NP-MRD: Showing NP-Card for Cannabichromevarin (NP0044835)

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Record Information

Version

2.0

Created at

2022-03-10 18:36:19 UTC

Updated at

2022-03-10 22:18:49 UTC

NP-MRD ID

NP0044835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabichromevarin

Description

Cannabichromevarin (CBCV) belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that include a 1-benzopyran moiety, a bicyclic structure made up of a benzene and a pyran ring fused together, so that the oxygen atom is at position one. Cannabichromevarin is a neutral compound. CBCV is the C3 analogue of cannabichromene (CBC) and bears structural similarity to other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBCV is a product of the decarboxylation of cannabichromevarinic acid (CBCVA), which occurs over time or after reaching temperatures above 90 ¬¨‚àûC. CBCVA is a product of the cyclization of cannabigerovarinic acid (CBGVA) (PMID: 30023762 ) (Https://Doi.Org/10.1016/B978-0-12-800756-3.00002-8). CBCV and its derivatives are as abundant as cannabinols in cannabis plants. CBCV is not psychoactive and is not scheduled by the Convention on Psychotropic Substances. CBCV is a propyl cannabinoid and an effective anticonvulsant used to treat brain cancer and epilepsy (https://En.Wikipedia.Org/wiki/Cannabichromevarin).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 48  0  0  0  0  0  0  0  0999 V2000
   -5.5732    0.1191    1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5946    0.8087    2.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -0.0167    2.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108   -0.3240    1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8930   -1.4645    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1681   -1.7285   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820   -2.8821   -1.3740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755   -0.8678   -1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9047    0.2704   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214    0.5285    0.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0759    1.1569   -0.8010 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570    0.9779   -1.9584 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5894    2.1558   -2.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123    0.9832   -1.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552   -0.2312   -0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9914   -0.1995   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3058   -0.1273    0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425   -0.0776    2.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7449   -0.0959    1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -0.2557   -2.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -1.1137   -2.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    0.0441    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8560   -0.8638    1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4987    0.7286    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0913    0.9303    3.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3547    1.8063    1.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6114   -0.9136    3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6907    0.6147    3.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6451   -2.1759    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0148   -3.1328   -2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3628    1.4458    1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044    3.0839   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4349    2.3008   -3.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257    1.9594   -3.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711    1.8929   -0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445    0.9393   -2.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301   -0.2123    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723   -1.1669   -1.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7664   -0.2356   -1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -1.0312    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356   -0.0033    3.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6122    0.8044    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941   -1.1053    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2857    0.5692    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9192    0.2918    2.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0977   -0.4423   -3.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920   -1.9914   -2.9257 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 21  1  0
 21 20  2  0
 20 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 17 19  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
 10  4  1  0
  9  8  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
 21 47  1  0
 20 46  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 10 31  1  0
M  END


  Mrv1652307312018212D          

 21 22  0  0  1  0            999 V2000
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9286    5.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232    4.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    3.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804    4.2450    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
    0.4323    2.8377    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    4.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
  5  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  6  1  0  0  0  0
 11  9  2  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14  8  2  0  0  0  0
 15  7  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  2  0  0  0  0
 18 16  1  0  0  0  0
 19  4  1  1  0  0  0
 19 10  1  6  0  0  0
 19 11  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC(O)=C2C=C[C@](C)(CCC=C(C)C)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O2/c1-5-7-15-12-17(20)16-9-11-19(4,21-18(16)13-15)10-6-8-14(2)3/h8-9,11-13,20H,5-7,10H2,1-4H3/t19-/m0/s1

> <INCHI_KEY>
AAXZFUQLLRMVOG-IBGZPJMESA-N

> <FORMULA>
C19H26O2

> <MOLECULAR_WEIGHT>
286.415

> <EXACT_MASS>
286.193280077

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.094060155564094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromen-5-ol

> <ALOGPS_LOGP>
5.97

> <JCHEM_LOGP>
5.710530620666665

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.467095996379024

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9148926829703425

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
90.40109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propylchromen-5-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      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.733  10.551   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.777   8.836   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.183   3.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.797   6.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.270   7.924   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.807   5.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.260   9.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   19                                                            
CONECT    5    1    7                                                       
CONECT    6    8   10                                                       
CONECT    7    5   15                                                       
CONECT    8    6   14                                                       
CONECT    9   11   16                                                       
CONECT   10    6   19                                                       
CONECT   11    9   19                                                       
CONECT   12   15   17                                                       
CONECT   13   15   18                                                       
CONECT   14    2    3    8                                                  
CONECT   15    7   12   13                                                  
CONECT   16    9   17   18                                                  
CONECT   17   12   16   20                                                  
CONECT   18   13   16   21                                                  
CONECT   19    4   10   11   21                                             
CONECT   20   17                                                            
CONECT   21   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₂

Average Mass

286.4150 Da

Monoisotopic Mass

286.19328 Da

IUPAC Name

(2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromen-5-ol

Traditional Name

(2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propylchromen-5-ol

CAS Registry Number

41408-19-9

SMILES

CCCC1=CC(O)=C2C=C[C@](C)(CCC=C(C)C)OC2=C1

InChI Identifier

InChI=1S/C19H26O2/c1-5-7-15-12-17(20)16-9-11-19(4,21-18(16)13-15)10-6-8-14(2)3/h8-9,11-13,20H,5-7,10H2,1-4H3/t19-/m0/s1

InChI Key

AAXZFUQLLRMVOG-IBGZPJMESA-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 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

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
logP	5.97	ALOGPS
logP	5.71	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.47	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	5	ChemAxon
Refractivity	90.4 m³·mol⁻¹	ChemAxon
Polarizability	34.09 Å³	ChemAxon
Number of Rings	2	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

139496813

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cannabichromevarin (NP0044835)

MOL for NP0044835 (Cannabichromevarin)

3D MOL for NP0044835 (Cannabichromevarin)

3D SDF for NP0044835 (Cannabichromevarin)

3D-SDF for NP0044835 (Cannabichromevarin)

PDB for NP0044835 (Cannabichromevarin)

3D PDB for NP0044835 (Cannabichromevarin)

SMILES for NP0044835 (Cannabichromevarin)

INCHI for NP0044835 (Cannabichromevarin)

Structure for NP0044835 (Cannabichromevarin)

3D Structure for NP0044835 (Cannabichromevarin)