NP-MRD: Showing NP-Card for (2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one (NP0328535)

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Record Information

Version

2.0

Created at

2022-09-12 12:05:44 UTC

Updated at

2022-09-12 12:05:44 UTC

NP-MRD ID

NP0328535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one

Description

(2R,3S,3aS,7aS)-2-(1,3-Benzodioxole-5-yl)-2,3,3a,7a-tetrahydro-7a-hydroxy-3-methyl-3a-(2-propenyl)-7(4H)-benzofuranone 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,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one is found in Ocotea aciphylla. Based on a literature review very few articles have been published on (2R,3S,3aS,7aS)-2-(1,3-Benzodioxole-5-yl)-2,3,3a,7a-tetrahydro-7a-hydroxy-3-methyl-3a-(2-propenyl)-7(4H)-benzofuranone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122214052D          

 24 27  0  0  1  0            999 V2000
    5.6311    4.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8106    4.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    4.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    3.3400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3725    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975    2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    2.6255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7080    1.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204    2.0124    0.0000 O   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
    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
    4.1530    3.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5399    3.7205    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  1  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
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 13 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END


  Mrv1652309122214052D          

 24 27  0  0  1  0            999 V2000
    5.6311    4.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8106    4.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    4.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    3.3400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3725    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975    2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    2.6255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7080    1.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204    2.0124    0.0000 O   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
    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
    4.1530    3.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5399    3.7205    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  1  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
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 13 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H](O[C@]2(O)C(=O)C=CC[C@@]12CC=C)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O5/c1-3-8-18-9-4-5-16(20)19(18,21)24-17(12(18)2)13-6-7-14-15(10-13)23-11-22-14/h3-7,10,12,17,21H,1,8-9,11H2,2H3/t12-,17-,18+,19-/m1/s1

> <INCHI_KEY>
ZWZOJVXHAOTSDM-GBRSUSRYSA-N

> <FORMULA>
C19H20O5

> <MOLECULAR_WEIGHT>
328.364

> <EXACT_MASS>
328.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.74131028022762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,3aS,7aS)-2-(2H-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-7-one

> <JCHEM_LOGP>
3.847620131666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.75665750688913

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.963582564051517

> <JCHEM_PKA_STRONGEST_BASIC>
-4.259294912522463

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
88.03200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,3aS,7aS)-2-(2H-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2H-1-benzofuran-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.511   9.048   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.980   8.887   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.353   7.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.259   6.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.029   7.568   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.569   7.568   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.339   6.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.569   4.901   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.339   3.567   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.029   4.901   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.655   3.494   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.998   3.756   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.752   5.914   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.608   6.945   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10   23                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   13    4   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₅

Average Mass

328.3640 Da

Monoisotopic Mass

328.13107 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](O[C@]2(O)C(=O)C=CC[C@@]12CC=C)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C19H20O5/c1-3-8-18-9-4-5-16(20)19(18,21)24-17(12(18)2)13-6-7-14-15(10-13)23-11-22-14/h3-7,10,12,17,21H,1,8-9,11H2,2H3/t12-,17-,18+,19-/m1/s1

InChI Key

ZWZOJVXHAOTSDM-GBRSUSRYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ocotea aciphylla	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

Benzofuran
Benzodioxole
Cyclohexenone
Benzenoid
Tetrahydrofuran
Ketone
Hemiacetal
Oxacycle
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

15126691

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,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one (NP0328535)

MOL for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

3D MOL for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

3D SDF for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

3D-SDF for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

PDB for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

3D PDB for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

SMILES for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

INCHI for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

Structure for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

3D Structure for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)