NP-MRD: Showing NP-Card for 3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol (NP0180960)

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Record Information

Version

2.0

Created at

2022-09-03 19:23:49 UTC

Updated at

2022-09-03 19:23:49 UTC

NP-MRD ID

NP0180960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol

Description

Cannabistilbene II belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol is found in Cannabis sativa. 3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol was first documented in 1984 (PMID: 6481358). Based on a literature review very few articles have been published on Cannabistilbene II.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032221232D          

 22 23  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    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
    0.0000   -4.1250    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC(O)=C1)\C=C\C1=CC=C(OC)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O5/c1-20-14-9-11(8-13(18)10-14)4-5-12-6-7-15(21-2)16(19)17(12)22-3/h4-7,9-11,18-19H,8H2,1-3H3/b5-4+

> <INCHI_KEY>
LIAAUPRCZCWDAE-SNAWJCMRSA-N

> <FORMULA>
C17H20O5

> <MOLECULAR_WEIGHT>
304.342

> <EXACT_MASS>
304.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.88889037692982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(E)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol

> <JCHEM_LOGP>
1.970625697333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.62897072024754

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.482500182885962

> <JCHEM_PKA_STRONGEST_BASIC>
-4.386206217272013

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
88.3985

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(E)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    5   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
2',3-Dihydroxy-3',4',5-trimethoxydihydrostilbene	MeSH
3,3'-Dihydroxy-2',4',5-trimethoxydihydrostilbene	MeSH

Chemical Formula

C₁₇H₂₀O₅

Average Mass

304.3420 Da

Monoisotopic Mass

304.13107 Da

IUPAC Name

3-[(E)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol

Traditional Name

3-[(E)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol

CAS Registry Number

Not Available

SMILES

COC1=CC(CC(O)=C1)\C=C\C1=CC=C(OC)C(O)=C1OC

InChI Identifier

InChI=1S/C17H20O5/c1-20-14-9-11(8-13(18)10-14)4-5-12-6-7-15(21-2)16(19)17(12)22-3/h4-7,9-11,18-19H,8H2,1-3H3/b5-4+

InChI Key

LIAAUPRCZCWDAE-SNAWJCMRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Enol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	1.97	ChemAxon
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.4 m³·mol⁻¹	ChemAxon
Polarizability	32.89 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4944274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

ElSohly HN, Ma GE, Turner CE, ElSohly MA: Constituents of Cannabis sativa, XXV. Isolation of two new dihydrostilbenes from a Panamanian variant. J Nat Prod. 1984 May-Jun;47(3):445-52. doi: 10.1021/np50033a008. [PubMed:6481358 ]
LOTUS database [Link]

Showing NP-Card for 3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol (NP0180960)

MOL for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

3D MOL for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

3D SDF for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

3D-SDF for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

PDB for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

3D PDB for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

SMILES for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

INCHI for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

Structure for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)

3D Structure for NP0180960 (3-[(1e)-2-(5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl)ethenyl]-2,6-dimethoxyphenol)