NP-MRD: Showing NP-Card for 4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one (NP0189994)

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Record Information

Version

2.0

Created at

2022-09-04 06:35:18 UTC

Updated at

2022-09-04 06:35:19 UTC

NP-MRD ID

NP0189994

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one

Description

4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(2H-1,3-benzodioxol-5-yl)methylidene]oxolan-2-one belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. 4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one is found in Chamaecyparis formosensis, Chamaecyparis obtusa, Juniperus chinensis, Juniperus communis, Juniperus horizontalis, Juniperus rigida, Juniperus thurifera, Linum corymbulosum, Micranthemum umbrosum, Pterocarpus santalinus, Taiwania cryptomerioides and Zanthoxylum nitidum. 4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(2H-1,3-benzodioxol-5-yl)methylidene]oxolan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04121516532D          

 26 30  0  0  0  0            999 V2000
    2.6147    3.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6543    4.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188    3.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    3.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9604    4.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5735    5.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3581    5.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0726    5.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6857    4.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3501    4.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5296    4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9165    3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    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
    1.1387    0.8555    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    2.1904    0.0000 O   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  2  2  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
  5 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
M  END


  Mrv0541 04121516532D          

 26 30  0  0  0  0            999 V2000
    2.6147    3.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6543    4.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188    3.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    3.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9604    4.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5735    5.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3581    5.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0726    5.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6857    4.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3501    4.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5296    4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9165    3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    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
    1.1387    0.8555    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    2.1904    0.0000 O   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  2  2  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
  5 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0189994

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1OCC(CC2=CC=C3OCOC3=C2)C1=CC1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,6-8,14H,5,9-11H2

> <INCHI_KEY>
CMJGAYUQSLJSCR-UHFFFAOYSA-N

> <FORMULA>
C20H16O6

> <MOLECULAR_WEIGHT>
352.342

> <EXACT_MASS>
352.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.41767128563056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
3.6271436550000002

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4391065326307215

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
91.15590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2H-1,3-benzodioxol-5-ylmethyl)-3-(2H-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  O   UNK     0       4.881   6.352   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.345   6.828   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.821   8.293   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.361   8.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.837   6.828   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.302   6.352   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.446   7.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.126   8.889   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.270   9.919   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.735   9.444   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.069  10.214   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      16.213   9.183   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.587   7.776   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.055   7.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.911   6.907   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590   2.073   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       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+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
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14    7                                                       
CONECT   16    5    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   18                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₆

Average Mass

352.3420 Da

Monoisotopic Mass

352.09469 Da

IUPAC Name

4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(2H-1,3-benzodioxol-5-yl)methylidene]oxolan-2-one

Traditional Name

4-(2H-1,3-benzodioxol-5-ylmethyl)-3-(2H-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one

CAS Registry Number

Not Available

SMILES

O=C1OCC(CC2=CC=C3OCOC3=C2)C1=CC1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C20H16O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,6-8,14H,5,9-11H2

InChI Key

CMJGAYUQSLJSCR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chamaecyparis formosensis	LOTUS Database	35616633
Chamaecyparis obtusa	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Juniperus horizontalis	LOTUS Database	35616633
Juniperus rigida	LOTUS Database	35616633
Juniperus thurifera	LOTUS Database	35616633
Linum corymbulosum	LOTUS Database	35616633
Micranthemum umbrosum	LOTUS Database	35616633
Pterocarpus santalinus	LOTUS Database	35616633
Taiwania cryptomerioides	LOTUS Database	35616633
Zanthoxylum nitidum	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Benzodioxole
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
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	2.82	ALOGPS
logP	3.63	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.16 m³·mol⁻¹	ChemAxon
Polarizability	35.42 Å³	ChemAxon
Number of Rings	5	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

98946

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one (NP0189994)

MOL for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

3D MOL for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

3D SDF for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

3D-SDF for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

PDB for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

3D PDB for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

SMILES for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

INCHI for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

Structure for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)

3D Structure for NP0189994 (4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)oxolan-2-one)