NP-MRD: Showing NP-Card for Cannabinol-C4 (NP0044857)

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Record Information

Version

2.0

Created at

2022-03-10 18:36:42 UTC

Updated at

2022-03-10 22:19:19 UTC

NP-MRD ID

NP0044857

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabinol-C4

Description

Cannabinol-C4, also known as CBN-C4, belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Cannabinol-C4 also belongs to the class of cannabis compounds known as cannabinols or CBNs. The best known and most abundant CBN is cannabinol or cannabinol-C5 (CBN or CBN-C5). CBN has a 5-carbon aliphatic chain attached to its phenol group, while CBN-C4 has a 4-carbon aliphatic chain. Other CBNs have 1, 2 or 3 carbon atom chains. These shorter chain cannabinols are even less abundant than CBN-C5. Cannabinols are mildly psychoactive cannabinoids found only in trace amounts (PMID: 1221432 ) And are mostly found in aged cannabis (PMID:26870049 ). Pharmacologically relevant quantities are formed as a metabolite of tetrahydrocannabinol (THC) (PMID: 1140243 ). Cannabinols act as partial agonists of the CB1 receptors but tend to have higher affinities to CB2 receptors. The relative activity and CB1/CB2 affinity of CBN-C4 versus CBN-C5 has not been determined. Cannabinol-C4 is one of more than 120 cannabinoid compounds that can be found in cannabis plants (PMID: 6991645 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    6.3292   -0.4527   -1.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5181   -1.5979   -0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0492   -1.2959   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392   -0.0954   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    0.1103   -0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6575    0.8990   -1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2582    1.0695   -1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2896    1.8784   -1.9861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5481    0.4591   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0722   -0.3490    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -0.5070    0.8572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070   -0.9717    1.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0861   -0.8903    1.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -0.2265    3.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549   -2.2892    1.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072   -0.0273    0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0681    0.1110    0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7426    0.8983   -0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9947    1.5504   -0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7524    2.3868   -1.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    1.4298   -1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911    0.6406   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4185    0.3601   -0.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9119   -0.0996   -2.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3608   -0.8498   -1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6524   -2.4732   -1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8912   -1.8910    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676   -1.0776   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -2.1664   -0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0447   -0.3299    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    0.8294   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2129    1.4165   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2885    2.3302   -2.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8995   -1.1411    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4444   -0.3492    3.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2245    0.8728    3.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6607   -0.6023    3.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6203   -2.6774    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9672   -2.9134    2.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466   -2.3391    2.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6388   -0.4117    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8172    0.9923    0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1598    2.4488   -2.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7956    3.4199   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7636    1.9617   -2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1289    1.9598   -1.8041 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 22  2  0
 22 21  1  0
 21 19  2  0
 19 20  1  0
 19 18  1  0
 18 17  2  0
 10 11  2  0
 11  5  1  0
 22  9  1  0
 17 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  8 33  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 21 46  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 18 42  1  0
 17 41  1  0
 11 34  1  0
M  END


  Mrv1652307312018222D          

 22 24  0  0  0  0            999 V2000
   -3.3000    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    3.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    3.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 O   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  2  0  0  0  0
 13  2  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 15  1  0  0  0  0
 19 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20  3  1  0  0  0  0
 20  4  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 22 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044857

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h8-12,21H,5-7H2,1-4H3

> <INCHI_KEY>
GGVVJZIANMUEJO-UHFFFAOYSA-N

> <FORMULA>
C20H24O2

> <MOLECULAR_WEIGHT>
296.41

> <EXACT_MASS>
296.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.5698595095117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-butyl-6,6,9-trimethyl-6H-benzo[c]chromen-1-ol

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
5.968162358666666

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.318149474029278

> <JCHEM_PKA_STRONGEST_BASIC>
-4.922121772107328

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
91.13529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.85e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-butyl-6,6,9-trimethylbenzo[c]chromen-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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      -6.160   5.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   0.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.527   6.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.813   7.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.390   4.414   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.850   4.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.080   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.770   1.746   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   5.747   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.540   0.413   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.540   5.747   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   20                                                            
CONECT    4   20                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   14                                                       
CONECT    8    9   13                                                       
CONECT    9    8   16                                                       
CONECT   10   13   15                                                       
CONECT   11   14   17                                                       
CONECT   12   14   18                                                       
CONECT   13    2    8   10                                                  
CONECT   14    7   11   12                                                  
CONECT   15   10   16   19                                                  
CONECT   16    9   15   20                                                  
CONECT   17   11   19   21                                                  
CONECT   18   12   19   22                                                  
CONECT   19   15   17   18                                                  
CONECT   20    3    4   16   22                                             
CONECT   21   17                                                            
CONECT   22   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₂

Average Mass

296.4100 Da

Monoisotopic Mass

296.17763 Da

IUPAC Name

3-butyl-6,6,9-trimethyl-6H-benzo[c]chromen-1-ol

Traditional Name

3-butyl-6,6,9-trimethylbenzo[c]chromen-1-ol

CAS Registry Number

Not Available

SMILES

CCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1

InChI Identifier

InChI=1S/C20H24O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h8-12,21H,5-7H2,1-4H3

InChI Key

GGVVJZIANMUEJO-UHFFFAOYSA-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

Description

Belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Dibenzopyrans

Alternative Parents

Substituents

Dibenzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
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
logP	6.08	ALOGPS
logP	5.97	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.14 m³·mol⁻¹	ChemAxon
Polarizability	35.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

59444392

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cannabinol-C4 (NP0044857)

MOL for NP0044857 (Cannabinol-C4)

3D MOL for NP0044857 (Cannabinol-C4)

3D SDF for NP0044857 (Cannabinol-C4)

3D-SDF for NP0044857 (Cannabinol-C4)

PDB for NP0044857 (Cannabinol-C4)

3D PDB for NP0044857 (Cannabinol-C4)

SMILES for NP0044857 (Cannabinol-C4)

INCHI for NP0044857 (Cannabinol-C4)

Structure for NP0044857 (Cannabinol-C4)

3D Structure for NP0044857 (Cannabinol-C4)