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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:52:10 UTC

Update Date

2021-09-26 22:56:11 UTC

HMDB ID

HMDB0246857

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydronorketamine

Description

6-amino-6-(2-chlorophenyl)cyclohex-2-en-1-one belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. Based on a literature review very few articles have been published on 6-amino-6-(2-chlorophenyl)cyclohex-2-en-1-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydronorketamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydronorketamine 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


  Mrv1652306031609462D          

 15 16  0  0  0  0            999 V2000
    3.0539   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7683    0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7683    0.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822    1.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    0.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    0.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539    1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0946    1.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249    1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539    2.1885    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    1.9955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768    2.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246857

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1(CCC=CC1=O)C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C12H12ClNO/c13-10-6-2-1-5-9(10)12(14)8-4-3-7-11(12)15/h1-3,5-7H,4,8,14H2

> <INCHI_KEY>
BXBPJMHHWPXBJL-UHFFFAOYSA-N

> <FORMULA>
C12H12ClNO

> <MOLECULAR_WEIGHT>
221.68

> <EXACT_MASS>
221.0607417

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.411839753094235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-amino-6-(2-chlorophenyl)cyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.912545762

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.156899059506948

> <JCHEM_PKA_STRONGEST_BASIC>
7.192427781638867

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
61.8725

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-amino-6-(2-chlorophenyl)cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       5.701  -0.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.034   0.235   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   2.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.990   0.831   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.367   0.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.034   1.775   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.527   3.457   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.506   1.098   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.367   1.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.701   2.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.043   3.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.033   2.545   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       5.701   4.085   0.000  0.00  0.00          Cl+0
HETATM   14  N   UNK     0       4.023   3.725   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       2.570   5.172   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    1    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   10   12                                                  
CONECT   10    6    9   13                                                  
CONECT   11    7   12   15                                                  
CONECT   12    8    9   11   14                                             
CONECT   13   10                                                            
CONECT   14   12                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0246857
HETATM    1  N1  UNL     1      -0.753  -1.761   0.348  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.510  -0.298   0.251  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.926  -0.130   0.150  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.718  -1.267   0.172  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.102  -1.222   0.086  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.752  -0.034  -0.026  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.005   1.113  -0.051  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.632   1.038   0.037  1.00  0.00           C  
HETATM    9 CL1  UNL     1       0.744   2.507  -0.005  1.00  0.00          CL  
HETATM   10  C8  UNL     1      -1.278   0.320   1.300  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.420   1.190   0.901  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.208   0.629  -0.208  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.544   0.057  -1.198  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.096   0.042  -1.075  1.00  0.00           C  
HETATM   15  O1  UNL     1      -0.397   0.310  -2.070  1.00  0.00           O  
HETATM   16  H1  UNL     1      -0.448  -2.154   1.237  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.551  -2.258  -0.517  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.317  -2.277   0.258  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.687  -2.136   0.106  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.834   0.059  -0.096  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.520   2.083  -0.141  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.790  -0.501   1.912  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.678   0.781   2.141  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.106   2.204   0.493  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.086   1.379   1.801  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.299   0.682  -0.213  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.075  -0.356  -2.046  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3   10   14
CONECT    3    4    4    8
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   20
CONECT    7    8    8   21
CONECT    8    9
CONECT   10   11   22   23
CONECT   11   12   24   25
CONECT   12   13   13   26
CONECT   13   14   27
CONECT   14   15   15
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6-Dehydronorketamine, (+-)-isomer	MeSH

Chemical Formula

C₁₂H₁₂ClNO

Average Molecular Weight

221.68

Monoisotopic Molecular Weight

221.0607417

IUPAC Name

6-amino-6-(2-chlorophenyl)cyclohex-2-en-1-one

Traditional Name

6-amino-6-(2-chlorophenyl)cyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

NC1(CCC=CC1=O)C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C12H12ClNO/c13-10-6-2-1-5-9(10)12(14)8-4-3-7-11(12)15/h1-3,5-7H,4,8,14H2

InChI Key

BXBPJMHHWPXBJL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Cyclohexenone
Aralkylamine
Aryl chloride
Aryl halide
Ketone
Cyclic ketone
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	2.35	ALOGPS
logP	2.91	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	17.16	ChemAxon
pKa (Strongest Basic)	7.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.87 m³·mol⁻¹	ChemAxon
Polarizability	22.41 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]+	146.633	30932474
DeepCCS	[M-H]-	144.275	30932474
DeepCCS	[M-2H]-	178.931	30932474
DeepCCS	[M+Na]+	153.504	30932474
AllCCS	[M+H]+	148.3	32859911
AllCCS	[M+H-H2O]+	144.2	32859911
AllCCS	[M+NH4]+	152.2	32859911
AllCCS	[M+Na]+	153.3	32859911
AllCCS	[M-H]-	148.6	32859911
AllCCS	[M+Na-2H]-	148.8	32859911
AllCCS	[M+HCOO]-	149.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydronorketamine	NC1(CCC=CC1=O)C1=CC=CC=C1Cl	2573.5	Standard polar	33892256
Dehydronorketamine	NC1(CCC=CC1=O)C1=CC=CC=C1Cl	1729.0	Standard non polar	33892256
Dehydronorketamine	NC1(CCC=CC1=O)C1=CC=CC=C1Cl	1883.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydronorketamine,1TMS,isomer #1	C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCC=CC1=O	2027.8	Semi standard non polar	33892256
Dehydronorketamine,1TMS,isomer #1	C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCC=CC1=O	1944.4	Standard non polar	33892256
Dehydronorketamine,1TMS,isomer #1	C[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCC=CC1=O	2547.0	Standard polar	33892256
Dehydronorketamine,2TMS,isomer #1	C[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCC=CC1=O)[Si](C)(C)C	2064.3	Semi standard non polar	33892256
Dehydronorketamine,2TMS,isomer #1	C[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCC=CC1=O)[Si](C)(C)C	2099.5	Standard non polar	33892256
Dehydronorketamine,2TMS,isomer #1	C[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCC=CC1=O)[Si](C)(C)C	2539.4	Standard polar	33892256
Dehydronorketamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCC=CC1=O	2252.5	Semi standard non polar	33892256
Dehydronorketamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCC=CC1=O	2170.4	Standard non polar	33892256
Dehydronorketamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1(C2=CC=CC=C2Cl)CCC=CC1=O	2655.3	Standard polar	33892256
Dehydronorketamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCC=CC1=O)[Si](C)(C)C(C)(C)C	2548.6	Semi standard non polar	33892256
Dehydronorketamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCC=CC1=O)[Si](C)(C)C(C)(C)C	2487.5	Standard non polar	33892256
Dehydronorketamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1(C2=CC=CC=C2Cl)CCC=CC1=O)[Si](C)(C)C(C)(C)C	2615.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydronorketamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-3910000000-316f4972f79e5e577c38	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydronorketamine 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 - Dehydronorketamine 10V, Positive-QTOF	splash10-00di-0090000000-0351b70f87ee951fbaff	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 20V, Positive-QTOF	splash10-00dl-1960000000-2f449f833c8367057012	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 40V, Positive-QTOF	splash10-000l-2900000000-a9107f029891be9c05b7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 10V, Negative-QTOF	splash10-00di-0090000000-4aec5a16f880b3f1aae3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 20V, Negative-QTOF	splash10-00di-0490000000-9e2e79d8522230b26f0f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 40V, Negative-QTOF	splash10-0a4i-2900000000-821c0bc83cad13ae972b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 10V, Positive-QTOF	splash10-05fr-0090000000-e80c1e536528302c39c6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 20V, Positive-QTOF	splash10-0a4i-0590000000-e4b36283b3e6cc935c17	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 40V, Positive-QTOF	splash10-000i-5900000000-a27fd1239d8f2b3c4620	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 10V, Negative-QTOF	splash10-00di-0290000000-2f40f8071ff3d6cc2854	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 20V, Negative-QTOF	splash10-0ab9-2940000000-e426b567ca303d3dcdb5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronorketamine 40V, Negative-QTOF	splash10-0159-9180000000-635a9bc4e3cd29c9deb0	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

142954

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162835

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 Dehydronorketamine (HMDB0246857)

MOL for HMDB0246857 (Dehydronorketamine)

3D MOL for HMDB0246857 (Dehydronorketamine)

3D SDF for HMDB0246857 (Dehydronorketamine)

3D-SDF for HMDB0246857 (Dehydronorketamine)

PDB for HMDB0246857 (Dehydronorketamine)

3D PDB for HMDB0246857 (Dehydronorketamine)

SMILES for HMDB0246857 (Dehydronorketamine)

INCHI for HMDB0246857 (Dehydronorketamine)

Structure for HMDB0246857 (Dehydronorketamine)

3D Structure for HMDB0246857 (Dehydronorketamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra