NP-MRD: Showing NP-Card for (+/-)-cis-delta-9-THC (NP0139348)

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Record Information

Version

2.0

Created at

2022-06-29 19:50:24 UTC

Updated at

2022-06-29 19:50:24 UTC

NP-MRD ID

NP0139348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+/-)-cis-delta-9-THC

Description

6H-Dibenzo(b,d)pyran-1-ol, 6a-beta,7,8,10-a-beta-tetrahydro-3-pentyl-6,6,9-trimethyl-, (+-)-Z- belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Based on a literature review very few articles have been published on 6H-Dibenzo(b,d)pyran-1-ol, 6a-beta,7,8,10-a-beta-tetrahydro-3-pentyl-6,6,9-trimethyl-, (+-)-Z-.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    7.6543    0.3446   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1540    0.6691   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745   -0.3597   -1.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941   -0.1112   -1.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4327   -0.1442    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9821    0.0768    0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4218    1.3152    0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558    1.4137    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862    2.6700    1.0112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    0.3141    0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1986   -0.9273    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1782   -1.0453    0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0547   -2.0147    0.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368   -1.8878    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6319   -1.7326   -1.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946   -3.1803    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0052   -0.7410    1.0996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4573   -0.5576    0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8716    0.9022    0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0412    1.6196   -0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7021    2.4869   -1.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311    1.4231   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2179    0.5209    0.9837 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2134    1.2496   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9226   -0.4988    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7996    0.1116   -1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0316    1.6737   -0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8797    0.7360    0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294   -0.5019   -2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5378   -1.3521   -0.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228   -0.9438   -1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6293    0.8063   -1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    0.6128    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -1.1254    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885    2.1655    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374    3.5148    1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5658   -2.0495    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126   -2.1300   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4760   -2.3538   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681   -0.7039   -1.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -3.9410   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -3.5763    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922   -3.1331    0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9590   -1.0722    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5866   -0.8647   -0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1109   -1.1491    1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5673    1.3015    1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9410    0.9990    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8545    3.5214   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7005    2.0928   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1154    2.5406   -2.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816    1.9286   -0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558    1.0866    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  2  0
 20 21  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 14  1  0
 14 15  1  0
 14 16  1  0
 14 13  1  0
 13 11  1  0
 11 10  2  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  6 12  2  0
 17 23  1  0
 12 11  1  0
 10 23  1  0
 23 53  1  1
 22 52  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 19 47  1  0
 19 48  1  0
 18 45  1  0
 18 46  1  0
 17 44  1  1
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
  9 36  1  0
  7 35  1  0
  5 33  1  0
  5 34  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  2 27  1  0
  2 28  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 12 37  1  0
M  END


  Mrv1652306292221502D          

 25 27  0  0  1  0            999 V2000
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  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  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  2  0  0  0  0
 11 22  1  0  0  0  0
  6 23  1  1  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=C2C(O)=CC(CCCCC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m0/s1

> <INCHI_KEY>
CYQFCXCEBYINGO-DLBZAZTESA-N

> <FORMULA>
C21H30O2

> <MOLECULAR_WEIGHT>
314.469

> <EXACT_MASS>
314.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.6090839904426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR,10aS)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

> <ALOGPS_LOGP>
7.29

> <JCHEM_LOGP>
5.944157107333333

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.342429150192967

> <JCHEM_PKA_STRONGEST_BASIC>
-4.893304388168227

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
96.7335

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aR,10aS)-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.990  -4.260   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.990  -4.260   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   12                                             
CONECT    5    4                                                            
CONECT    6    4    7   23   24                                             
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   16   11                                                       
CONECT   23    6                                                            
CONECT   24    6   25                                                       
CONECT   25   24    2                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₂

Average Mass

314.4690 Da

Monoisotopic Mass

314.22458 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

[H][C@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=C2C(O)=CC(CCCCC)=C1

InChI Identifier

InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m0/s1

InChI Key

CYQFCXCEBYINGO-DLBZAZTESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21067

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22462

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+/-)-cis-delta-9-THC (NP0139348)

MOL for NP0139348 ((+/-)-cis-delta-9-THC)

3D MOL for NP0139348 ((+/-)-cis-delta-9-THC)

3D SDF for NP0139348 ((+/-)-cis-delta-9-THC)

3D-SDF for NP0139348 ((+/-)-cis-delta-9-THC)

PDB for NP0139348 ((+/-)-cis-delta-9-THC)

3D PDB for NP0139348 ((+/-)-cis-delta-9-THC)

SMILES for NP0139348 ((+/-)-cis-delta-9-THC)

INCHI for NP0139348 ((+/-)-cis-delta-9-THC)

Structure for NP0139348 ((+/-)-cis-delta-9-THC)

3D Structure for NP0139348 ((+/-)-cis-delta-9-THC)