NP-MRD: Showing NP-Card for Cannabidiol-C4 (NP0044839)

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Record Information

Version

2.0

Created at

2022-03-10 18:36:23 UTC

Updated at

2022-03-10 22:18:58 UTC

NP-MRD ID

NP0044839

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabidiol-C4

Description

Cannabidiol-C4 is the butyl analogue of cannabidiol, which is one of the main phytocannabinoids found in Cannabis sativa (PMID: 6991645 ). Cannabidiol-C4 is a resorcinol, which has a meta arrangement of its two hydroxyl groups on the benzene ring. Because of the mixed biosynthetic origins of cannabidiol-C4, it can be considered as a polyketide and a monoterpenoid (DOI: 10.1016/B978-0-12-800756-3.00002-8). Cannabidiol-C4 is a neutral compound. Unlike CBD, research regarding the pharmacological properties of cannabidiol-C4 is scarce.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 51  0  0  0  0  0  0  0  0999 V2000
   -4.0526    1.8965   -2.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155    1.0903   -1.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721    1.0678   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5299    0.3320   -1.1402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7201   -1.0976   -1.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6949   -1.9728   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233   -1.1812    1.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4931   -1.9115    2.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    0.0588    1.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680    0.7766    0.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3634    0.6255    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892    1.5747   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1428    2.5094   -1.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8384    1.6010   -0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    0.6667    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9227    0.7123    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443   -0.1918   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478   -0.1310    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8132   -1.0813   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -0.2823    1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2704   -0.2939    0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522   -1.3158    1.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9379    2.4926   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415    1.9831   -3.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8231    1.5425   -0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5915    1.7292    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1736    0.1026    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279    0.7403   -2.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443   -1.5519   -2.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7599   -1.2266   -1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432   -2.5378   -0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4788   -2.7432   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775   -2.7385    2.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556   -1.2497    3.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4579   -2.3409    1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    0.5458    2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0359    1.8651    0.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3609    3.2280   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4540    2.3680   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3146    1.7629    0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0950    0.3499    1.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4556   -0.0544   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3525   -1.2396    0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4545    0.9343   -0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3867   -0.3724    1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8163   -1.3975   -0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2621   -2.0361   -0.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9351   -0.5759   -1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1504   -1.0314    1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0890   -2.0002    2.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 15 20  1  0
 20 21  2  0
 21 22  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 10  4  1  0
 21 11  1  0
  4 28  1  6
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  1
 13 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 22 50  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652307312018212D          

 24 25  0  0  1  0            999 V2000
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
   -1.4289    4.9500    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
    0.7145    4.5375    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
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789    5.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 13  2  2  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  6  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  2  0  0  0  0
 17 20  1  1  0  0  0
 20 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 16 23  1  1  0  0  0
 17 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044839

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CCC(C)=C[C@@]1([H])C1=C(O)C=C(CCCC)C=C1O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-5-6-7-15-11-18(21)20(19(22)12-15)17-10-14(4)8-9-16(17)13(2)3/h10-12,16-17,21-22H,2,5-9H2,1,3-4H3/t16-,17+/m0/s1

> <INCHI_KEY>
WBRXESQKGXYDOL-DLBZAZTESA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.115462223420145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-butyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol

> <ALOGPS_LOGP>
5.63

> <JCHEM_LOGP>
5.880632461666667

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.583829721690675

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.128748513501401

> <JCHEM_PKA_STRONGEST_BASIC>
-5.723974393445297

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
93.92989999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-butyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JUL-20         0                                  
HETATM    1  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.707   9.877   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       2.667   7.700   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.000   7.700   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   15                                                       
CONECT    8    9   14                                                       
CONECT    9    8   16                                                       
CONECT   10   14   17                                                       
CONECT   11   15   18                                                       
CONECT   12   15   19                                                       
CONECT   13    2    3   16                                                  
CONECT   14    4    8   10                                                  
CONECT   15    7   11   12                                                  
CONECT   16    9   13   17   23                                             
CONECT   17   10   16   20   24                                             
CONECT   18   11   20   21                                                  
CONECT   19   12   20   22                                                  
CONECT   20   17   18   19                                                  
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4420 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

5-butyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol

Traditional Name

5-butyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

[H][C@]1(CCC(C)=C[C@@]1([H])C1=C(O)C=C(CCCC)C=C1O)C(C)=C

InChI Identifier

InChI=1S/C20H28O2/c1-5-6-7-15-11-18(21)20(19(22)12-15)17-10-14(4)8-9-16(17)13(2)3/h10-12,16-17,21-22H,2,5-9H2,1,3-4H3/t16-,17+/m0/s1

InChI Key

WBRXESQKGXYDOL-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	NULL	Not Available

Chemical Taxonomy

Classification

Not classified

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	5.63	ALOGPS
logP	5.88	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.93 m³·mol⁻¹	ChemAxon
Polarizability	36.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

59444413

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cannabidiol-C4 (NP0044839)

MOL for NP0044839 (Cannabidiol-C4)

3D MOL for NP0044839 (Cannabidiol-C4)

3D SDF for NP0044839 (Cannabidiol-C4)

3D-SDF for NP0044839 (Cannabidiol-C4)

PDB for NP0044839 (Cannabidiol-C4)

3D PDB for NP0044839 (Cannabidiol-C4)

SMILES for NP0044839 (Cannabidiol-C4)

INCHI for NP0044839 (Cannabidiol-C4)

Structure for NP0044839 (Cannabidiol-C4)

3D Structure for NP0044839 (Cannabidiol-C4)