NP-MRD: Showing NP-Card for 8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one (NP0220761)

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Record Information

Version

2.0

Created at

2022-09-05 22:09:58 UTC

Updated at

2022-09-05 22:09:58 UTC

NP-MRD ID

NP0220761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one

Description

8-Hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]Oct-3-en-2-one belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one is found in Nectandra amazonum. 8-Hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]Oct-3-en-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171510502D          

 30 32  0  0  0  0            999 V2000
   -2.1939    3.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4506    2.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    1.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6905    0.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4338    0.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706    1.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139    1.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955    1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840   -0.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255   -2.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7916    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2041   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    1.4699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208    1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255    2.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.3366    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END


  Mrv1533004171510502D          

 30 32  0  0  0  0            999 V2000
   -2.1939    3.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4506    2.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    1.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6905    0.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4338    0.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706    1.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139    1.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955    1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840   -0.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255   -2.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7916    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2041   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -0.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    1.4699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208    1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255    2.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.3366    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220761

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1C(C)C2(OC)C=C(CC=C)C(=O)C1(OC)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-8-9-14-12-22(29-6)13(2)18(23(30-7,20(14)24)21(22)25)15-10-16(26-3)19(28-5)17(11-15)27-4/h8,10-13,18,21,25H,1,9H2,2-7H3

> <INCHI_KEY>
IKLPDXKPWBONDW-UHFFFAOYSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.29389523657346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
2.6842648599999994

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.641252823977148

> <JCHEM_PKA_STRONGEST_BASIC>
-3.796519534357102

> <JCHEM_POLAR_SURFACE_AREA>
83.45

> <JCHEM_REFRACTIVITY>
112.33059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -4.095   5.998   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.708   5.330   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.593   3.794   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.205   3.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.090   1.591   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.362   0.723   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.750   1.391   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.022   0.524   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.410   1.192   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.865   2.927   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.253   3.595   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.525   2.728   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.297   0.922   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.297  -0.618   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.090  -1.286   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.501  -1.578   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.159  -3.079   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.288  -4.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.003  -1.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.671   0.152   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.211   0.152   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.981  -1.181   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.521  -1.181   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.003   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.963   2.744   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.501   1.883   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.159   3.384   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.288   4.431   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.934   0.152   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.399   0.628   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   26                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   19   29                                             
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   13   27   29                                             
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   16   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one

Traditional Name

8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1C(C)C2(OC)C=C(CC=C)C(=O)C1(OC)C2O

InChI Identifier

InChI=1S/C23H30O7/c1-8-9-14-12-22(29-6)13(2)18(23(30-7,20(14)24)21(22)25)15-10-16(26-3)19(28-5)17(11-15)27-4/h8,10-13,18,21,25H,1,9H2,2-7H3

InChI Key

IKLPDXKPWBONDW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nectandra amazonum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Cyclohexenone
Monocyclic benzene moiety
Cyclic alcohol
Secondary alcohol
Ketone
Ether
Dialkyl ether
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.72	ALOGPS
logP	2.68	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.64	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	112.33 m³·mol⁻¹	ChemAxon
Polarizability	44.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one (NP0220761)

MOL for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

3D MOL for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

3D SDF for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

3D-SDF for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

PDB for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

3D PDB for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

SMILES for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

INCHI for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

Structure for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)

3D Structure for NP0220761 (8-hydroxy-1,5-dimethoxy-6-methyl-3-(prop-2-en-1-yl)-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one)