NP-MRD: Showing NP-Card for (4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one (NP0313324)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 10:46:57 UTC

Updated at

2022-09-11 10:46:57 UTC

NP-MRD ID

NP0313324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one

Description

(4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]Dodeca-1(9),2(6),7,11-tetraen-5-one belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). (4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one is found in Lonchocarpus castilloi. Based on a literature review very few articles have been published on (4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]Dodeca-1(9),2(6),7,11-tetraen-5-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112212462D          

 25 29  0  0  1  0            999 V2000
    4.5283    2.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0803    1.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253    0.7634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6323    0.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1844    1.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9294    1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4814    2.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2884    2.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5434    1.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9913    1.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3684    1.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6233    2.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9559    2.9161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717    1.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -0.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3522   -0.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  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
  8 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 15 23  2  0  0  0  0
 19 23  1  0  0  0  0
 16 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv1652309112212462D          

 25 29  0  0  1  0            999 V2000
    4.5283    2.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0803    1.5480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253    0.7634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6323    0.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1844    1.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9294    1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4814    2.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2884    2.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5434    1.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9913    1.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3684    1.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6233    2.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9559    2.9161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717    1.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821   -0.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -0.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3522   -0.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  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
  8 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 15 23  2  0  0  0  0
 19 23  1  0  0  0  0
 16 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0313324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]1(CC2=CC=C3OCOC3=C2)OC2=C3C=COC3=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O6/c1-21-19(9-11-2-4-15-16(8-11)24-10-23-15)18(20)13-3-5-14-12(6-7-22-14)17(13)25-19/h2-8H,9-10H2,1H3/t19-/m1/s1

> <INCHI_KEY>
HNGNYODKSMNHQW-LJQANCHMSA-N

> <FORMULA>
C19H14O6

> <MOLECULAR_WEIGHT>
338.315

> <EXACT_MASS>
338.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.69884004144576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-4-methoxy-3,10-dioxatricyclo[7.3.0.0^{2,6}]dodeca-1,6,8,11-tetraen-5-one

> <JCHEM_LOGP>
3.458928783666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8604094643009574

> <JCHEM_POLAR_SURFACE_AREA>
67.13

> <JCHEM_REFRACTIVITY>
86.4898

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-(2H-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0^{2,6}]dodeca-1,6,8,11-tetraen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       8.453   4.034   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.483   2.890   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.007   1.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.514   1.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.544   2.249   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.068   3.714   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.099   4.858   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.605   4.538   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.081   3.074   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.050   1.929   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.621   3.074   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      16.097   4.538   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.851   5.443   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.600   2.051   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.570   0.907   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.340  -0.427   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.570  -1.760   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.030  -1.760   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.260  -0.427   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.754  -0.107   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.593   1.425   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.000   2.051   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.030   0.907   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.846  -0.107   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.991  -1.137   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14   24                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    3   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   19                                                  
CONECT   24   16    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄O₆

Average Mass

338.3150 Da

Monoisotopic Mass

338.07904 Da

IUPAC Name

(4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-4-methoxy-3,10-dioxatricyclo[7.3.0.0^{2,6}]dodeca-1,6,8,11-tetraen-5-one

Traditional Name

(4R)-4-(2H-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0^{2,6}]dodeca-1,6,8,11-tetraen-5-one

CAS Registry Number

Not Available

SMILES

CO[C@]1(CC2=CC=C3OCOC3=C2)OC2=C3C=COC3=CC=C2C1=O

InChI Identifier

InChI=1S/C19H14O6/c1-21-19(9-11-2-4-15-16(8-11)24-10-23-15)18(20)13-3-5-14-12(6-7-22-14)17(13)25-19/h2-8H,9-10H2,1H3/t19-/m1/s1

InChI Key

HNGNYODKSMNHQW-LJQANCHMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lonchocarpus castilloi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Benzodioxole
Benzofuran
Coumaran
Aryl ketone
Aryl alkyl ketone
Ketal
Benzenoid
Furan
Heteroaromatic compound
Ketone
Oxacycle
Organoheterocyclic compound
Acetal
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	3.46	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	67.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.49 m³·mol⁻¹	ChemAxon
Polarizability	33.7 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

163014447

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one (NP0313324)

MOL for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D MOL for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D SDF for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D-SDF for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

PDB for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D PDB for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

SMILES for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

INCHI for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

Structure for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D Structure for NP0313324 ((4r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-4-methoxy-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)