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Showing NP-Card for Cannabicitran (NP0044862)

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Record Information
Version2.0
Created at2022-03-10 18:36:47 UTC
Updated at2022-03-10 22:18:49 UTC
NP-MRD IDNP0044862
Secondary Accession NumbersNone
Natural Product Identification
Common NameCannabicitran
DescriptionCannabicitran belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Cannabicitran possesses a tetracyclic skeleton, unique in the cannabinoid class of secondary metabolites. Interestingly, cannabicitran was first synthesized in 1971 (https://Doi.Org/10.1039/J39710000796) and later isolated from a natural cannabis source in 1974 (https://Doi.Org/10.1016/S0031-9422(00)91362-1) and its absolute configuration is still unknown (PMID: 6991645 ). No published data exists regarding cannabicitran’s biological or pharmacological activities. Cannabicitran is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://Doi.Org/10.1007/978-1-59259-947-9_2).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0044862 (Cannabicitran)


  Mrv1652307312018222D          

 25 28  0  0  1  0            999 V2000
   -3.8960   -0.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551    3.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2121    3.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859   -0.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0864   -0.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7419    1.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242    1.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7946    1.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    2.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742    0.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    1.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9323    1.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4404    1.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9354    2.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1742    2.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769    0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092    3.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0936    0.5027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5572    3.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2127    0.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091    2.4630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626    3.0070    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
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  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  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20 16  1  0  0  0  0
 21  4  1  1  0  0  0
 21 10  1  0  0  0  0
 21 13  1  0  0  0  0
 22 17  1  0  0  0  0
 22 20  1  0  0  0  0
 23 18  1  0  0  0  0
 23 21  1  0  0  0  0
 15 24  1  1  0  0  0
 16 25  1  6  0  0  0
M  END
Download

3D MOL for NP0044862 (Cannabicitran)

Download
3D SDF for NP0044862 (Cannabicitran)

  Mrv1652307312018222D          

 25 28  0  0  1  0            999 V2000
   -3.8960   -0.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551    3.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2121    3.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859   -0.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0864   -0.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7419    1.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242    1.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7946    1.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    2.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3742    0.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    1.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9323    1.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4404    1.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9354    2.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1742    2.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769    0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092    3.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0936    0.5027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5572    3.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2127    0.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091    2.4630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626    3.0070    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
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  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  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20 16  1  0  0  0  0
 21  4  1  1  0  0  0
 21 10  1  0  0  0  0
 21 13  1  0  0  0  0
 22 17  1  0  0  0  0
 22 20  1  0  0  0  0
 23 18  1  0  0  0  0
 23 21  1  0  0  0  0
 15 24  1  1  0  0  0
 16 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@]3(C)CC[C@]1([H])C(C)(C)OC1=C2C(O3)=CC(CCCCC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O2/c1-5-6-7-8-14-11-17-19-15-13-21(4,23-18(19)12-14)10-9-16(15)20(2,3)22-17/h11-12,15-16H,5-10,13H2,1-4H3/t15-,16-,21-/m0/s1

> <INCHI_KEY>
IXJXRDCCQRZSDV-QYWGDWMGSA-N

> <FORMULA>
C21H30O2

> <MOLECULAR_WEIGHT>
314.469

> <EXACT_MASS>
314.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.50886437946676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene

> <ALOGPS_LOGP>
7.01

> <JCHEM_LOGP>
5.621046758333332

> <ALOGPS_LOGS>
-6.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.581751103952252

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
93.86359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.75e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0044862 (Cannabicitran)
Download
PDB for NP0044862 (Cannabicitran)
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      -7.272  -1.346   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.023   6.402   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.263   7.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.640  -0.416   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.761  -1.050   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.262   0.406   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.751   0.702   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.251   2.159   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.085   3.705   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.217   2.033   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.221   3.920   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.698   1.285   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.367   1.952   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.740   2.455   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.689   3.285   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.613   4.429   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.325   4.252   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.890   1.451   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.249   2.980   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.630   5.745   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.908   0.938   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.040   5.679   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.264   0.440   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       1.884   4.598   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.597   5.613   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   14                                                       
CONECT    9   10   16                                                       
CONECT   10    9   21                                                       
CONECT   11   14   17                                                       
CONECT   12   14   18                                                       
CONECT   13   15   21                                                       
CONECT   14    8   11   12                                                  
CONECT   15   13   16   19   24                                             
CONECT   16    9   15   20   25                                             
CONECT   17   11   19   22                                                  
CONECT   18   12   19   23                                                  
CONECT   19   15   17   18                                                  
CONECT   20    2    3   16   22                                             
CONECT   21    4   10   13   23                                             
CONECT   22   17   20                                                       
CONECT   23   18   21                                                       
CONECT   24   15                                                            
CONECT   25   16                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

Download
3D PDB for NP0044862 (Cannabicitran)
Download
SMILES for NP0044862 (Cannabicitran)
[H][C@]12C[C@]3(C)CC[C@]1([H])C(C)(C)OC1=C2C(O3)=CC(CCCCC)=C1
Download
INCHI for NP0044862 (Cannabicitran)
InChI=1S/C21H30O2/c1-5-6-7-8-14-11-17-19-15-13-21(4,23-18(19)12-14)10-9-16(15)20(2,3)22-17/h11-12,15-16H,5-10,13H2,1-4H3/t15-,16-,21-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H30O2
Average Mass314.4690 Da
Monoisotopic Mass314.22458 Da
IUPAC Name(1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene
Traditional Name(1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene
CAS Registry NumberNot Available
SMILES
[H][C@]12C[C@]3(C)CC[C@]1([H])C(C)(C)OC1=C2C(O3)=CC(CCCCC)=C1
InChI Identifier
InChI=1S/C21H30O2/c1-5-6-7-8-14-11-17-19-15-13-21(4,23-18(19)12-14)10-9-16(15)20(2,3)22-17/h11-12,15-16H,5-10,13H2,1-4H3/t15-,16-,21-/m0/s1
InChI KeyIXJXRDCCQRZSDV-QYWGDWMGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cannabis sativaNULL
      Not Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.01ALOGPS
logP5.62ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.86 m³·mol⁻¹ChemAxon
Polarizability38.51 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound129360466  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References