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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:43:06 UTC

Update Date

2021-09-26 23:00:55 UTC

HMDB ID

HMDB0249827

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cesamet

Description

Cesamet, also known as nabilone, belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Based on a literature review a significant number of articles have been published on Cesamet. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cesamet is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cesamet 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


  Mrv1652309112108432D          

 27 29  0  0  0  0            999 V2000
    8.5520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398    2.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5107    2.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
 10 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END

HMDB0249827
     RDKit          3D
Cesamet
 63 65  0  0  0  0  0  0  0  0999 V2000
    8.0647    0.9983   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7394   -0.4127    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853   -0.5588    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -0.1144   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9895   -0.3475    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    0.0435   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881   -0.2529    0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328    0.5559    1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -1.7434    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622    0.0390    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454    0.6215   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    0.8600   -1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4119    1.4554   -2.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.5131   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1368   -0.0715    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -0.3046    0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578   -0.4083    1.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3524    0.4828    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4391   -0.0753    1.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315    1.7955    1.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    0.6636   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8717   -0.3964   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156   -1.7454   -0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4035   -1.5999   -2.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1805   -2.5625   -2.8323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -0.2959   -2.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7462    0.7231   -1.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8635    1.4368    0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2271    1.6948   -0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4806    0.9990   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4760   -0.7480    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8535   -1.1094   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2166   -1.5937    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3460    0.0787    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -0.7005   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3391    0.9478   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781    0.3197    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -1.4133    0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8001    1.1288   -0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410   -0.5903   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    0.1130    2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1040    1.5577    1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802    0.6860    2.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508   -2.1126    1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776   -1.9138    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -2.2701    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.8930   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    1.7178   -3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7052   -0.7749    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3785    0.5377    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0937    0.1357    2.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5880   -1.1479    1.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    2.4553    1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4537    1.5434    2.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    2.2776    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    1.6238   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6360   -0.3834    0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3409   -0.1087   -1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0215   -2.4991   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4954   -1.9910   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622   -0.4893   -2.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4875    0.1206   -3.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7193    1.7168   -1.9022 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  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 16 10  1  0
 27 21  1  0
 27 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 11 47  1  0
 13 48  1  0
 16 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
 26 62  1  0
 27 63  1  0
M  END


  Mrv1652309112108432D          

 27 29  0  0  0  0            999 V2000
    8.5520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398    2.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5107    2.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
 10 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249827

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCC(C)(C)C1=CC2=C(C3CC(=O)CCC3C(C)(C)O2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3

> <INCHI_KEY>
GECBBEABIDMGGL-UHFFFAOYSA-N

> <FORMULA>
C24H36O3

> <MOLECULAR_WEIGHT>
372.549

> <EXACT_MASS>
372.266445019

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.971478401480084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one

> <ALOGPS_LOGP>
7.50

> <JCHEM_LOGP>
6.359703313333332

> <ALOGPS_LOGS>
-5.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.57023531728457

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.328192255940923

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890939401538866

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
110.202

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.93e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6aH,7H,8H,10H,10aH-benzo[c]isochromen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249827
     RDKit          3D
Cesamet
 63 65  0  0  0  0  0  0  0  0999 V2000
    8.0647    0.9983   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7394   -0.4127    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853   -0.5588    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -0.1144   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9895   -0.3475    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    0.0435   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881   -0.2529    0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328    0.5559    1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -1.7434    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622    0.0390    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454    0.6215   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    0.8600   -1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4119    1.4554   -2.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.5131   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1368   -0.0715    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -0.3046    0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578   -0.4083    1.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3524    0.4828    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4391   -0.0753    1.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315    1.7955    1.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    0.6636   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8717   -0.3964   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156   -1.7454   -0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4035   -1.5999   -2.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1805   -2.5625   -2.8323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -0.2959   -2.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7462    0.7231   -1.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8635    1.4368    0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2271    1.6948   -0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4806    0.9990   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4760   -0.7480    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8535   -1.1094   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2166   -1.5937    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3460    0.0787    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -0.7005   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3391    0.9478   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781    0.3197    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -1.4133    0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8001    1.1288   -0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410   -0.5903   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    0.1130    2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1040    1.5577    1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802    0.6860    2.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508   -2.1126    1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776   -1.9138    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -2.2701    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.8930   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    1.7178   -3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7052   -0.7749    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3785    0.5377    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0937    0.1357    2.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5880   -1.1479    1.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    2.4553    1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4537    1.5434    2.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    2.2776    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    1.6238   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6360   -0.3834    0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3409   -0.1087   -1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0215   -2.4991   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4954   -1.9910   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622   -0.4893   -2.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4875    0.1206   -3.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7193    1.7168   -1.9022 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  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 16 10  1  0
 27 21  1  0
 27 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 11 47  1  0
 13 48  1  0
 16 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
 26 62  1  0
 27 63  1  0
M  END

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      15.964  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.194  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.654  -1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.884  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.574   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.034   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.034  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.568   4.253   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.820   4.976   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.414  -1.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21   12                                                       
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   13   26   27                                                  
CONECT   26   25   10                                                       
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0249827
HETATM    1  C1  UNL     1       8.065   0.998  -0.320  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.739  -0.413   0.037  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.385  -0.559   0.636  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.256  -0.114  -0.281  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.989  -0.347   0.515  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.731   0.043  -0.255  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.588  -0.253   0.664  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.733   0.556   1.927  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.695  -1.743   1.016  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.262   0.039   0.089  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.045   0.621  -1.125  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.252   0.860  -1.597  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.412   1.455  -2.823  1.00  0.00           O  
HETATM   14  C13 UNL     1      -2.380   0.513  -0.852  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.137  -0.071   0.373  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.843  -0.305   0.833  1.00  0.00           C  
HETATM   17  O2  UNL     1      -3.258  -0.408   1.121  1.00  0.00           O  
HETATM   18  C16 UNL     1      -4.352   0.483   1.040  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.439  -0.075   1.932  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.931   1.795   1.660  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.823   0.664  -0.385  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.872  -0.396  -0.708  1.00  0.00           C  
HETATM   23  C21 UNL     1      -5.216  -1.745  -0.918  1.00  0.00           C  
HETATM   24  C22 UNL     1      -4.404  -1.600  -2.144  1.00  0.00           C  
HETATM   25  O3  UNL     1      -4.181  -2.563  -2.832  1.00  0.00           O  
HETATM   26  C23 UNL     1      -3.882  -0.296  -2.509  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.746   0.723  -1.407  1.00  0.00           C  
HETATM   28  H1  UNL     1       8.863   1.437   0.321  1.00  0.00           H  
HETATM   29  H2  UNL     1       7.227   1.695  -0.319  1.00  0.00           H  
HETATM   30  H3  UNL     1       8.481   0.999  -1.365  1.00  0.00           H  
HETATM   31  H4  UNL     1       8.476  -0.748   0.799  1.00  0.00           H  
HETATM   32  H5  UNL     1       7.854  -1.109  -0.823  1.00  0.00           H  
HETATM   33  H6  UNL     1       6.217  -1.594   1.009  1.00  0.00           H  
HETATM   34  H7  UNL     1       6.346   0.079   1.552  1.00  0.00           H  
HETATM   35  H8  UNL     1       5.275  -0.700  -1.223  1.00  0.00           H  
HETATM   36  H9  UNL     1       5.339   0.948  -0.497  1.00  0.00           H  
HETATM   37  H10 UNL     1       4.078   0.320   1.424  1.00  0.00           H  
HETATM   38  H11 UNL     1       3.982  -1.413   0.808  1.00  0.00           H  
HETATM   39  H12 UNL     1       2.800   1.129  -0.468  1.00  0.00           H  
HETATM   40  H13 UNL     1       2.741  -0.590  -1.162  1.00  0.00           H  
HETATM   41  H14 UNL     1       2.457   0.113   2.644  1.00  0.00           H  
HETATM   42  H15 UNL     1       2.104   1.558   1.646  1.00  0.00           H  
HETATM   43  H16 UNL     1       0.780   0.686   2.456  1.00  0.00           H  
HETATM   44  H17 UNL     1       0.651  -2.113   1.099  1.00  0.00           H  
HETATM   45  H18 UNL     1       2.278  -1.914   1.931  1.00  0.00           H  
HETATM   46  H19 UNL     1       2.115  -2.270   0.115  1.00  0.00           H  
HETATM   47  H20 UNL     1       0.912   0.893  -1.707  1.00  0.00           H  
HETATM   48  H21 UNL     1      -2.246   1.718  -3.295  1.00  0.00           H  
HETATM   49  H22 UNL     1      -0.705  -0.775   1.815  1.00  0.00           H  
HETATM   50  H23 UNL     1      -6.379   0.538   1.837  1.00  0.00           H  
HETATM   51  H24 UNL     1      -5.094   0.136   2.982  1.00  0.00           H  
HETATM   52  H25 UNL     1      -5.588  -1.148   1.850  1.00  0.00           H  
HETATM   53  H26 UNL     1      -4.784   2.455   1.832  1.00  0.00           H  
HETATM   54  H27 UNL     1      -3.454   1.543   2.643  1.00  0.00           H  
HETATM   55  H28 UNL     1      -3.146   2.278   1.034  1.00  0.00           H  
HETATM   56  H29 UNL     1      -5.381   1.624  -0.400  1.00  0.00           H  
HETATM   57  H30 UNL     1      -6.636  -0.383   0.059  1.00  0.00           H  
HETATM   58  H31 UNL     1      -6.341  -0.109  -1.669  1.00  0.00           H  
HETATM   59  H32 UNL     1      -6.021  -2.499  -1.019  1.00  0.00           H  
HETATM   60  H33 UNL     1      -4.495  -1.991  -0.091  1.00  0.00           H  
HETATM   61  H34 UNL     1      -2.862  -0.489  -2.967  1.00  0.00           H  
HETATM   62  H35 UNL     1      -4.488   0.121  -3.343  1.00  0.00           H  
HETATM   63  H36 UNL     1      -3.719   1.717  -1.902  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7   39   40
CONECT    7    8    9   10
CONECT    8   41   42   43
CONECT    9   44   45   46
CONECT   10   11   11   16
CONECT   11   12   47
CONECT   12   13   14   14
CONECT   13   48
CONECT   14   15   27
CONECT   15   16   16   17
CONECT   16   49
CONECT   17   18
CONECT   18   19   20   21
CONECT   19   50   51   52
CONECT   20   53   54   55
CONECT   21   22   27   56
CONECT   22   23   57   58
CONECT   23   24   59   60
CONECT   24   25   25   26
CONECT   26   27   61   62
CONECT   27   63
END

HMDB0249827
     RDKit          3D
Cesamet
 63 65  0  0  0  0  0  0  0  0999 V2000
    8.0647    0.9983   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7394   -0.4127    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853   -0.5588    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -0.1144   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9895   -0.3475    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313    0.0435   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881   -0.2529    0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328    0.5559    1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -1.7434    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622    0.0390    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454    0.6215   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    0.8600   -1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4119    1.4554   -2.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798    0.5131   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1368   -0.0715    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -0.3046    0.8331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578   -0.4083    1.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3524    0.4828    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4391   -0.0753    1.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315    1.7955    1.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    0.6636   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8717   -0.3964   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156   -1.7454   -0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4035   -1.5999   -2.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1805   -2.5625   -2.8323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -0.2959   -2.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7462    0.7231   -1.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8635    1.4368    0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2271    1.6948   -0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4806    0.9990   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4760   -0.7480    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8535   -1.1094   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2166   -1.5937    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3460    0.0787    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -0.7005   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3391    0.9478   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781    0.3197    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -1.4133    0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8001    1.1288   -0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410   -0.5903   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    0.1130    2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1040    1.5577    1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802    0.6860    2.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508   -2.1126    1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776   -1.9138    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -2.2701    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.8930   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    1.7178   -3.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7052   -0.7749    1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3785    0.5377    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0937    0.1357    2.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5880   -1.1479    1.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    2.4553    1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4537    1.5434    2.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    2.2776    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    1.6238   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6360   -0.3834    0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3409   -0.1087   -1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0215   -2.4991   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4954   -1.9910   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622   -0.4893   -2.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4875    0.1206   -3.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7193    1.7168   -1.9022 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  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 16 10  1  0
 27 21  1  0
 27 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 11 47  1  0
 13 48  1  0
 16 49  1  0
 19 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
 26 62  1  0
 27 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nabilone	MeSH
Nabilone, (6ar-trans)-isomer	MeSH
Nabilone, (6as-trans)-isomer	MeSH
Nabilone, (cis-(+-))-isomer	MeSH
Nabilone, (trans-(+-))-isomer	MeSH

Chemical Formula

C₂₄H₃₆O₃

Average Molecular Weight

372.549

Monoisotopic Molecular Weight

372.266445019

IUPAC Name

1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one

Traditional Name

1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6aH,7H,8H,10H,10aH-benzo[c]isochromen-9-one

CAS Registry Number

Not Available

SMILES

CCCCCCC(C)(C)C1=CC2=C(C3CC(=O)CCC3C(C)(C)O2)C(O)=C1

InChI Identifier

InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3

InChI Key

GECBBEABIDMGGL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ketone
Cyclic ketone
Ether
Oxacycle
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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)

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	7.5	ALOGPS
logP	6.36	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	110.2 m³·mol⁻¹	ChemAxon
Polarizability	44.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	213.411	30932474
DeepCCS	[M-H]-	210.686	30932474
DeepCCS	[M-2H]-	245.839	30932474
DeepCCS	[M+Na]+	222.13	30932474
AllCCS	[M+H]+	194.8	32859911
AllCCS	[M+H-H2O]+	192.2	32859911
AllCCS	[M+NH4]+	197.1	32859911
AllCCS	[M+Na]+	197.8	32859911
AllCCS	[M-H]-	200.8	32859911
AllCCS	[M+Na-2H]-	202.1	32859911
AllCCS	[M+HCOO]-	203.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cesamet	CCCCCCC(C)(C)C1=CC2=C(C3CC(=O)CCC3C(C)(C)O2)C(O)=C1	3419.4	Standard polar	33892256
Cesamet	CCCCCCC(C)(C)C1=CC2=C(C3CC(=O)CCC3C(C)(C)O2)C(O)=C1	2887.2	Standard non polar	33892256
Cesamet	CCCCCCC(C)(C)C1=CC2=C(C3CC(=O)CCC3C(C)(C)O2)C(O)=C1	2967.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cesamet,2TMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)C1CC(O[Si](C)(C)C)=CCC1C(C)(C)O2	2739.8	Semi standard non polar	33892256
Cesamet,2TMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)C1CC(O[Si](C)(C)C)=CCC1C(C)(C)O2	2802.1	Standard non polar	33892256
Cesamet,2TMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)C1CC(O[Si](C)(C)C)=CCC1C(C)(C)O2	3122.6	Standard polar	33892256
Cesamet,2TMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)C1C=C(O[Si](C)(C)C)CCC1C(C)(C)O2	2785.7	Semi standard non polar	33892256
Cesamet,2TMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)C1C=C(O[Si](C)(C)C)CCC1C(C)(C)O2	2824.8	Standard non polar	33892256
Cesamet,2TMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)C1C=C(O[Si](C)(C)C)CCC1C(C)(C)O2	3128.2	Standard polar	33892256
Cesamet,2TBDMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1CC(O[Si](C)(C)C(C)(C)C)=CCC1C(C)(C)O2	3198.6	Semi standard non polar	33892256
Cesamet,2TBDMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1CC(O[Si](C)(C)C(C)(C)C)=CCC1C(C)(C)O2	3160.8	Standard non polar	33892256
Cesamet,2TBDMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1CC(O[Si](C)(C)C(C)(C)C)=CCC1C(C)(C)O2	3314.3	Standard polar	33892256
Cesamet,2TBDMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1C=C(O[Si](C)(C)C(C)(C)C)CCC1C(C)(C)O2	3239.6	Semi standard non polar	33892256
Cesamet,2TBDMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1C=C(O[Si](C)(C)C(C)(C)C)CCC1C(C)(C)O2	3198.6	Standard non polar	33892256
Cesamet,2TBDMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1C=C(O[Si](C)(C)C(C)(C)C)CCC1C(C)(C)O2	3321.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cesamet GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4m-6069000000-b64348af18f99d83e132	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cesamet GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cesamet GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cesamet GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cesamet GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cesamet GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cesamet GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cesamet GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	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 - Cesamet 10V, Positive-QTOF	splash10-00di-0029000000-230312f8eb3e92648ded	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cesamet 20V, Positive-QTOF	splash10-00dj-9027000000-9c5048430fc4156d1839	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cesamet 40V, Positive-QTOF	splash10-0ac3-9111000000-ee81cbaf5b6622fe8fe7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cesamet 10V, Negative-QTOF	splash10-00di-0009000000-e7cb0fa6cccff516dcec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cesamet 20V, Negative-QTOF	splash10-00di-0009000000-e7cb0fa6cccff516dcec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cesamet 40V, Negative-QTOF	splash10-00kr-0079000000-da522a2b7bd19799eabd	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

36449

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nabilone

METLIN ID

Not Available

PubChem Compound

39860

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 Cesamet (HMDB0249827)

MOL for HMDB0249827 (Cesamet)

3D MOL for HMDB0249827 (Cesamet)

3D SDF for HMDB0249827 (Cesamet)

3D-SDF for HMDB0249827 (Cesamet)

PDB for HMDB0249827 (Cesamet)

3D PDB for HMDB0249827 (Cesamet)

SMILES for HMDB0249827 (Cesamet)

INCHI for HMDB0249827 (Cesamet)

Structure for HMDB0249827 (Cesamet)

3D Structure for HMDB0249827 (Cesamet)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra