.017   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -3.605   2.017   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.835   3.351   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.602   3.557   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0      -0.731   4.327   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.936   4.327   0.000  0.00  0.00           O-1
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    1    5   16                                                  
CONECT    7    2    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   13   14                                                       
CONECT   16    6   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0259127
HETATM    1  N1  UNL     1       3.807   1.285   0.422  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.464   1.492   0.127  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.129   2.749   0.010  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.425   0.508  -0.057  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.078   0.917  -0.072  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.970   0.037  -0.217  1.00  0.00           C  
HETATM    7  N2  UNL     1      -2.313   0.532  -0.198  1.00  0.00           N  
HETATM    8  C5  UNL     1      -3.664   0.891  -0.452  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.111   1.382   0.815  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.732  -1.295  -0.356  1.00  0.00           C  
HETATM   11  N3  UNL     1      -1.774  -2.273  -0.513  1.00  0.00           N1+
HETATM   12  O2  UNL     1      -1.600  -3.451  -0.111  1.00  0.00           O  
HETATM   13  O3  UNL     1      -2.944  -1.912  -1.097  1.00  0.00           O1-
HETATM   14  C8  UNL     1       0.580  -1.728  -0.346  1.00  0.00           C  
HETATM   15  C9  UNL     1       1.648  -0.818  -0.197  1.00  0.00           C  
HETATM   16  N4  UNL     1       2.920  -1.420  -0.229  1.00  0.00           N1+
HETATM   17  O4  UNL     1       3.888  -0.914  -0.766  1.00  0.00           O  
HETATM   18  O5  UNL     1       3.078  -2.677   0.314  1.00  0.00           O1-
HETATM   19  H1  UNL     1       4.557   1.637  -0.232  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.173   0.798   1.281  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.098   1.966   0.038  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.445   0.118  -0.358  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.786   1.649  -1.268  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.301   0.870   1.771  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.761   2.435   0.853  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.752  -2.779  -0.455  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3    4
CONECT    4    5    5   15
CONECT    5    6   21
CONECT    6    7   10   10
CONECT    7    8    9
CONECT    8    9   22   23
CONECT    9   24   25
CONECT   10   11   14
CONECT   11   12   12   13
CONECT   14   15   15   26
CONECT   15   16
CONECT   16   17   17   18
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
CB-1954Tretazicar	ChEMBL
Aziridine dinitrobenzamide	MeSH
5-(1-Aziridinyl)-2,4-dinitrobenzamide	MeSH
5-Aziridinyl-2,4-dinitrobenzamide	MeSH
5-(Aziridin-1-yl)-2,4-dinitrobenzene-1-carboximidate	Generator

Chemical Formula

C₉H₈N₄O₅

Average Molecular Weight

252.1836

Monoisotopic Molecular Weight

252.049469386

IUPAC Name

5-(aziridin-1-yl)-2,4-dinitrobenzamide

Traditional Name

tretazicar

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CC(N2CC2)=C(C=C1[N+]([O-])=O)[N+]([O-])=O

InChI Identifier

InChI=1S/C9H8N4O5/c10-9(14)5-3-7(11-1-2-11)8(13(17)18)4-6(5)12(15)16/h3-4H,1-2H2,(H2,10,14)

InChI Key

WOCXQMCIOTUMJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Dinitroanilines

Alternative Parents

Substituents

Dinitroaniline
Aminobenzamide
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Indole
Nitrobenzene
Phenylaziridine
Nitroaromatic compound
Benzoyl
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Amino acid or derivatives
Carboxamide group
C-nitro compound
Organic nitro compound
Primary carboxylic acid amide
Tertiary amine
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Aziridine
Organic 1,3-dipolar compound
Azacycle
Carboxylic acid derivative
Organooxygen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organic zwitterion
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	0.04	ALOGPS
logP	0.64	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.29	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.25 m³·mol⁻¹	ChemAxon
Polarizability	21.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	156.406	30932474
DeepCCS	[M-H]-	153.146	30932474
DeepCCS	[M-2H]-	188.141	30932474
DeepCCS	[M+Na]+	164.304	30932474
AllCCS	[M+H]+	152.0	32859911
AllCCS	[M+H-H2O]+	148.3	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.5	32859911
AllCCS	[M-H]-	149.4	32859911
AllCCS	[M+Na-2H]-	148.9	32859911
AllCCS	[M+HCOO]-	148.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tretazicar	NC(=O)C1=CC(N2CC2)=C(C=C1[N+]([O-])=O)[N+]([O-])=O	3007.9	Standard polar	33892256
Tretazicar	NC(=O)C1=CC(N2CC2)=C(C=C1[N+]([O-])=O)[N+]([O-])=O	2199.4	Standard non polar	33892256
Tretazicar	NC(=O)C1=CC(N2CC2)=C(C=C1[N+]([O-])=O)[N+]([O-])=O	2506.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tretazicar,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-]	2544.8	Semi standard non polar	33892256
Tretazicar,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-]	2492.0	Standard non polar	33892256
Tretazicar,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-]	3158.3	Standard polar	33892256
Tretazicar,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-])[Si](C)(C)C	2537.4	Semi standard non polar	33892256
Tretazicar,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-])[Si](C)(C)C	2504.7	Standard non polar	33892256
Tretazicar,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-])[Si](C)(C)C	2990.4	Standard polar	33892256
Tretazicar,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-]	2887.2	Semi standard non polar	33892256
Tretazicar,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-]	2655.1	Standard non polar	33892256
Tretazicar,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-]	3217.8	Standard polar	33892256
Tretazicar,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-])[Si](C)(C)C(C)(C)C	3079.8	Semi standard non polar	33892256
Tretazicar,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-])[Si](C)(C)C(C)(C)C	2906.6	Standard non polar	33892256
Tretazicar,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC(N2CC2)=C([N+](=O)[O-])C=C1[N+](=O)[O-])[Si](C)(C)C(C)(C)C	3044.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tretazicar GC-MS (Non-derivatized) - 70eV, Positive	splash10-07w9-9560000000-441bfb4f7430881cfcfb	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tretazicar 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 - Tretazicar 10V, Positive-QTOF	splash10-0udi-0090000000-13592795f5d5d4a20a19	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tretazicar 20V, Positive-QTOF	splash10-002b-0090000000-054886eb585439f0f216	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tretazicar 40V, Positive-QTOF	splash10-002g-6590000000-2925ed97d1d0abe1e1e7	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tretazicar 10V, Negative-QTOF	splash10-0udi-0090000000-6cf7cf9e6b1787bab672	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tretazicar 20V, Negative-QTOF	splash10-0udi-1090000000-40e60464b6c4312e0899	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tretazicar 40V, Negative-QTOF	splash10-00kg-5090000000-e0ca795e334a0f98cded	2017-07-26	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

DB04253

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

80403

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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 Tretazicar (HMDB0259127)

MOL for HMDB0259127 (Tretazicar)

3D MOL for HMDB0259127 (Tretazicar)

3D SDF for HMDB0259127 (Tretazicar)

3D-SDF for HMDB0259127 (Tretazicar)

PDB for HMDB0259127 (Tretazicar)

3D PDB for HMDB0259127 (Tretazicar)

SMILES for HMDB0259127 (Tretazicar)

INCHI for HMDB0259127 (Tretazicar)

Structure for HMDB0259127 (Tretazicar)

3D Structure for HMDB0259127 (Tretazicar)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra