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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 04:06:22 UTC

Update Date

2022-09-22 17:45:01 UTC

HMDB ID

HMDB0249590

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cannabinol

Description

Cannabinol belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Thus, cannabinol is considered to be an aromatic polyketide. Based on a literature review very few articles have been published on Cannabinol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cannabinol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cannabinol 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

HMDB0249590
     RDKit          3D
Cannabinol
 49 51  0  0  0  0  0  0  0  0999 V2000
    7.3852    0.3520   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004    0.5953   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2757   -0.0298    0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779    0.1566    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895   -0.4528   -0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.2239   -0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    0.9147   -0.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    1.1097   -0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7868    2.2693   -1.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    0.1828   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5074   -0.9770    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -1.1561    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005   -1.8896    1.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757   -1.8034    1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3244   -3.0710    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943   -1.7483    2.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2980   -0.5949    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6624   -0.4544    0.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2529    0.6753    0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    1.6306   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1749    2.8532   -0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1378    1.4848   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5450    0.3637   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7987    0.6418   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5442   -1.1054    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786    0.4090    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -0.3564    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298    1.2180    0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4036   -0.0145   -1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399   -1.5505   -0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989    1.6295   -1.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    2.9672   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646   -2.0625    0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898   -2.8247    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6461   -3.7173    1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -3.6370    0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -2.7707    3.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -1.0922    3.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9327   -1.3948    2.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2862   -1.1725    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3373    0.8476    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4626    3.6922   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5859    2.6673   -1.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9975    3.1697   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6047    2.2408   -1.0194 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
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 12  6  1  0
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  1 25  1  0
  1 26  1  0
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  4 31  1  0
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  5 33  1  0
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  7 35  1  0
  9 36  1  0
 12 37  1  0
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 18 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
M  END


  Mrv1652309272007282D          

 23 25  0  0  0  0            999 V2000
 9996.990010000.5485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.851910000.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.566410000.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.280810000.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.999310000.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.713810000.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2238 9997.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1744 9997.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8421 9999.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2733 9999.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5590 9998.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5590 9998.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2733 9997.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.134110000.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.419810000.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.705410000.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1342 9999.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7041 9999.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9896 9998.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9896 9998.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7041 9997.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4185 9998.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4185 9998.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11  9  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 14  1  0  0  0  0
 14  2  1  0  0  0  0
  1 16  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21  8  1  0  0  0  0
 21  7  1  0  0  0  0
 13 20  1  0  0  0  0
 19 10  1  0  0  0  0
 16 18  2  0  0  0  0
 23 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249590

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3

> <INCHI_KEY>
VBGLYOIFKLUMQG-UHFFFAOYSA-N

> <FORMULA>
C21H26O2

> <MOLECULAR_WEIGHT>
310.437

> <EXACT_MASS>
310.193280077

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.75262448976888

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen-1-ol

> <ALOGPS_LOGP>
6.58

> <JCHEM_LOGP>
6.412731023666666

> <ALOGPS_LOGS>
-5.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.318134306693421

> <JCHEM_PKA_STRONGEST_BASIC>
-4.922121880517445

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
95.73629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.39e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cannabinol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249590
     RDKit          3D
Cannabinol
 49 51  0  0  0  0  0  0  0  0999 V2000
    7.3852    0.3520   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004    0.5953   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2757   -0.0298    0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779    0.1566    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895   -0.4528   -0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.2239   -0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    0.9147   -0.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    1.1097   -0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7868    2.2693   -1.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    0.1828   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5074   -0.9770    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -1.1561    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005   -1.8896    1.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757   -1.8034    1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3244   -3.0710    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943   -1.7483    2.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2980   -0.5949    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6624   -0.4544    0.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2529    0.6753    0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    1.6306   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1749    2.8532   -0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1378    1.4848   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5450    0.3637   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7987    0.6418   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8780    0.9948    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3862   -0.3564    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1898   -2.8247    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6461   -3.7173    1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -3.6370    0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -2.7707    3.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -1.0922    3.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9327   -1.3948    2.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2862   -1.1725    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3373    0.8476    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4626    3.6922   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5859    2.6673   -1.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9975    3.1697   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6047    2.2408   -1.0194 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  1  0
  5  6  1  0
  6  7  2  0
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  1 24  1  0
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  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8661.0488667.691   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8666.3908667.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.7248666.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.0588667.691   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8670.3998666.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.7338667.691   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.3518661.099   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.3928661.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8657.0398665.382   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8659.7108665.377   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8658.3778664.607   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8658.3778663.067   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.7108662.297   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.0508666.921   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.7178667.691   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.3838666.921   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.0508665.382   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.3818665.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8661.0478664.608   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.0478663.068   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8662.3818662.299   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8663.7148663.068   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8663.7148664.608   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2    3   14                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7   21                                                            
CONECT    8   21                                                            
CONECT    9   11                                                            
CONECT   10   11   19                                                       
CONECT   11   10   12    9                                                  
CONECT   12   11   13                                                       
CONECT   13   12   20                                                       
CONECT   14   15   17    2                                                  
CONECT   15   14   16                                                       
CONECT   16   15    1   18                                                  
CONECT   17   14   23                                                       
CONECT   18   19   23   16                                                  
CONECT   19   18   20   10                                                  
CONECT   20   19   21   13                                                  
CONECT   21   20   22    8    7                                             
CONECT   22   21   23                                                       
CONECT   23   18   22   17                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0249590
HETATM    1  C1  UNL     1       7.385   0.352  -0.566  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.900   0.595  -0.611  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.276  -0.030   0.590  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.778   0.157   0.644  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.089  -0.453  -0.558  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.627  -0.224  -0.423  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.055   0.915  -0.945  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.310   1.110  -0.808  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.787   2.269  -1.359  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.089   0.183  -0.162  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.507  -0.977   0.370  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.854  -1.156   0.226  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.301  -1.890   1.012  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.676  -1.803   1.210  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.324  -3.071   0.669  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.894  -1.748   2.734  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.298  -0.595   0.658  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.662  -0.454   0.824  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.253   0.675   0.310  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.528   1.631  -0.342  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.175   2.853  -0.897  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.138   1.485  -0.510  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.545   0.364  -0.001  1.00  0.00           C  
HETATM   24  H1  UNL     1       7.799   0.642  -1.568  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.878   0.995   0.196  1.00  0.00           H  
HETATM   26  H3  UNL     1       7.626  -0.727  -0.406  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.504   0.078  -1.510  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.737   1.684  -0.638  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.544  -1.105   0.621  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.679   0.409   1.536  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.386  -0.356   1.545  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.530   1.218   0.694  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.404  -0.015  -1.511  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.240  -1.551  -0.614  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.699   1.630  -1.451  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.254   2.967  -1.836  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.265  -2.062   0.650  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.190  -2.825   0.009  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.646  -3.717   1.510  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.596  -3.637   0.061  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.736  -2.771   3.112  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.140  -1.092   3.180  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.933  -1.395   2.915  1.00  0.00           H  
HETATM   44  H21 UNL     1      -5.286  -1.172   1.329  1.00  0.00           H  
HETATM   45  H22 UNL     1      -6.337   0.848   0.409  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.463   3.692  -0.985  1.00  0.00           H  
HETATM   47  H24 UNL     1      -5.586   2.667  -1.916  1.00  0.00           H  
HETATM   48  H25 UNL     1      -5.997   3.170  -0.248  1.00  0.00           H  
HETATM   49  H26 UNL     1      -2.605   2.241  -1.019  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   12
CONECT    7    8   35
CONECT    8    9   10   10
CONECT    9   36
CONECT   10   11   23
CONECT   11   12   12   13
CONECT   12   37
CONECT   13   14
CONECT   14   15   16   17
CONECT   15   38   39   40
CONECT   16   41   42   43
CONECT   17   18   18   23
CONECT   18   19   44
CONECT   19   20   20   45
CONECT   20   21   22
CONECT   21   46   47   48
CONECT   22   23   23   49
END

HMDB0249590
     RDKit          3D
Cannabinol
 49 51  0  0  0  0  0  0  0  0999 V2000
    7.3852    0.3520   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9004    0.5953   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2757   -0.0298    0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779    0.1566    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895   -0.4528   -0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.2239   -0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    0.9147   -0.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    1.1097   -0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7868    2.2693   -1.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    0.1828   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5074   -0.9770    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -1.1561    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3005   -1.8896    1.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757   -1.8034    1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3244   -3.0710    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8943   -1.7483    2.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2980   -0.5949    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6624   -0.4544    0.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2529    0.6753    0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    1.6306   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1749    2.8532   -0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1378    1.4848   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5450    0.3637   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7987    0.6418   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8780    0.9948    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6263   -0.7274   -0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5037    0.0775   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7371    1.6836   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5442   -1.1054    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786    0.4090    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -0.3564    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298    1.2180    0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4036   -0.0145   -1.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399   -1.5505   -0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989    1.6295   -1.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    2.9672   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646   -2.0625    0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898   -2.8247    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6461   -3.7173    1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -3.6370    0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -2.7707    3.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1398   -1.0922    3.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9327   -1.3948    2.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2862   -1.1725    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3373    0.8476    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4626    3.6922   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5859    2.6673   -1.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9975    3.1697   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6047    2.2408   -1.0194 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12  6  1  0
 23 17  1  0
 23 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,6,9-Trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol	PhytoBank
3-Amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran	PhytoBank
CBN	PhytoBank

Chemical Formula

C₂₁H₂₆O₂

Average Molecular Weight

310.437

Monoisotopic Molecular Weight

310.193280077

IUPAC Name

6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen-1-ol

Traditional Name

cannabinol

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1

InChI Identifier

InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3

InChI Key

VBGLYOIFKLUMQG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Dibenzopyrans

Alternative Parents

Substituents

Dibenzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzopyran (CHEBI:3360 )
Other aromatic polyketides (C07580 )
Cannabinoids (C07580 )
Other aromatic polyketides (LMPK13120002 )

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	6.58	ALOGPS
logP	6.41	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.74 m³·mol⁻¹	ChemAxon
Polarizability	37.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	195.555	30932474
DeepCCS	[M-H]-	193.197	30932474
DeepCCS	[M-2H]-	227.038	30932474
DeepCCS	[M+Na]+	202.404	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.3	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	186.3	32859911
AllCCS	[M+Na-2H]-	186.5	32859911
AllCCS	[M+HCOO]-	186.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cannabinol	CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1	3228.3	Standard polar	33892256
Cannabinol	CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1	2525.8	Standard non polar	33892256
Cannabinol	CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1	2572.4	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 - Cannabinol GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cannabinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ugm-5190000000-4449dbc8fa340a46930a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cannabinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cannabinol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol NA , positive-QTOF	splash10-03k9-0197000000-02f99ed4da3fcd7169f3	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol Orbitrap 16V, negative-QTOF	splash10-0a4i-0009000000-863f2f390ccd9c8fe9cf	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol Orbitrap 21V, negative-QTOF	splash10-0a4i-0239000000-0e4f7fd6cc72c6827f66	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol Orbitrap 24V, negative-QTOF	splash10-004i-0493000000-413d38916c00ef6234a0	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol Orbitrap 30V, negative-QTOF	splash10-004i-0290000000-23fb1fb13cc8ffbba6bc	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-0a4i-0279000000-3fd78de5823f4e0b4e48	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-0006-0900000000-606aa97e25113b805228	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-014i-0090000000-499c21708d1be862ce18	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-014i-0090000000-392361b62c78f2977a9e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-0002-0900000000-7088a45fb84da09fea83	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-0udl-0890000000-c7254416b3809c79f5ad	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-004i-0090000000-58f6b8627e7b186b785c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-00dl-0590000000-1e1e1032320e700d9295	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol n/a 21V, negative-QTOF	splash10-004i-0090000000-bc7eaade0ce179bad040	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol QTOF 5V, positive-QTOF	splash10-03dj-0359000000-cc024dc534a3a9f9b62f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol QTOF 7V, positive-QTOF	splash10-03dj-0279000000-b3426208b22197d787ad	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol QTOF 10V, positive-QTOF	splash10-03dj-1298000000-931100d6611f22917d35	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol QTOF 15V, positive-QTOF	splash10-01vn-1292000000-998d4e1ea9b86bb2e35e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cannabinol QTOF 17V, positive-QTOF	splash10-01vp-2192000000-9babb635554716a06e4e	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannabinol 10V, Positive-QTOF	splash10-03di-0019000000-cc5908feb634826561a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannabinol 20V, Positive-QTOF	splash10-014i-4092000000-0d5f8eeb3c3657604c0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannabinol 40V, Positive-QTOF	splash10-0k96-9240000000-ad77015ae37c6f2204e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannabinol 10V, Negative-QTOF	splash10-0a4i-0009000000-4cb0ebdfaca0cd6a22d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannabinol 20V, Negative-QTOF	splash10-0a4i-0019000000-88786e42ff7bce36b197	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cannabinol 40V, Negative-QTOF	splash10-0006-3490000000-e6ffa5b4dc0e798b395b	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	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

C00002675

Chemspider ID

2447

KEGG Compound ID

C07580

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cannabinol

METLIN ID

Not Available

PubChem Compound

2543

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 Cannabinol (HMDB0249590)

MOL for HMDB0249590 (Cannabinol)

3D MOL for HMDB0249590 (Cannabinol)

3D SDF for HMDB0249590 (Cannabinol)

3D-SDF for HMDB0249590 (Cannabinol)

PDB for HMDB0249590 (Cannabinol)

3D PDB for HMDB0249590 (Cannabinol)

SMILES for HMDB0249590 (Cannabinol)

INCHI for HMDB0249590 (Cannabinol)

Structure for HMDB0249590 (Cannabinol)

3D Structure for HMDB0249590 (Cannabinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra