NP-MRD: Showing NP-Card for (2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one (NP0220583)

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Record Information

Version

2.0

Created at

2022-09-05 21:56:19 UTC

Updated at

2022-09-05 21:56:19 UTC

NP-MRD ID

NP0220583

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one

Description

(2R,3S,3aS)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one is found in Aniba taubertiana. Based on a literature review very few articles have been published on (2R,3S,3aS)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223562D          

 28 30  0  0  1  0            999 V2000
    3.2582    0.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    0.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    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
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    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
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   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  6  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  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 15 26  1  0  0  0  0
 14 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END


  Mrv1652309052223562D          

 28 30  0  0  1  0            999 V2000
    3.2582    0.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    0.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    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
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    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
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   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  6  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  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 15 26  1  0  0  0  0
 14 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0220583

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C[C@]2(CC=C)[C@H](C)[C@@H](OC2=CC1=O)C1=CC(OC)=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O6/c1-7-8-22-12-18(26-5)15(23)11-19(22)28-20(13(22)2)14-9-16(24-3)21(27-6)17(10-14)25-4/h7,9-13,20H,1,8H2,2-6H3/t13-,20-,22-/m1/s1

> <INCHI_KEY>
OKICALHDZHJOLZ-IIYZAJTGSA-N

> <FORMULA>
C22H26O6

> <MOLECULAR_WEIGHT>
386.444

> <EXACT_MASS>
386.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.50366781398386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,3aS)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

> <JCHEM_LOGP>
2.8948733360000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.207879431657586

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
108.47829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,3aS)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.082   1.278   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.675   1.904   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.429   0.999   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.400  -3.970   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.940  -3.970   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.710  -2.637   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.630   2.698   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12   27                                             
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                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   15                                                       
CONECT   27   14    4   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₆

Average Mass

386.4440 Da

Monoisotopic Mass

386.17294 Da

IUPAC Name

(2R,3S,3aS)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

Traditional Name

(2R,3S,3aS)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one

CAS Registry Number

Not Available

SMILES

COC1=C[C@]2(CC=C)[C@H](C)[C@@H](OC2=CC1=O)C1=CC(OC)=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C22H26O6/c1-7-8-22-12-18(26-5)15(23)11-19(22)28-20(13(22)2)14-9-16(24-3)21(27-6)17(10-14)25-4/h7,9-13,20H,1,8H2,2-6H3/t13-,20-,22-/m1/s1

InChI Key

OKICALHDZHJOLZ-IIYZAJTGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aniba taubertiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Benzofuran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Tetrahydrofuran
Cyclic ketone
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	2.89	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	108.48 m³·mol⁻¹	ChemAxon
Polarizability	40.5 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

162927335

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,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one (NP0220583)

MOL for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

3D MOL for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

3D SDF for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

3D-SDF for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

PDB for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

3D PDB for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

SMILES for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

INCHI for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

Structure for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)

3D Structure for NP0220583 ((2r,3s,3as)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one)