NP-MRD: Showing NP-Card for Cannabivarin (NP0044858)

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Record Information

Version

2.0

Created at

2022-03-10 18:36:43 UTC

Updated at

2022-03-10 22:19:38 UTC

NP-MRD ID

NP0044858

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabivarin

Description

Cannabivarin (CBV), also known as Cannabivarol, 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. CBV is considered a non-psychoactive cannabinoid. It does not produce the euphoric side effects found in THC. Minor amounts of CBV are found in the hemp varieties of Cannabis sativa. CBV 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 CBV has a 3-carbon aliphatic chain. Other CBNs have 1, 2 or 4 carbon atom chains. These shorter chain cannabinols are even less abundant than CBN-C5. CBV is an oxidation product of tetrahydrocannabivarin (THCV, THV). CBV 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

 43 45  0  0  0  0  0  0  0  0999 V2000
    6.2304   -0.8330    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7523   -0.7498    0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023   -0.7845   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5311   -0.7095   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236   -1.8074   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -1.6986   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -2.8696    0.0337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2043   -0.4409   -0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5718    0.6899   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517    0.5380   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0309    1.9409   -0.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    2.2599   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5180    3.1106    1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688    3.0378   -1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399    1.0437    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5008    1.2212    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3388    0.1419    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8609   -1.1449    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6867   -2.3573    0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4759   -1.3325    0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458   -0.2591    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8196   -1.2957    1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235   -1.4603   -0.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6594    0.1633    0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5884    0.2477    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4707   -1.5816    1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    0.0727   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -1.7354   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865   -2.7722   -0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494   -3.7717    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    1.4446   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    3.2023    1.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377    2.5770    2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941    4.1289    1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8780    3.1172   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2661    4.0089   -1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4767    2.4659   -2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9594    2.2096    0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4095    0.2974    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8767   -2.6209    1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2930   -3.2192   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6921   -2.1378    0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1333   -2.3373    0.2332 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 21  2  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
  9 10  2  0
 10  4  1  0
 21  8  1  0
 16 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  7 30  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 20 43  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 17 39  1  0
 16 38  1  0
 10 31  1  0
M  END


  Mrv1652307312018222D          

 21 23  0  0  0  0            999 V2000
   -2.8875    2.3645    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
   -2.0625    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
  8  7  2  0  0  0  0
 12  2  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  6  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18 14  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 21 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044858

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h7-11,20H,5-6H2,1-4H3

> <INCHI_KEY>
SVTKBAIRFMXQQF-UHFFFAOYSA-N

> <FORMULA>
C19H22O2

> <MOLECULAR_WEIGHT>
282.383

> <EXACT_MASS>
282.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.481578278971256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.61

> <JCHEM_LOGP>
5.523593693666667

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.318551965781628

> <JCHEM_PKA_STRONGEST_BASIC>
-4.922118860962297

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
86.53429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cannabivarin

> <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      -5.390   4.414   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      -3.850   4.414   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.770   1.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080   5.747   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.540   0.413   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.540   5.747   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   12                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    1    6                                                       
CONECT    6    5   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   15                                                       
CONECT    9   12   14                                                       
CONECT   10   13   16                                                       
CONECT   11   13   17                                                       
CONECT   12    2    7    9                                                  
CONECT   13    6   10   11                                                  
CONECT   14    9   15   18                                                  
CONECT   15    8   14   19                                                  
CONECT   16   10   18   20                                                  
CONECT   17   11   18   21                                                  
CONECT   18   14   16   17                                                  
CONECT   19    3    4   15   21                                             
CONECT   20   16                                                            
CONECT   21   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₂

Average Mass

282.3830 Da

Monoisotopic Mass

282.16198 Da

IUPAC Name

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

Traditional Name

cannabivarin

CAS Registry Number

33745-21-0

SMILES

CCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1

InChI Identifier

InChI=1S/C19H22O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h7-11,20H,5-6H2,1-4H3

InChI Key

SVTKBAIRFMXQQF-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
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	5.61	ALOGPS
logP	5.52	ChemAxon
logS	-4.9	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	2	ChemAxon
Refractivity	86.53 m³·mol⁻¹	ChemAxon
Polarizability	33.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

Cannabivarin

METLIN ID

Not Available

PubChem Compound

622545

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cannabivarin (NP0044858)

MOL for NP0044858 (Cannabivarin)

3D MOL for NP0044858 (Cannabivarin)

3D SDF for NP0044858 (Cannabivarin)

3D-SDF for NP0044858 (Cannabivarin)

PDB for NP0044858 (Cannabivarin)

3D PDB for NP0044858 (Cannabivarin)

SMILES for NP0044858 (Cannabivarin)

INCHI for NP0044858 (Cannabivarin)

Structure for NP0044858 (Cannabivarin)

3D Structure for NP0044858 (Cannabivarin)