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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014629

Secondary Accession Numbers

HMDB14629

Metabolite Identification

Common Name

Nabilone

Description

Nabilone is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It is a synthetic cannabinoid, which mimics the main ingredient of marijuana (THC) but it has more predictable side effects and causes no or minimal euphoria. Nabilone is not derived from the cannabis plant as is dronabinol. In Canada, the United States, the United Kingdom and Mexico, nabilone is marketed as Cesamet. It was approved in 1985 by the United States FDA for treatment of chemotherapy-induced nausea and vomiting that has not responded to conventional antiemetics. Though it was approved by the FDA in 1985, the drug only began marketing in the United States in 2006. It is also approved for use in treatment of anorexia and weight loss in patients with AIDS. Although it doesn't have the official indication (except in Mexico), nabilone is widely used as an adjunct therapy for chronic pain management. Numerous trials and case studies have demonstrate various benefits for condition such as fibromyalgia and multiple scerosis. Nabilone is a racemate consisting of the (S,S) and the (R,R) isomers ('trans').

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

486
  Mrv0541 02231214432D          

 29 31  0  0  1  0            999 V2000
    8.8492   -1.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5737    2.2512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4068    0.9851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5637   -0.2809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8492    0.1316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5637   -1.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3145    0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8360    0.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347   -0.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3211    0.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347   -1.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5769    1.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9762   -1.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3888   -1.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3973    0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368   -1.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6497   -1.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3973   -1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6497   -0.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240   -1.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3521   -2.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -0.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -1.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1328   -0.6153    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4183    0.4660    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  0  0  0  0
  2 12  2  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4 28  1  6  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 29  1  1  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  2  0  0  0  0
 10 12  1  0  0  0  0
 11 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0014629
     RDKit          3D
Nabilone
 63 65  0  0  0  0  0  0  0  0999 V2000
    7.4676   -0.1312   -0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1488   -0.7496   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085   -1.1811    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427   -0.0057    0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192    1.0642    0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    0.8016   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9284    0.4602    1.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    1.6705    2.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -0.7358    1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581    0.3940    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449    0.6266   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    0.5750   -1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851    0.8073   -2.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0272    0.2711   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8019    0.0313    0.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333    0.0925    1.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034   -0.2892    1.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9105   -1.0589    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0048   -1.3554    1.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197   -2.3489    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047   -0.1571   -0.2253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5878   -0.6483   -1.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1714    0.5617   -1.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1907    1.5674   -2.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934    2.3236   -3.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8396    1.7420   -1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771    0.2975   -1.2243 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7478   -0.4474    0.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2458   -0.4581   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4079    0.9713   -0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5152   -0.1386   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3664   -1.7039   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0943   -1.8581    0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5423   -1.7525   -0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -0.3992    1.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    0.4528    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9053    1.4564   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3942    1.9491    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8313    0.0299   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5586    1.7818   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111    1.5442    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.5955    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8576    1.7594    2.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142   -1.2473    2.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8324   -1.4508    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132   -0.4003    2.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1590    0.8638   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9774    0.7094   -3.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -0.0927    2.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8266   -1.9082    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2744   -0.4250    2.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5331   -2.0411    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139   -2.6378    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234   -3.2214    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083   -2.3948   -0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    0.7681    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1994   -1.3244   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3585   -1.1376   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8407    1.0538   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8423    0.2925   -2.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9692    2.1935   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1410    2.2667   -2.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4267   -0.2745   -2.1754 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  1
 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  6
M  END

486
  Mrv0541 02231214432D          

 29 31  0  0  1  0            999 V2000
    8.8492   -1.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5737    2.2512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4068    0.9851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5637   -0.2809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8492    0.1316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5637   -1.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3145    0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8360    0.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347   -0.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3211    0.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347   -1.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5769    1.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9762   -1.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3888   -1.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3973    0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368   -1.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6497   -1.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3973   -1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6497   -0.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240   -1.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3521   -2.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -0.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -1.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1328   -0.6153    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4183    0.4660    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  0  0  0  0
  2 12  2  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4 28  1  6  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 29  1  1  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  2  0  0  0  0
 10 12  1  0  0  0  0
 11 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014629

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC

> <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/t18-,19-/m1/s1

> <INCHI_KEY>
GECBBEABIDMGGL-RTBURBONSA-N

> <FORMULA>
C24H36O3

> <MOLECULAR_WEIGHT>
372.5408

> <EXACT_MASS>
372.266445018

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
44.91217962640465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR,10aR)-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>
9.32819225594924

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890939401546244

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
110.20200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.93e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nabilone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014629
     RDKit          3D
Nabilone
 63 65  0  0  0  0  0  0  0  0999 V2000
    7.4676   -0.1312   -0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1488   -0.7496   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085   -1.1811    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427   -0.0057    0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192    1.0642    0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    0.8016   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9284    0.4602    1.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    1.6705    2.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -0.7358    1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581    0.3940    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449    0.6266   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    0.5750   -1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851    0.8073   -2.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0272    0.2711   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8019    0.0313    0.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333    0.0925    1.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034   -0.2892    1.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9105   -1.0589    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0048   -1.3554    1.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197   -2.3489    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047   -0.1571   -0.2253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5878   -0.6483   -1.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1714    0.5617   -1.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1907    1.5674   -2.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934    2.3236   -3.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8396    1.7420   -1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771    0.2975   -1.2243 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7478   -0.4474    0.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2458   -0.4581   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4079    0.9713   -0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5152   -0.1386   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3664   -1.7039   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0943   -1.8581    0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5423   -1.7525   -0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -0.3992    1.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    0.4528    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9053    1.4564   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3942    1.9491    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8313    0.0299   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5586    1.7818   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111    1.5442    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.5955    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8576    1.7594    2.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142   -1.2473    2.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8324   -1.4508    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132   -0.4003    2.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1590    0.8638   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9774    0.7094   -3.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -0.0927    2.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8266   -1.9082    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2744   -0.4250    2.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5331   -2.0411    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139   -2.6378    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234   -3.2214    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083   -2.3948   -0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    0.7681    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1994   -1.3244   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3585   -1.1376   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8407    1.0538   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8423    0.2925   -2.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9692    2.1935   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1410    2.2667   -2.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4267   -0.2745   -2.1754 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  1
 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  6
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 486                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.519  -2.834   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      17.871   4.202   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.826   1.839   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      17.852  -0.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.519   0.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.852  -2.064   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.254   0.256   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.494   1.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.185  -0.524   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.266   1.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.185  -2.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.877   2.662   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.622  -3.398   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.392  -2.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.808   0.299   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082  -2.872   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.413  -2.096   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.808  -2.888   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.413  -0.492   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.751  -3.647   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.857  -4.202   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.307  -1.541   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415  -2.882   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.084  -3.657   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.747  -2.892   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.417  -3.667   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -2.902   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      18.915  -1.149   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      17.581   0.870   0.000  0.00  0.00           H+0
CONECT    1    6   11                                                       
CONECT    2   12                                                            
CONECT    3   15                                                            
CONECT    4    5    6    7   28                                             
CONECT    5    4    8    9   29                                             
CONECT    6    1    4   13   14                                             
CONECT    7    4   10                                                       
CONECT    8    5   12                                                       
CONECT    9    5   11   15                                                  
CONECT   10    7   12                                                       
CONECT   11    1    9   18                                                  
CONECT   12    2    8   10                                                  
CONECT   13    6                                                            
CONECT   14    6                                                            
CONECT   15    3    9   19                                                  
CONECT   16   17   20   21   22                                             
CONECT   17   16   18   19                                                  
CONECT   18   11   17                                                       
CONECT   19   15   17                                                       
CONECT   20   16   23                                                       
CONECT   21   16                                                            
CONECT   22   16                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0014629
HETATM    1  C1  UNL     1       7.468  -0.131  -0.846  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.149  -0.750  -1.188  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.409  -1.181   0.069  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.143  -0.006   0.980  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.319   1.064   0.396  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.928   0.802  -0.007  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.928   0.460   1.037  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.878   1.671   2.011  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.257  -0.736   1.851  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.558   0.394   0.467  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.345   0.627  -0.853  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.927   0.575  -1.442  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.085   0.807  -2.787  1.00  0.00           O  
HETATM   14  C13 UNL     1      -2.027   0.271  -0.623  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.802   0.031   0.716  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.533   0.092   1.255  1.00  0.00           C  
HETATM   17  O2  UNL     1      -2.903  -0.289   1.532  1.00  0.00           O  
HETATM   18  C16 UNL     1      -3.910  -1.059   0.831  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.005  -1.355   1.841  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.320  -2.349   0.400  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.405  -0.157  -0.225  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.588  -0.648  -1.028  1.00  0.00           C  
HETATM   23  C21 UNL     1      -6.171   0.562  -1.728  1.00  0.00           C  
HETATM   24  C22 UNL     1      -5.191   1.567  -2.144  1.00  0.00           C  
HETATM   25  O3  UNL     1      -5.493   2.324  -3.053  1.00  0.00           O  
HETATM   26  C23 UNL     1      -3.840   1.742  -1.540  1.00  0.00           C  
HETATM   27  C24 UNL     1      -3.377   0.298  -1.224  1.00  0.00           C  
HETATM   28  H1  UNL     1       7.748  -0.447   0.197  1.00  0.00           H  
HETATM   29  H2  UNL     1       8.246  -0.458  -1.572  1.00  0.00           H  
HETATM   30  H3  UNL     1       7.408   0.971  -0.903  1.00  0.00           H  
HETATM   31  H4  UNL     1       5.515  -0.139  -1.834  1.00  0.00           H  
HETATM   32  H5  UNL     1       6.366  -1.704  -1.739  1.00  0.00           H  
HETATM   33  H6  UNL     1       6.094  -1.858   0.620  1.00  0.00           H  
HETATM   34  H7  UNL     1       4.542  -1.753  -0.240  1.00  0.00           H  
HETATM   35  H8  UNL     1       4.880  -0.399   1.956  1.00  0.00           H  
HETATM   36  H9  UNL     1       6.176   0.453   1.138  1.00  0.00           H  
HETATM   37  H10 UNL     1       4.905   1.456  -0.499  1.00  0.00           H  
HETATM   38  H11 UNL     1       4.394   1.949   1.104  1.00  0.00           H  
HETATM   39  H12 UNL     1       2.831   0.030  -0.807  1.00  0.00           H  
HETATM   40  H13 UNL     1       2.559   1.782  -0.459  1.00  0.00           H  
HETATM   41  H14 UNL     1       2.611   1.544   2.823  1.00  0.00           H  
HETATM   42  H15 UNL     1       2.062   2.596   1.427  1.00  0.00           H  
HETATM   43  H16 UNL     1       0.858   1.759   2.438  1.00  0.00           H  
HETATM   44  H17 UNL     1       1.314  -1.247   2.199  1.00  0.00           H  
HETATM   45  H18 UNL     1       2.832  -1.451   1.284  1.00  0.00           H  
HETATM   46  H19 UNL     1       2.713  -0.400   2.820  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.159   0.864  -1.519  1.00  0.00           H  
HETATM   48  H21 UNL     1      -1.977   0.709  -3.220  1.00  0.00           H  
HETATM   49  H22 UNL     1      -0.381  -0.093   2.292  1.00  0.00           H  
HETATM   50  H23 UNL     1      -5.827  -1.908   1.389  1.00  0.00           H  
HETATM   51  H24 UNL     1      -5.274  -0.425   2.354  1.00  0.00           H  
HETATM   52  H25 UNL     1      -4.533  -2.041   2.604  1.00  0.00           H  
HETATM   53  H26 UNL     1      -2.414  -2.638   1.001  1.00  0.00           H  
HETATM   54  H27 UNL     1      -4.023  -3.221   0.536  1.00  0.00           H  
HETATM   55  H28 UNL     1      -3.008  -2.395  -0.658  1.00  0.00           H  
HETATM   56  H29 UNL     1      -4.804   0.768   0.327  1.00  0.00           H  
HETATM   57  H30 UNL     1      -5.199  -1.324  -1.845  1.00  0.00           H  
HETATM   58  H31 UNL     1      -6.358  -1.138  -0.421  1.00  0.00           H  
HETATM   59  H32 UNL     1      -6.841   1.054  -0.964  1.00  0.00           H  
HETATM   60  H33 UNL     1      -6.842   0.293  -2.567  1.00  0.00           H  
HETATM   61  H34 UNL     1      -3.969   2.194  -0.508  1.00  0.00           H  
HETATM   62  H35 UNL     1      -3.141   2.267  -2.146  1.00  0.00           H  
HETATM   63  H36 UNL     1      -3.427  -0.275  -2.175  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

HMDB0014629
     RDKit          3D
Nabilone
 63 65  0  0  0  0  0  0  0  0999 V2000
    7.4676   -0.1312   -0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1488   -0.7496   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4085   -1.1811    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427   -0.0057    0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192    1.0642    0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    0.8016   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9284    0.4602    1.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778    1.6705    2.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -0.7358    1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581    0.3940    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449    0.6266   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    0.5750   -1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851    0.8073   -2.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0272    0.2711   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8019    0.0313    0.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333    0.0925    1.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034   -0.2892    1.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9105   -1.0589    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0048   -1.3554    1.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197   -2.3489    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047   -0.1571   -0.2253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5878   -0.6483   -1.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1714    0.5617   -1.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1907    1.5674   -2.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934    2.3236   -3.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8396    1.7420   -1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771    0.2975   -1.2243 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7478   -0.4474    0.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2458   -0.4581   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4079    0.9713   -0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5152   -0.1386   -1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3664   -1.7039   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0943   -1.8581    0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5423   -1.7525   -0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -0.3992    1.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    0.4528    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9053    1.4564   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3942    1.9491    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8313    0.0299   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5586    1.7818   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111    1.5442    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.5955    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8576    1.7594    2.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142   -1.2473    2.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8324   -1.4508    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132   -0.4003    2.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1590    0.8638   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9774    0.7094   -3.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -0.0927    2.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8266   -1.9082    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2744   -0.4250    2.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5331   -2.0411    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139   -2.6378    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234   -3.2214    0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083   -2.3948   -0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    0.7681    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1994   -1.3244   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3585   -1.1376   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8407    1.0538   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8423    0.2925   -2.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9692    2.1935   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1410    2.2667   -2.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4267   -0.2745   -2.1754 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  1
 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  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cesamet	Kegg
Nabilone, (6ar-trans)-isomer	HMDB
Nabilone, (cis-(+-))-isomer	HMDB
Nabilone, (6as-trans)-isomer	HMDB
Nabilone, (trans-(+-))-isomer	HMDB
Lilly brand OF nabilone	HMDB

Chemical Formula

C₂₄H₃₆O₃

Average Molecular Weight

372.5408

Monoisotopic Molecular Weight

372.266445018

IUPAC Name

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

Traditional Name

nabilone

CAS Registry Number

51022-71-0

SMILES

[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC

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/t18-,19-/m1/s1

InChI Key

GECBBEABIDMGGL-RTBURBONSA-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

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014629)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00049 g/L	Not Available
LogP	6.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00049 g/L	ALOGPS
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	44.91 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
DarkChem	[M+H]+	191.206	31661259
DarkChem	[M-H]-	191.396	31661259
DeepCCS	[M-2H]-	232.13	30932474
DeepCCS	[M+Na]+	207.37	30932474
AllCCS	[M+H]+	194.8	32859911
AllCCS	[M+H-H2O]+	192.3	32859911
AllCCS	[M+NH4]+	197.2	32859911
AllCCS	[M+Na]+	197.9	32859911
AllCCS	[M-H]-	200.8	32859911
AllCCS	[M+Na-2H]-	202.2	32859911
AllCCS	[M+HCOO]-	203.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nabilone	[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC	3473.9	Standard polar	33892256
Nabilone	[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC	2930.6	Standard non polar	33892256
Nabilone	[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC	2924.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nabilone,1TMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1CC(=O)CC[C@H]1C(C)(C)O2	2678.4	Semi standard non polar	33892256
Nabilone,1TMS,isomer #2	CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CC=C(O[Si](C)(C)C)C[C@@H]21	2689.9	Semi standard non polar	33892256
Nabilone,1TMS,isomer #3	CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CCC(O[Si](C)(C)C)=C[C@@H]21	2683.8	Semi standard non polar	33892256
Nabilone,2TMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C)=CC[C@H]1C(C)(C)O2	2715.9	Semi standard non polar	33892256
Nabilone,2TMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C)=CC[C@H]1C(C)(C)O2	2826.0	Standard non polar	33892256
Nabilone,2TMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C)=CC[C@H]1C(C)(C)O2	3100.8	Standard polar	33892256
Nabilone,2TMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C)CC[C@H]1C(C)(C)O2	2739.3	Semi standard non polar	33892256
Nabilone,2TMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C)CC[C@H]1C(C)(C)O2	2830.8	Standard non polar	33892256
Nabilone,2TMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C)CC[C@H]1C(C)(C)O2	3112.1	Standard polar	33892256
Nabilone,1TBDMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1CC(=O)CC[C@H]1C(C)(C)O2	2891.6	Semi standard non polar	33892256
Nabilone,1TBDMS,isomer #2	CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CC=C(O[Si](C)(C)C(C)(C)C)C[C@@H]21	2934.3	Semi standard non polar	33892256
Nabilone,1TBDMS,isomer #3	CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CCC(O[Si](C)(C)C(C)(C)C)=C[C@@H]21	2913.7	Semi standard non polar	33892256
Nabilone,2TBDMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C(C)(C)C)=CC[C@H]1C(C)(C)O2	3177.5	Semi standard non polar	33892256
Nabilone,2TBDMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C(C)(C)C)=CC[C@H]1C(C)(C)O2	3185.3	Standard non polar	33892256
Nabilone,2TBDMS,isomer #1	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C(C)(C)C)=CC[C@H]1C(C)(C)O2	3302.4	Standard polar	33892256
Nabilone,2TBDMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)CC[C@H]1C(C)(C)O2	3181.8	Semi standard non polar	33892256
Nabilone,2TBDMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)CC[C@H]1C(C)(C)O2	3202.4	Standard non polar	33892256
Nabilone,2TBDMS,isomer #2	CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)CC[C@H]1C(C)(C)O2	3314.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nabilone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6s-4059000000-d86f1fa9d2fb7b5aeb43	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nabilone GC-MS (1 TMS) - 70eV, Positive	splash10-004i-9006500000-fa969e22f9069b4dae8c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nabilone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nabilone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 10V, Positive-QTOF	splash10-00di-0209000000-ae7db58f0d0bea9253a7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 20V, Positive-QTOF	splash10-007k-5309000000-fa6f8bf6ae3a68b350a9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 40V, Positive-QTOF	splash10-00kf-9142000000-06e05031e6b790e0575a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 10V, Negative-QTOF	splash10-00di-0009000000-93527ef802493b35cbc6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 20V, Negative-QTOF	splash10-00di-0139000000-9dff2b635e80d9a8a438	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 40V, Negative-QTOF	splash10-0671-4698000000-c6c6c7afb91f8c400cde	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 10V, Negative-QTOF	splash10-00di-0009000000-e7cb0fa6cccff516dcec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 20V, Negative-QTOF	splash10-00di-0009000000-d48b82525261ced239a6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 40V, Negative-QTOF	splash10-014i-0039000000-fc9aceb1067cf8a70471	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 10V, Positive-QTOF	splash10-00di-1009000000-89d93a87d01729ab9bc8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 20V, Positive-QTOF	splash10-008i-9216000000-0c92b93a021eea604013	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nabilone 40V, Positive-QTOF	splash10-0536-9101000000-910f891074aa1437ef37	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00486	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00486	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00486

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nabilone

METLIN ID

Not Available

PubChem Compound

5284592

PDB ID

Not Available

ChEBI ID

189797

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

Herman TS, Einhorn LH, Jones SE, Nagy C, Chester AB, Dean JC, Furnas B, Williams SD, Leigh SA, Dorr RT, Moon TE: Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy. N Engl J Med. 1979 Jun 7;300(23):1295-7. [PubMed:375088 ]
Cunningham D, Bradley CJ, Forrest GJ, Hutcheon AW, Adams L, Sneddon M, Harding M, Kerr DJ, Soukop M, Kaye SB: A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues. Eur J Cancer Clin Oncol. 1988 Apr;24(4):685-9. [PubMed:2838294 ]
Niiranen A, Mattson K: Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy. Am J Clin Oncol. 1987 Aug;10(4):325-9. [PubMed:3039831 ]
Einhorn LH, Nagy C, Furnas B, Williams SD: Nabilone: an effective antiemetic in patients receiving cancer chemotherapy. J Clin Pharmacol. 1981 Aug-Sep;21(8-9 Suppl):64S-69S. [PubMed:6271844 ]

Enzymes

Enzyme Details

1. Cannabinoid receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:: CNR1
Uniprot ID:: P21554
Molecular weight:: 52857.4

References

Davis M, Maida V, Daeninck P, Pergolizzi J: The emerging role of cannabinoid neuromodulators in symptom management. Support Care Cancer. 2007 Jan;15(1):63-71. Epub 2006 Dec 1. [PubMed:17139494 ]
Darmani NA: The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2. Eur J Pharmacol. 2001 Oct 26;430(1):49-58. [PubMed:11698062 ]
Hirst RA, Almond SL, Lambert DG: Characterisation of the rat cerebella CB1 receptor using SR141716A, a central cannabinoid receptor antagonist. Neurosci Lett. 1996 Dec 13;220(2):101-4. [PubMed:8981483 ]
Pertwee RG: Cannabis and cannabinoids: pharmacology and rationale for clinical use. Forsch Komplementarmed. 1999 Oct;6 Suppl 3:12-5. [PubMed:10575283 ]
Pertwee RG, Fernando SR: Evidence for the presence of cannabinoid CB1 receptors in mouse urinary bladder. Br J Pharmacol. 1996 Aug;118(8):2053-8. [PubMed:8864542 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Nabilone (HMDB0014629)

MOL for HMDB0014629 (Nabilone)

3D MOL for HMDB0014629 (Nabilone)

3D SDF for HMDB0014629 (Nabilone)

3D-SDF for HMDB0014629 (Nabilone)

PDB for HMDB0014629 (Nabilone)

3D PDB for HMDB0014629 (Nabilone)

SMILES for HMDB0014629 (Nabilone)

INCHI for HMDB0014629 (Nabilone)

Structure for HMDB0014629 (Nabilone)

3D Structure for HMDB0014629 (Nabilone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References