NP-MRD: Showing NP-Card for 8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione (NP0317030)

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Record Information

Version

2.0

Created at

2022-09-11 16:38:03 UTC

Updated at

2022-09-11 16:38:04 UTC

NP-MRD ID

NP0317030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione

Description

8-(2H-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]Non-3-ene-2,7-dione belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. 8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione is found in Magnolia denudata. 8-(2H-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]Non-3-ene-2,7-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241513062D          

 26 29  0  0  0  0            999 V2000
    1.1947   -4.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5900   -3.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7735   -2.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191   -2.0665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191   -1.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -1.8483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7735   -0.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -1.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -2.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148   -2.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -1.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540    0.2335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757    1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6511    0.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197    0.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764   -0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779   -1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.3692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358   -1.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779   -2.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7608   -1.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1733   -2.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9983   -2.4720    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END


  Mrv1533004241513062D          

 26 29  0  0  0  0            999 V2000
    1.1947   -4.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5900   -3.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7735   -2.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191   -2.0665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191   -1.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -1.8483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7735   -0.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -1.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1285   -2.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148   -2.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -1.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540    0.2335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757    1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6511    0.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197    0.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764   -0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779   -1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.3692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358   -1.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779   -2.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7608   -1.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1733   -2.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9983   -2.4720    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0317030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC12OC(=O)C(C(C1C)C1=CC=C3OCOC3=C1)C(=O)C(CC=C)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O6/c1-4-5-13-9-20(23-3)11(2)16(17(18(13)21)19(22)26-20)12-6-7-14-15(8-12)25-10-24-14/h4,6-9,11,16-17H,1,5,10H2,2-3H3

> <INCHI_KEY>
CCGXHZFEGSPDIC-UHFFFAOYSA-N

> <FORMULA>
C20H20O6

> <MOLECULAR_WEIGHT>
356.374

> <EXACT_MASS>
356.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.550132719993265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(2H-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
3.827746279333333

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.084103872808658

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1953763162223385

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
93.0157

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(2H-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.230  -7.560   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.101  -6.512   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.444  -5.011   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.156  -3.857   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.156  -2.704   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.192  -3.450   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.444  -1.551   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.240  -2.511   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.240  -4.051   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.148  -4.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.148  -1.842   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.420  -2.710   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.807  -2.042   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.923  -0.506   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.141   0.436   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.621   1.886   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.082   1.840   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.650   0.361   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.263  -0.307   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.945  -1.893   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.906  -0.689   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.614  -3.281   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.945  -4.668   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.154  -3.281   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.924  -4.614   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.464  -4.614   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9   23                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   11                                                       
CONECT   20    7   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22    3                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₆

Average Mass

356.3740 Da

Monoisotopic Mass

356.12599 Da

IUPAC Name

8-(2H-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione

Traditional Name

8-(2H-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione

CAS Registry Number

Not Available

SMILES

COC12OC(=O)C(C(C1C)C1=CC=C3OCOC3=C1)C(=O)C(CC=C)=C2

InChI Identifier

InChI=1S/C20H20O6/c1-4-5-13-9-20(23-3)11(2)16(17(18(13)21)19(22)26-20)12-6-7-14-15(8-12)25-10-24-14/h4,6-9,11,16-17H,1,5,10H2,2-3H3

InChI Key

CCGXHZFEGSPDIC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Magnolia denudata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Ketal
Delta valerolactone
Delta_valerolactone
Oxane
Benzenoid
1,3-dicarbonyl compound
Carboxylic acid ester
Ketone
Lactone
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Hydrocarbon derivative
Aldehyde
Organic oxide
Carbonyl group
Organic oxygen compound
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	2.57	ALOGPS
logP	3.83	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.02 m³·mol⁻¹	ChemAxon
Polarizability	36.55 Å³	ChemAxon
Number of Rings	4	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

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-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione (NP0317030)

MOL for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

3D MOL for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

3D SDF for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

3D-SDF for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

PDB for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

3D PDB for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

SMILES for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

INCHI for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

Structure for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)

3D Structure for NP0317030 (8-(2h-1,3-benzodioxol-5-yl)-5-methoxy-9-methyl-3-(prop-2-en-1-yl)-6-oxabicyclo[3.2.2]non-3-ene-2,7-dione)