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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:22:42 UTC

Update Date

2021-09-26 22:55:23 UTC

HMDB ID

HMDB0246351

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Aminoazobenzene

Description

4-Aminoazobenzene, also known as aniline yellow, belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring. Based on a literature review a significant number of articles have been published on 4-Aminoazobenzene. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-aminoazobenzene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Aminoazobenzene 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


  Mrv1533004261515202D          

 15 16  0  0  0  0            999 V2000
    1.4289   -4.1250    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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   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
    1.4289    0.8250    0.0000 C   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    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  4  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246351

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC=C(C=C1)N=NC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2

> <INCHI_KEY>
QPQKUYVSJWQSDY-UHFFFAOYSA-N

> <FORMULA>
C12H11N3

> <MOLECULAR_WEIGHT>
197.241

> <EXACT_MASS>
197.095297366

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.911223093030703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-phenyldiazen-1-yl)aniline

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.5502135353333335

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.0612959045444743

> <JCHEM_POLAR_SURFACE_AREA>
50.739999999999995

> <JCHEM_REFRACTIVITY>
65.0774

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aniline yellow

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0246351
HETATM    1  N1  UNL     1       5.463   0.396   0.424  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.053   0.352   0.440  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.341  -0.346   1.409  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.963  -0.381   1.412  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.238   0.288   0.438  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.191   0.253   0.442  1.00  0.00           N  
HETATM    7  N3  UNL     1      -0.862  -0.528  -0.297  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.272  -0.466  -0.199  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.959  -1.459   0.447  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.340  -1.384   0.534  1.00  0.00           C  
HETATM   11  C8  UNL     1      -5.017  -0.315  -0.025  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.308   0.675  -0.671  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.935   0.597  -0.756  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.916   0.991  -0.537  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.293   1.009  -0.518  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.949   1.305   0.466  1.00  0.00           H  
HETATM   17  H2  UNL     1       6.007  -0.479   0.371  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.900  -0.862   2.160  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.396  -0.921   2.161  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.467  -2.324   0.904  1.00  0.00           H  
HETATM   21  H6  UNL     1      -4.931  -2.154   1.040  1.00  0.00           H  
HETATM   22  H7  UNL     1      -6.092  -0.231   0.029  1.00  0.00           H  
HETATM   23  H8  UNL     1      -4.852   1.501  -1.100  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.438   1.410  -1.278  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.340   1.510  -1.294  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.802   1.563  -1.288  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3    3   15
CONECT    3    4   18
CONECT    4    5    5   19
CONECT    5    6   14
CONECT    6    7    7
CONECT    7    8
CONECT    8    9    9   13
CONECT    9   10   20
CONECT   10   11   11   21
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   24
CONECT   14   15   15   25
CONECT   15   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
C.I. solvent yellow 1	HMDB
4-(Phenyldiazenyl)aniline	HMDB
Para aminoazobenzene	HMDB
Aniline yellow	HMDB
Para-aminoazobenzene	HMDB
p-Aminoazobenzene	HMDB
p Aminoazobenzene	HMDB

Chemical Formula

C₁₂H₁₁N₃

Average Molecular Weight

197.241

Monoisotopic Molecular Weight

197.095297366

IUPAC Name

4-(2-phenyldiazen-1-yl)aniline

Traditional Name

aniline yellow

CAS Registry Number

Not Available

SMILES

NC1=CC=C(C=C1)N=NC1=CC=CC=C1

InChI Identifier

InChI=1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2

InChI Key

QPQKUYVSJWQSDY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azobenzenes

Sub Class

Not Available

Direct Parent

Azobenzenes

Alternative Parents

Substituents

Azobenzene
Aniline or substituted anilines
Benzenoid
Monocyclic benzene moiety
Azo compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.02	ALOGPS
logP	3.55	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	3.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.08 m³·mol⁻¹	ChemAxon
Polarizability	21.91 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]+	146.876	30932474
DeepCCS	[M-H]-	144.481	30932474
DeepCCS	[M-2H]-	178.423	30932474
DeepCCS	[M+Na]+	153.035	30932474
AllCCS	[M+H]+	144.8	32859911
AllCCS	[M+H-H2O]+	140.5	32859911
AllCCS	[M+NH4]+	148.7	32859911
AllCCS	[M+Na]+	149.9	32859911
AllCCS	[M-H]-	146.7	32859911
AllCCS	[M+Na-2H]-	146.5	32859911
AllCCS	[M+HCOO]-	146.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Aminoazobenzene	NC1=CC=C(C=C1)N=NC1=CC=CC=C1	3048.6	Standard polar	33892256
4-Aminoazobenzene	NC1=CC=C(C=C1)N=NC1=CC=CC=C1	2146.8	Standard non polar	33892256
4-Aminoazobenzene	NC1=CC=C(C=C1)N=NC1=CC=CC=C1	2104.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Aminoazobenzene,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(N=NC2=CC=CC=C2)C=C1	2332.4	Semi standard non polar	33892256
4-Aminoazobenzene,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(N=NC2=CC=CC=C2)C=C1	2253.5	Standard non polar	33892256
4-Aminoazobenzene,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(N=NC2=CC=CC=C2)C=C1	2825.9	Standard polar	33892256
4-Aminoazobenzene,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(N=NC2=CC=CC=C2)C=C1)[Si](C)(C)C	2233.8	Semi standard non polar	33892256
4-Aminoazobenzene,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(N=NC2=CC=CC=C2)C=C1)[Si](C)(C)C	2295.3	Standard non polar	33892256
4-Aminoazobenzene,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(N=NC2=CC=CC=C2)C=C1)[Si](C)(C)C	2743.4	Standard polar	33892256
4-Aminoazobenzene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(N=NC2=CC=CC=C2)C=C1	2556.2	Semi standard non polar	33892256
4-Aminoazobenzene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(N=NC2=CC=CC=C2)C=C1	2454.3	Standard non polar	33892256
4-Aminoazobenzene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(N=NC2=CC=CC=C2)C=C1	2944.2	Standard polar	33892256
4-Aminoazobenzene,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(N=NC2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C	2679.4	Semi standard non polar	33892256
4-Aminoazobenzene,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(N=NC2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C	2699.5	Standard non polar	33892256
4-Aminoazobenzene,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(N=NC2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C	2855.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminoazobenzene GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ne-6900000000-4602c5e55a79aded6128	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminoazobenzene 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 - 4-Aminoazobenzene 30V, Positive-QTOF	splash10-0002-4900000000-46c0a270af4ff934f0de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Aminoazobenzene 15V, Positive-QTOF	splash10-0002-2900000000-3b31b570d35a1fe4243b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Aminoazobenzene 45V, Positive-QTOF	splash10-0002-9400000000-b4a4523997c0e2ba0cdc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Aminoazobenzene 35V, Positive-QTOF	splash10-0002-6900000000-67e86e0e53807effb753	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Aminoazobenzene 60V, Positive-QTOF	splash10-0002-9200000000-cd12e3f28dbd40e3a4b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Aminoazobenzene 75V, Positive-QTOF	splash10-0002-9200000000-0c6736337274bf1d97fb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Aminoazobenzene 90V, Positive-QTOF	splash10-0002-9200000000-fd759870e3ff45c192f2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoazobenzene 10V, Positive-QTOF	splash10-0002-0900000000-732fba02eb75c1e91307	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoazobenzene 20V, Positive-QTOF	splash10-0007-9600000000-ba8e0f9fc3931859962f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoazobenzene 40V, Positive-QTOF	splash10-00kf-9500000000-a856a0a9f7f025385f49	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoazobenzene 10V, Negative-QTOF	splash10-0002-0900000000-081eee6e904048150332	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoazobenzene 20V, Negative-QTOF	splash10-0002-1900000000-eeae8a47875e99e83fb0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoazobenzene 40V, Negative-QTOF	splash10-00dl-4900000000-d5ac46ba9b25bf770309	2021-10-12	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

10447135

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aniline Yellow

METLIN ID

Not Available

PubChem Compound

6051

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 4-Aminoazobenzene (HMDB0246351)

MOL for HMDB0246351 (4-Aminoazobenzene)

3D MOL for HMDB0246351 (4-Aminoazobenzene)

3D SDF for HMDB0246351 (4-Aminoazobenzene)

3D-SDF for HMDB0246351 (4-Aminoazobenzene)

PDB for HMDB0246351 (4-Aminoazobenzene)

3D PDB for HMDB0246351 (4-Aminoazobenzene)

SMILES for HMDB0246351 (4-Aminoazobenzene)

INCHI for HMDB0246351 (4-Aminoazobenzene)

Structure for HMDB0246351 (4-Aminoazobenzene)

3D Structure for HMDB0246351 (4-Aminoazobenzene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra