NP-MRD: Showing NP-Card for (2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one (NP0222358)

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Record Information

Version

2.0

Created at

2022-09-06 00:10:36 UTC

Updated at

2022-09-06 00:10:36 UTC

NP-MRD ID

NP0222358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one

Description

(2R,3S,3aR)-5,7-dimethoxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one 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. (2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one is found in Licaria chrysophylla. Based on a literature review very few articles have been published on (2R,3S,3aR)-5,7-dimethoxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202102D          

 29 32  0  0  1  0            999 V2000
    2.9268    4.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7553    3.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    2.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530    3.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6010    3.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8559    4.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039    5.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5588    5.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6629    4.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178    5.5223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2149    4.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0219    4.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5739    3.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    2.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204    2.0124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9920    1.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  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
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  1  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  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
M  END


  Mrv1652309062202102D          

 29 32  0  0  1  0            999 V2000
    2.9268    4.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7553    3.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684    2.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530    3.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6010    3.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8559    4.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039    5.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5588    5.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6629    4.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178    5.5223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2149    4.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0219    4.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5739    3.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    2.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204    2.0124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9920    1.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  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
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  1  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  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OCOC2=CC(=C1)[C@@H]1[C@@H](C)OC2=C(OC)C(=O)C(OC)=C[C@@]12CC=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O7/c1-6-7-22-10-16(25-4)18(23)20(26-5)21(22)29-12(2)17(22)13-8-14(24-3)19-15(9-13)27-11-28-19/h6,8-10,12,17H,1,7,11H2,2-5H3/t12-,17+,22+/m1/s1

> <INCHI_KEY>
OAOGZAWORNOYEF-WAQMSGSHSA-N

> <FORMULA>
C22H24O7

> <MOLECULAR_WEIGHT>
400.427

> <EXACT_MASS>
400.152203113

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.355457131913354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,3aR)-5,7-dimethoxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

> <JCHEM_LOGP>
2.193757853

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.202244268666128

> <JCHEM_POLAR_SURFACE_AREA>
72.45000000000002

> <JCHEM_REFRACTIVITY>
108.2684

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,3aR)-5,7-dimethoxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       5.463   7.975   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.143   6.469   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.288   5.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.752   5.914   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.722   7.059   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.198   8.523   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.167   9.668   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.643  11.133   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.704   8.844   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.180  10.308   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.734   7.699   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.241   8.019   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.271   6.875   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.259   6.235   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.029   4.901   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.998   3.756   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.318   2.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14   18                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    4   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    4   19                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   19                                                       
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₇

Average Mass

400.4270 Da

Monoisotopic Mass

400.15220 Da

IUPAC Name

(2R,3S,3aR)-5,7-dimethoxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

Traditional Name

(2R,3S,3aR)-5,7-dimethoxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one

CAS Registry Number

Not Available

SMILES

COC1=C2OCOC2=CC(=C1)[C@@H]1[C@@H](C)OC2=C(OC)C(=O)C(OC)=C[C@@]12CC=C

InChI Identifier

InChI=1S/C22H24O7/c1-6-7-22-10-16(25-4)18(23)20(26-5)21(22)29-12(2)17(22)13-8-14(24-3)19-15(9-13)27-11-28-19/h6,8-10,12,17H,1,7,11H2,2-5H3/t12-,17+,22+/m1/s1

InChI Key

OAOGZAWORNOYEF-WAQMSGSHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Licaria chrysophylla	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
Benzofuran
Anisole
Alkyl aryl ether
Benzenoid
Tetrahydrofuran
Vinylogous ester
Ketone
Cyclic ketone
Acetal
Ether
Oxacycle
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	2.19	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.27 m³·mol⁻¹	ChemAxon
Polarizability	41.36 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	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

162892356

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one (NP0222358)

MOL for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

3D MOL for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

3D SDF for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

3D-SDF for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

PDB for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

3D PDB for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

SMILES for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

INCHI for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

Structure for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)

3D Structure for NP0222358 ((2r,3s,3ar)-5,7-dimethoxy-3-(7-methoxy-2h-1,3-benzodioxol-5-yl)-2-methyl-3a-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one)