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Showing NP-Card for (3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one (NP0218577)

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Record Information
Version2.0
Created at2022-09-05 19:16:52 UTC
Updated at2022-09-05 19:16:52 UTC
NP-MRD IDNP0218577
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one
DescriptionSCHEMBL13722333 belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. (3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one is found in Taxus cuspidata. Based on a literature review very few articles have been published on SCHEMBL13722333.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0218577 ((3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one)


  Mrv1652309052221162D          

 27 30  0  0  0  0            999 V2000
    9.0164    4.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8449    4.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0603    3.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    3.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1041    2.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4911    3.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7064    3.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    2.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0869    1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6744    0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2544    0.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  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
    6.6626    4.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4472    4.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6187    5.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4033    5.4567    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  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
Download

3D MOL for NP0218577 ((3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one)

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3D SDF for NP0218577 ((3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one)

  Mrv1652309052221162D          

 27 30  0  0  0  0            999 V2000
    9.0164    4.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8449    4.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0603    3.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    3.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1041    2.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4911    3.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7064    3.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    2.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0869    1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6744    0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2544    0.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  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
    6.6626    4.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4472    4.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6187    5.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4033    5.4567    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  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218577

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC2COC(=O)\C2=C/C2=CC=C3OCOC3=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O6/c1-23-17-5-3-13(9-19(17)24-2)7-15-11-25-21(22)16(15)8-14-4-6-18-20(10-14)27-12-26-18/h3-6,8-10,15H,7,11-12H2,1-2H3/b16-8-

> <INCHI_KEY>
GVNUFBXIXQNOCF-PXNMLYILSA-N

> <FORMULA>
C21H20O6

> <MOLECULAR_WEIGHT>
368.385

> <EXACT_MASS>
368.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.88039752312585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-3-[(2H-1,3-benzodioxol-5-yl)methylidene]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

> <JCHEM_LOGP>
3.688567656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.358424615221919

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
98.31540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-(2H-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0218577 ((3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one)
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PDB for NP0218577 ((3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one)
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      16.831   9.155   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.511   7.649   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.046   7.173   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.726   5.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.261   5.191   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.117   6.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.652   5.746   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.332   4.239   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.362   3.095   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.592   1.761   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.086   2.081   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.941   1.051   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.437   7.728   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.901   8.204   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.222   9.710   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.686  10.186   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24    6   25                                                       
CONECT   25   24    3   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

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3D PDB for NP0218577 ((3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one)
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SMILES for NP0218577 ((3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one)
COC1=CC=C(CC2COC(=O)\C2=C/C2=CC=C3OCOC3=C2)C=C1OC
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INCHI for NP0218577 ((3z)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one)
InChI=1S/C21H20O6/c1-23-17-5-3-13(9-19(17)24-2)7-15-11-25-21(22)16(15)8-14-4-6-18-20(10-14)27-12-26-18/h3-6,8-10,15H,7,11-12H2,1-2H3/b16-8-
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H20O6
Average Mass368.3850 Da
Monoisotopic Mass368.12599 Da
IUPAC Name(3Z)-3-[(2H-1,3-benzodioxol-5-yl)methylidene]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one
Traditional Name(3Z)-3-(2H-1,3-benzodioxol-5-ylmethylidene)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one
CAS Registry NumberNot Available
SMILES
COC1=CC=C(CC2COC(=O)\C2=C/C2=CC=C3OCOC3=C2)C=C1OC
InChI Identifier
InChI=1S/C21H20O6/c1-23-17-5-3-13(9-19(17)24-2)7-15-11-25-21(22)16(15)8-14-4-6-18-20(10-14)27-12-26-18/h3-6,8-10,15H,7,11-12H2,1-2H3/b16-8-
InChI KeyGVNUFBXIXQNOCF-PXNMLYILSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Taxus cuspidataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds  
Super ClassLignans, neolignans and related compounds  
ClassFuranoid lignans  
Sub ClassTetrahydrofuran lignans  
Direct ParentDibenzylbutyrolactone lignans  
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
    • 

  • Lignan lactone
    • 

  • O-dimethoxybenzene
    • 

  • Dimethoxybenzene
    • 

  • Benzodioxole
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Gamma butyrolactone
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Oxolane
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.69ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.32 m³·mol⁻¹ChemAxon
Polarizability37.88 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4479250  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5321541  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]