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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:09:00 UTC

Update Date

2021-09-26 22:56:37 UTC

HMDB ID

HMDB0247137

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Description

8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom). Based on a literature review very few articles have been published on 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-benzo[d]azepine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 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

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       6.436   2.729   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.779   1.228   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.280   0.885   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       8.948  -0.502   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.280  -1.890   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.779  -2.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.575  -1.272   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.575   0.268   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.241   1.038   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.907   0.268   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.907  -1.272   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.241  -2.042   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       1.574   1.038   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0247137
HETATM    1  C1  UNL     1       0.562   2.622   0.218  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.181   1.351   0.514  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.490   1.308  -0.282  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.340   0.382   0.452  1.00  0.00           N  
HETATM    5  C4  UNL     1      -2.319  -0.935  -0.089  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.172  -1.784   0.298  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.148  -1.161   0.245  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.100  -2.177   0.068  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.450  -1.910  -0.021  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.912  -0.613   0.065  1.00  0.00           C  
HETATM   11 CL1  UNL     1       4.614  -0.248  -0.044  1.00  0.00          CL  
HETATM   12  C10 UNL     1       1.960   0.372   0.239  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.614   0.137   0.330  1.00  0.00           C  
HETATM   14  H1  UNL     1      -0.221   3.432   0.139  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.194   2.913   1.063  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.080   2.606  -0.762  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.516   1.430   1.591  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.934   2.332  -0.197  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.337   1.033  -1.323  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.303   0.779   0.456  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.413  -0.935  -1.215  1.00  0.00           H  
HETATM   22  H9  UNL     1      -3.257  -1.451   0.255  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.278  -2.262   1.300  1.00  0.00           H  
HETATM   24  H11 UNL     1      -1.157  -2.657  -0.421  1.00  0.00           H  
HETATM   25  H12 UNL     1       0.809  -3.218  -0.007  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.163  -2.736  -0.160  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.313   1.388   0.307  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   13   17
CONECT    3    4   18   19
CONECT    4    5   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    8   13
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   12
CONECT   12   13   13   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₄ClN

Average Molecular Weight

195.69

Monoisotopic Molecular Weight

195.0814772

IUPAC Name

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Traditional Name

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

CAS Registry Number

Not Available

SMILES

CC1CNCCC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C11H14ClN/c1-8-7-13-5-4-9-2-3-10(12)6-11(8)9/h2-3,6,8,13H,4-5,7H2,1H3

InChI Key

XTTZERNUQAFMOF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Not Available

Direct Parent

Benzazepines

Alternative Parents

Substituents

Benzazepine
Azepine
Aralkylamine
Benzenoid
Aryl halide
Aryl chloride
Secondary amine
Secondary aliphatic amine
Azacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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 (HMDB: HMDB0254161)

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	ALOGPS
logP	2.83	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	10.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.65 m³·mol⁻¹	ChemAxon
Polarizability	21.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	144.622	30932474
DeepCCS	[M-H]-	140.795	30932474
DeepCCS	[M-2H]-	178.327	30932474
DeepCCS	[M+Na]+	153.899	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	135.6	32859911
AllCCS	[M+NH4]+	144.0	32859911
AllCCS	[M+Na]+	145.2	32859911
AllCCS	[M-H]-	143.4	32859911
AllCCS	[M+Na-2H]-	144.0	32859911
AllCCS	[M+HCOO]-	144.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.7451 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.96 minutes	32390414

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine,1TMS,isomer #1	CC1CN([Si](C)(C)C)CCC2=CC=C(Cl)C=C21	1809.3	Semi standard non polar	33892256
8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine,1TMS,isomer #1	CC1CN([Si](C)(C)C)CCC2=CC=C(Cl)C=C21	1828.2	Standard non polar	33892256
8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine,1TMS,isomer #1	CC1CN([Si](C)(C)C)CCC2=CC=C(Cl)C=C21	2107.2	Standard polar	33892256
8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine,1TBDMS,isomer #1	CC1CN([Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C21	2001.2	Semi standard non polar	33892256
8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine,1TBDMS,isomer #1	CC1CN([Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C21	2077.3	Standard non polar	33892256
8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine,1TBDMS,isomer #1	CC1CN([Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C21	2294.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fsi-0900000000-5dc6dbcdb45e319f1c62	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 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 - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 10V, Positive-QTOF	splash10-0002-0900000000-6ccd461251b37d3f3063	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 20V, Positive-QTOF	splash10-0002-0900000000-e85e27c3c2878df99ce0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 40V, Positive-QTOF	splash10-014l-1900000000-131fb4bb5c89bae07d36	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 10V, Negative-QTOF	splash10-0006-2900000000-827bf1f1ca125c31b971	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 20V, Negative-QTOF	splash10-000x-6900000000-7cebee6aa46335a80142	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 40V, Negative-QTOF	splash10-001i-9200000000-509915ae88b636fac488	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

8640674

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10465263

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 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (HMDB0247137)

MOL for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

3D MOL for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

3D SDF for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

3D-SDF for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

PDB for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

3D PDB for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

SMILES for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

INCHI for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

Structure for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

3D Structure for HMDB0247137 (8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra