NP-MRD: Showing NP-Card for Cannabistilbene IIa (NP0045206)

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Record Information

Version

2.0

Created at

2022-03-10 18:59:47 UTC

Updated at

2022-03-10 22:19:36 UTC

NP-MRD ID

NP0045206

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabistilbene IIa

Description

Cannabistilbene IIa is one of 3 cannabistilbenes (the others being cannabistilbene IIb and cannabistilbene I) found in Cannabis savita. It belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6) are derived from a common phenylpropene (C6-C3) skeleton building block. Cannabistilbene IIa belongs more formally to the class of the dihydrostilbenes. The introduction of one or more hydroxyl groups to a phenyl ring leads to stilbenoids. Stilbenoids were first detected and isolated from the stems of cannabis plants in 1982, from cannabis leaves in 1978 and from cannabis resin in 1986 (https://Doi.Org/10.1007/S11101-008-9094-4). Cannabistilbene IIa holds two hydroxyl groups (one is methylated) in ring A, both in a meta arrangement in relation to the C2 moiety. On the other hand, ring B holds one hydroxyl group in position 3 and two methoxyl groups in positions 2 and 4. Cannabistilbene IIa is a neutral, hydrophobic molecule that is insoluble in water. Cannabistilbene IIa is one of the non-cannabinoid phenolic compounds that are known to occur in the Cannabis plants (PMID: 28799497 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    6.0195    0.9613   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6856    1.4242   -0.3164 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872    0.5061   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -0.8101    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0078   -1.7535    0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3804   -3.0623    0.7333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011   -1.3413    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3413   -0.0199    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1137    0.3707    0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494    0.2283   -1.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713    0.6090   -1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    1.9175   -1.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253    2.3681   -1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8224    1.5239   -0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5319    0.2295   -0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5297   -0.6400   -0.1373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036   -0.2070   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870   -1.4951   -0.2409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440   -2.0035    1.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408    0.8848   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6944    1.8646   -0.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2569    0.2533   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2729    0.4489    0.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0350   -1.0997    0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -3.2805    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9303   -2.0558    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384    1.4519    0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6544   -0.1888    0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026    0.7813   -1.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -0.8461   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7374    2.5831   -1.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0568    3.3925   -1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8448    1.8917   -0.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4775   -0.2889   -0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -2.3966    1.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284   -2.8716    1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -1.2476    1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1040    1.9178   -0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 20  2  0
 20  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 17  2  0
 17 18  1  0
 18 19  1  0
 17 15  1  0
 15 16  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 12 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 20 38  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 16 34  1  0
 14 33  1  0
 13 32  1  0
 12 31  1  0
  7 26  1  0
  6 25  1  0
  4 24  1  0
M  END


  Mrv1652303202019012D          

 20 21  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    0.7145   -0.4125    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
    0.0000    0.8250    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
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  5  2  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19 14  1  0  0  0  0
 20  2  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045206

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCC2=C(OC)C(O)=CC=C2)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O4/c1-19-14-9-11(8-13(17)10-14)6-7-12-4-3-5-15(18)16(12)20-2/h3-5,8-10,17-18H,6-7H2,1-2H3

> <INCHI_KEY>
RSTDNUBRTQLVBF-UHFFFAOYSA-N

> <FORMULA>
C16H18O4

> <MOLECULAR_WEIGHT>
274.316

> <EXACT_MASS>
274.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.519952278556417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.5871353333333325

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.208394555970703

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.461704540521742

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5609925200372965

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
77.2844

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3   12                                                       
CONECT    5    3   15                                                       
CONECT    6    7   11                                                       
CONECT    7    6   12                                                       
CONECT    8   11   13                                                       
CONECT    9   11   14                                                       
CONECT   10   13   14                                                       
CONECT   11    6    8    9                                                  
CONECT   12    4    7   16                                                  
CONECT   13    8   10   17                                                  
CONECT   14    9   10   19                                                  
CONECT   15    5   16   18                                                  
CONECT   16   12   15   20                                                  
CONECT   17   13                                                            
CONECT   18   15                                                            
CONECT   19    1   14                                                       
CONECT   20    2   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₄

Average Mass

274.3160 Da

Monoisotopic Mass

274.12051 Da

IUPAC Name

3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol

Traditional Name

3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol

CAS Registry Number

Not Available

SMILES

COC1=CC(CCC2=C(OC)C(O)=CC=C2)=CC(O)=C1

InChI Identifier

InChI=1S/C16H18O4/c1-19-14-9-11(8-13(17)10-14)6-7-12-4-3-5-15(18)16(12)20-2/h3-5,8-10,17-18H,6-7H2,1-2H3

InChI Key

RSTDNUBRTQLVBF-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
Stemona cf. pierrei	Plant	KNApSAcK
Stemona collinsiae	Plant	KNApSAcK
Stemona japonica	Plant	KNApSAcK
Stemona pierrei	Plant	KNApSAcK
Stemona tuberosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.03	ALOGPS
logP	3.59	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.28 m³·mol⁻¹	ChemAxon
Polarizability	29.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0129945

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

642896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cannabistilbene IIa (NP0045206)

MOL for NP0045206 (Cannabistilbene IIa)

3D MOL for NP0045206 (Cannabistilbene IIa)

3D SDF for NP0045206 (Cannabistilbene IIa)

3D-SDF for NP0045206 (Cannabistilbene IIa)

PDB for NP0045206 (Cannabistilbene IIa)

3D PDB for NP0045206 (Cannabistilbene IIa)

SMILES for NP0045206 (Cannabistilbene IIa)

INCHI for NP0045206 (Cannabistilbene IIa)

Structure for NP0045206 (Cannabistilbene IIa)

3D Structure for NP0045206 (Cannabistilbene IIa)