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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:47:24 UTC

Update Date

2021-09-26 23:08:27 UTC

HMDB ID

HMDB0254458

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Meptazinol

Description

Meptazinol belongs to the class of organic compounds known as azepanes. These are organic compounds containing a saturated seven member heterocycle, with one nitrogen atom. Meptazinol is a very strong basic compound (based on its pKa). A partial μ-opioid receptor agonist, its mixed agonist/antagonist activity affords it a lower risk of dependence and abuse than full μ agonists like morphine. Meptazinol is a 3-phenylazepane derivative, whereas the other phenazepanes like ethoheptazine and proheptazine are 4-phenylazepanes. Indications for use in moderate to severe pain, most commonly used to treat pain in obstetrics (childbirth). Meptazinol (trade name Meptid) is an opioid analgesic developed by Wyeth in the 1970s. Meptazinol exhibits not only a short onset of action, but also a shorter duration of action relative to other opioids such as morphine, pentazocine, or buprenorphine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Meptazinol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Meptazinol 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

HMDB0254458
     RDKit          3D
Meptazinol
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.4334   -2.3177   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -1.6419   -0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989   -0.1960   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4855   -0.1391    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9133   -0.7722    1.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2204   -0.7546    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1701   -0.0717    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7609    0.5674   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795    1.2815   -1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.5400   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746    0.7047   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103    1.3170   -1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127    1.9218   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    1.3524    0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1611    0.1440    0.7814 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8738   -0.6520    1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    0.1720    0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.3191   -2.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.9652   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5482   -3.4203   -1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2530   -2.2012    0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094   -1.6676   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429   -1.3312    1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.2610    2.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2166   -0.0252    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750    2.2754   -0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608    1.0746   -1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187    1.4291   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    0.0694   -2.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013    1.7796   -0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    0.2824   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079    1.7319   -1.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256    3.0526   -0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7391    2.1270    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279    1.0078    0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4057   -1.6168    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -0.0532    2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9325   -0.7251    1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    1.0080    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5623   -0.7075    1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
M  END


  Mrv1652306031607222D          

 17 18  0  0  0  0            999 V2000
   -2.0105    4.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594    6.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    3.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8043    4.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8043    5.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695    1.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695    2.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    1.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    3.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    5.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595    2.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030    4.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    3.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595    1.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    4.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    5.5047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0740    1.5431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  8  2  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  2  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254458

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(CCCCN(C)C1)C1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H23NO/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13/h6-8,11,17H,3-5,9-10,12H2,1-2H3

> <INCHI_KEY>
JLICHNCFTLFZJN-UHFFFAOYSA-N

> <FORMULA>
C15H23NO

> <MOLECULAR_WEIGHT>
233.355

> <EXACT_MASS>
233.177964365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.891270306565737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3-ethyl-1-methylazepan-3-yl)phenol

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.0681393325914303

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.227931719512801

> <JCHEM_PKA_STRONGEST_BASIC>
9.157919832639276

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
72.2777

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
meptazinol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254458
     RDKit          3D
Meptazinol
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.4334   -2.3177   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -1.6419   -0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989   -0.1960   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4855   -0.1391    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9133   -0.7722    1.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2204   -0.7546    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1701   -0.0717    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7609    0.5674   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795    1.2815   -1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.5400   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746    0.7047   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103    1.3170   -1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127    1.9218   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    1.3524    0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1611    0.1440    0.7814 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8738   -0.6520    1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    0.1720    0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.3191   -2.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.9652   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5482   -3.4203   -1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2530   -2.2012    0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094   -1.6676   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429   -1.3312    1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.2610    2.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2166   -0.0252    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750    2.2754   -0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608    1.0746   -1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187    1.4291   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    0.0694   -2.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013    1.7796   -0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    0.2824   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079    1.7319   -1.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256    3.0526   -0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7391    2.1270    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279    1.0078    0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4057   -1.6168    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -0.0532    2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9325   -0.7251    1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    1.0080    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5623   -0.7075    1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
M  END

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      -3.753   8.287   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.164  11.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.705   7.158   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.501   8.118   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.501   9.658   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.130   3.651   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.130   5.191   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.204   2.881   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.297   7.158   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.297  10.618   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.538   5.191   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.872   8.888   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.204   5.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.538   3.651   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.204   7.501   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.204  10.276   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -3.871   2.881   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   16                                                            
CONECT    3    1   15                                                       
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    7    8                                                       
CONECT    7    6   13                                                       
CONECT    8    6   14                                                       
CONECT    9    4   15                                                       
CONECT   10    5   16                                                       
CONECT   11   13   14                                                       
CONECT   12   15   16                                                       
CONECT   13    7   11   15                                                  
CONECT   14    8   11   17                                                  
CONECT   15    3    9   12   13                                             
CONECT   16    2   10   12                                                  
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0254458
HETATM    1  C1  UNL     1       0.433  -2.318  -1.694  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.342  -1.642  -0.624  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.099  -0.196  -0.345  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.486  -0.139   0.059  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.913  -0.772   1.207  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.220  -0.755   1.654  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.170  -0.072   0.927  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.761   0.567  -0.225  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.680   1.281  -1.013  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.433   0.540  -0.665  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.275   0.705  -1.528  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.510   1.317  -1.203  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.713   1.922  -0.822  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.996   1.352   0.629  1.00  0.00           C  
HETATM   15  N1  UNL     1      -2.161   0.144   0.781  1.00  0.00           N  
HETATM   16  C14 UNL     1      -2.874  -0.652   1.793  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.797   0.172   0.879  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.085  -2.319  -2.674  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.480  -1.965  -1.799  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.548  -3.420  -1.447  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.253  -2.201   0.326  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.409  -1.668  -0.917  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.243  -1.331   1.833  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.539  -1.261   2.560  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.217  -0.025   1.235  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.775   2.275  -0.747  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.261   1.075  -1.591  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.519   1.429  -1.806  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.305   0.069  -2.476  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.001   1.780  -0.281  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.983   0.282  -1.102  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.608   1.732  -1.457  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.726   3.053  -0.731  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.739   2.127   1.347  1.00  0.00           H  
HETATM   35  H18 UNL     1      -4.028   1.008   0.645  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.406  -1.617   1.972  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.761  -0.053   2.738  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.932  -0.725   1.542  1.00  0.00           H  
HETATM   39  H22 UNL     1      -0.310   1.008   1.451  1.00  0.00           H  
HETATM   40  H23 UNL     1      -0.562  -0.708   1.568  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   11   17
CONECT    4    5    5   10
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8   25
CONECT    8    9   10   10
CONECT    9   26
CONECT   10   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   17
CONECT   16   36   37   38
CONECT   17   39   40
END

HMDB0254458
     RDKit          3D
Meptazinol
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.4334   -2.3177   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -1.6419   -0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989   -0.1960   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4855   -0.1391    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9133   -0.7722    1.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2204   -0.7546    1.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1701   -0.0717    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7609    0.5674   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795    1.2815   -1.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.5400   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746    0.7047   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103    1.3170   -1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127    1.9218   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    1.3524    0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1611    0.1440    0.7814 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8738   -0.6520    1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    0.1720    0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.3191   -2.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.9652   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5482   -3.4203   -1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2530   -2.2012    0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094   -1.6676   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2429   -1.3312    1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.2610    2.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2166   -0.0252    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750    2.2754   -0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608    1.0746   -1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187    1.4291   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    0.0694   -2.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013    1.7796   -0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    0.2824   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079    1.7319   -1.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256    3.0526   -0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7391    2.1270    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0279    1.0078    0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4057   -1.6168    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -0.0532    2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9325   -0.7251    1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    1.0080    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5623   -0.7075    1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17  3  1  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cahill may roberts brand OF meptazinol hydrochloride	MeSH
Meptazinol hydrochloride	MeSH
Meptid	MeSH
Riemser brand OF meptazinol hydrochloride	MeSH
Shire brand OF meptazinol hydrochloride	MeSH

Chemical Formula

C₁₅H₂₃NO

Average Molecular Weight

233.355

Monoisotopic Molecular Weight

233.177964365

IUPAC Name

3-(3-ethyl-1-methylazepan-3-yl)phenol

Traditional Name

meptazinol

CAS Registry Number

Not Available

SMILES

CCC1(CCCCN(C)C1)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C15H23NO/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13/h6-8,11,17H,3-5,9-10,12H2,1-2H3

InChI Key

JLICHNCFTLFZJN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azepanes. These are organic compounds containing a saturated seven member heterocycle, with one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepanes

Sub Class

Not Available

Direct Parent

Azepanes

Alternative Parents

Substituents

Azepane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Amine
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen 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	3.75	ALOGPS
logP	3.07	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.23	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.28 m³·mol⁻¹	ChemAxon
Polarizability	27.89 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]+	157.68	30932474
DeepCCS	[M-H]-	155.322	30932474
DeepCCS	[M-2H]-	188.277	30932474
DeepCCS	[M+Na]+	163.773	30932474
AllCCS	[M+H]+	153.5	32859911
AllCCS	[M+H-H2O]+	149.5	32859911
AllCCS	[M+NH4]+	157.3	32859911
AllCCS	[M+Na]+	158.3	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	163.0	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Meptazinol	CCC1(CCCCN(C)C1)C1=CC(O)=CC=C1	2824.1	Standard polar	33892256
Meptazinol	CCC1(CCCCN(C)C1)C1=CC(O)=CC=C1	1874.2	Standard non polar	33892256
Meptazinol	CCC1(CCCCN(C)C1)C1=CC(O)=CC=C1	1918.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Meptazinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-3920000000-befb017ce35fa50f8460	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meptazinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meptazinol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meptazinol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol LC-ESI-QFT , positive-QTOF	splash10-001i-0090000000-e2ccc6bbd7aaeb81bea9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol LC-ESI-QFT , positive-QTOF	splash10-001i-0090000000-a816abbf7cdc7787b726	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol LC-ESI-QFT , positive-QTOF	splash10-053r-1970000000-325f14eb89956314e4ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol LC-ESI-QFT , positive-QTOF	splash10-0a4i-1900000000-0074e1202dfc45b8aff5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol LC-ESI-QFT , positive-QTOF	splash10-0a4i-2900000000-78ca29f251cbfe79f6b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol LC-ESI-QFT , positive-QTOF	splash10-0a4i-3900000000-5bee97314182dc1e358f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol 90V, Positive-QTOF	splash10-0a4i-3900000000-0c9fad6577f860defc97	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol 75V, Positive-QTOF	splash10-0a4i-1900000000-0685989e712dcfbbb00e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol 60V, Positive-QTOF	splash10-0a4i-1900000000-efb048446f1217337e46	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol 45V, Positive-QTOF	splash10-053r-0970000000-62ae7cc6fb7ce94ac50c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol 30V, Positive-QTOF	splash10-001i-0090000000-fb7cd692dad7ff04481e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meptazinol 15V, Positive-QTOF	splash10-001i-0090000000-cfc52a7a204988123f3d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 10V, Positive-QTOF	splash10-001i-0090000000-7b1c1336857703b5f3fc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 20V, Positive-QTOF	splash10-001i-0590000000-41ee9dce3bde65b478ed	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 40V, Positive-QTOF	splash10-0005-5900000000-8ef5370d37715e4c7ede	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 10V, Negative-QTOF	splash10-001i-0090000000-95af27276d2e275635ff	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 20V, Negative-QTOF	splash10-001i-0190000000-d945ae8103eac25b0c3f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 40V, Negative-QTOF	splash10-0006-9420000000-087ad0bbd7a051b9cc7c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 10V, Positive-QTOF	splash10-001i-0590000000-8f98daea23ac3e8561a2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 20V, Positive-QTOF	splash10-01pk-1920000000-8db79d79fc95a7253d41	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 40V, Positive-QTOF	splash10-0bta-3910000000-b3164247692ff0dfc289	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 10V, Negative-QTOF	splash10-001i-0090000000-1df18e692404252b2c98	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 20V, Negative-QTOF	splash10-0f89-0090000000-12c0a21b58452efe71f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meptazinol 40V, Negative-QTOF	splash10-0f8i-0790000000-be0c3df2440d1834a1a3	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

DB13478

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meptazinol

METLIN ID

Not Available

PubChem Compound

41049

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 Meptazinol (HMDB0254458)

MOL for HMDB0254458 (Meptazinol)

3D MOL for HMDB0254458 (Meptazinol)

3D SDF for HMDB0254458 (Meptazinol)

3D-SDF for HMDB0254458 (Meptazinol)

PDB for HMDB0254458 (Meptazinol)

3D PDB for HMDB0254458 (Meptazinol)

SMILES for HMDB0254458 (Meptazinol)

INCHI for HMDB0254458 (Meptazinol)

Structure for HMDB0254458 (Meptazinol)

3D Structure for HMDB0254458 (Meptazinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra