NP-MRD: Showing NP-Card for Cannabitwinol (NP0351482)

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Record Information

Version

2.0

Created at

2025-08-25 09:45:19 UTC

Updated at

2025-08-25 12:00:37 UTC

NP-MRD ID

NP0351482

Natural Product DOI

https://doi.org/10.57994/4529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabitwinol

Description

Cannabitwinol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Cannabitwinol was first documented in 2020 (PMID: 32880179). Based on a literature review very few articles have been published on Cannabitwinol (PMID: 39185742).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03012302562D          

 51 54  0  0  1  0            999 V2000
    0.7987   -0.1487    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   -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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    5.7158    0.8250    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3341    0.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764   -0.3219    0.0000 C   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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   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
    0.6085    0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  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
   -0.7145   -1.2375    0.0000 C   0  0  2  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
   -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
   -2.8579   -1.6500    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
   -1.4289   -0.8250    0.0000 H   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
    0.7537    0.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    0.6674    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  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  2  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
 16 15  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
 18 20  2  0  0  0  0
 17 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 16 25  1  0  0  0  0
 17 26  1  1  0  0  0
 16 27  1  6  0  0  0
  5 28  2  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
  2 39  1  0  0  0  0
 40 39  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 47 46  1  0  0  0  0
 40 47  1  0  0  0  0
 47 48  1  6  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
M  END


  Mrv2104 03012302562D          

 51 54  0  0  1  0            999 V2000
    0.7987   -0.1487    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   -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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    5.7158    0.8250    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3341    0.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764   -0.3219    0.0000 C   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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   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
    0.6085    0.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  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
   -0.7145   -1.2375    0.0000 C   0  0  2  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
   -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
   -2.8579   -1.6500    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
   -1.4289   -0.8250    0.0000 H   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
    0.7537    0.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    0.6674    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  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  2  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
 16 15  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
 18 20  2  0  0  0  0
 17 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 16 25  1  0  0  0  0
 17 26  1  1  0  0  0
 16 27  1  6  0  0  0
  5 28  2  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
  2 39  1  0  0  0  0
 40 39  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 47 46  1  0  0  0  0
 40 47  1  0  0  0  0
 47 48  1  6  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CCC(C)=C[C@@]1([H])C1=C(O)C=C(CCCCC)C(CC2=C(O)C(=C(O)C=C2CCCCC)[C@]2([H])C=C(C)CC[C@@]2([H])C(C)=C)=C1O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C43H60O4/c1-9-11-13-15-30-23-38(44)40(36-21-28(7)17-19-32(36)26(3)4)42(46)34(30)25-35-31(16-14-12-10-2)24-39(45)41(43(35)47)37-22-29(8)18-20-33(37)27(5)6/h21-24,32-33,36-37,44-47H,3,5,9-20,25H2,1-2,4,6-8H3/t32-,33-,36+,37+/m0/s1

> <INCHI_KEY>
UMJIRNQSAUOZKO-HEZKMHOLSA-N

> <FORMULA>
C43H60O4

> <MOLECULAR_WEIGHT>
640.949

> <EXACT_MASS>
640.449160412

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
78.1531686580907

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-({2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylphenyl}methyl)-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

> <JCHEM_LOGP>
12.768950464333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.963671097890068

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.322128661781024

> <JCHEM_PKA_STRONGEST_BASIC>
-5.694710624136862

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
200.74100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-({2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylphenyl}methyl)-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAR-23         0                                  
HETATM    1  O   UNK     0       0.965  -0.323   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.584   0.212   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.703  -0.601   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.136   0.161   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   41  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   42  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   48  H   UNK     0      -2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   49  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       1.407   0.626   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.905   1.246   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17   25   27                                             
CONECT   17   16   18   21   26                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16                                                       
CONECT   26   17                                                            
CONECT   27   16                                                            
CONECT   28    5   15   29                                                  
CONECT   29   28                                                            
CONECT   30    3   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   30   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2   40                                                  
CONECT   40   39   41   42   47                                             
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   40   48   49                                             
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  108    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₆₀O₄

Average Mass

640.9490 Da

Monoisotopic Mass

640.44916 Da

IUPAC Name

4-({2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylphenyl}methyl)-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

Traditional Name

4-({2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylphenyl}methyl)-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

CAS Registry Number

Not Available

SMILES

[H][C@]1(CCC(C)=C[C@@]1([H])C1=C(O)C=C(CCCCC)C(CC2=C(O)C(=C(O)C=C2CCCCC)[C@]2([H])C=C(C)CC[C@@]2([H])C(C)=C)=C1O)C(C)=C

InChI Identifier

InChI=1S/C43H60O4/c1-9-11-13-15-30-23-38(44)40(36-21-28(7)17-19-32(36)26(3)4)42(46)34(30)25-35-31(16-14-12-10-2)24-39(45)41(43(35)47)37-22-29(8)18-20-33(37)27(5)6/h21-24,32-33,36-37,44-47H,3,5,9-20,25H2,1-2,4,6-8H3/t32-,33-,36+,37+/m0/s1

InChI Key

UMJIRNQSAUOZKO-HEZKMHOLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	luca.pozzi@unimi.it	Università degli Studi di Milano	Luca Pozzi	2025-08-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	luca.pozzi@unimi.it	Università degli Studi di Milano	Luca Pozzi	2025-08-25	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Diphenylmethane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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
logP	12.77	ChemAxon
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	200.74 m³·mol⁻¹	ChemAxon
Polarizability	78.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162659880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shete SS, Mondal AK, Reddy DS: Total Synthesis of the Dimeric Phytocannabinoid Cannabitwinol (CBD Dimer) and Its Analogues. J Nat Prod. 2024 Sep 27;87(9):2255-2262. doi: 10.1021/acs.jnatprod.4c00674. Epub 2024 Aug 26. [PubMed:39185742 ]
Chianese G, Lopatriello A, Schiano-Moriello A, Caprioglio D, Mattoteia D, Benetti E, Ciceri D, Arnoldi L, De Combarieu E, Vitale RM, Amodeo P, Appendino G, De Petrocellis L, Taglialatela-Scafati O: Cannabitwinol, a Dimeric Phytocannabinoid from Hemp, Cannabis sativa L., Is a Selective Thermo-TRP Modulator. J Nat Prod. 2020 Sep 25;83(9):2727-2736. doi: 10.1021/acs.jnatprod.0c00668. Epub 2020 Sep 3. [PubMed:32880179 ]

Showing NP-Card for Cannabitwinol (NP0351482)

MOL for NP0351482 (Cannabitwinol)

3D MOL for NP0351482 (Cannabitwinol)

3D SDF for NP0351482 (Cannabitwinol)

3D-SDF for NP0351482 (Cannabitwinol)

PDB for NP0351482 (Cannabitwinol)

3D PDB for NP0351482 (Cannabitwinol)

SMILES for NP0351482 (Cannabitwinol)

INCHI for NP0351482 (Cannabitwinol)

Structure for NP0351482 (Cannabitwinol)

3D Structure for NP0351482 (Cannabitwinol)