NP-MRD: Showing NP-Card for 4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one (NP0256631)

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Record Information

Version

2.0

Created at

2022-09-07 21:31:28 UTC

Updated at

2022-09-07 21:31:29 UTC

NP-MRD ID

NP0256631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one

Description

4,7,8-Trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]Dodeca-1,6,8,11-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). 4,7,8-Trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]Dodeca-1,6,8,11-tetraen-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241502302D          

 28 31  0  0  0  0            999 V2000
    8.5631    3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3082    2.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5012    2.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2463    1.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393    1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8873    1.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0803    1.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323    0.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8873   -0.1928    0.0000 C   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
    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
    3.5196   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196   -2.3720    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   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -2.3720    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
    6.1422    2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9492    2.6757    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
  8 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
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 12 26  2  0  0  0  0
 22 26  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  2  0  0  0  0
  3 28  1  0  0  0  0
M  END


  Mrv1533004241502302D          

 28 31  0  0  0  0            999 V2000
    8.5631    3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3082    2.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5012    2.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2463    1.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393    1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8873    1.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0803    1.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323    0.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8873   -0.1928    0.0000 C   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
    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
    3.5196   -0.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196   -2.3720    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   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -2.3720    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
    6.1422    2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9492    2.6757    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
  8 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
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 12 26  2  0  0  0  0
 22 26  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  2  0  0  0  0
  3 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256631

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC2(OC)OC3=C4C=COC4=C(OC)C(OC)=C3C2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O7/c1-23-13-7-5-12(6-8-13)11-21(26-4)20(22)15-16(28-21)14-9-10-27-17(14)19(25-3)18(15)24-2/h5-10H,11H2,1-4H3

> <INCHI_KEY>
UWLVCUXTZLXWJS-UHFFFAOYSA-N

> <FORMULA>
C21H20O7

> <MOLECULAR_WEIGHT>
384.384

> <EXACT_MASS>
384.120902984

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.944787625619384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
3.362681518999999

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8278981406766888

> <JCHEM_POLAR_SURFACE_AREA>
76.36000000000001

> <JCHEM_REFRACTIVITY>
100.11250000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      15.984   5.635   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.509   4.170   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.002   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.526   2.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.020   2.065   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.990   3.210   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.483   2.890   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.007   1.425   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.514   1.105   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.990  -0.360   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.600   2.051   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.570   0.907   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.340  -0.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.846  -0.107   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.991  -1.137   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.570  -1.760   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.340  -3.094   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.570  -4.428   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.030  -1.760   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.260  -3.094   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.030  -4.428   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.260  -0.427   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.754  -0.107   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.593   1.425   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.000   2.051   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.030   0.907   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.465   4.674   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.972   4.995   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11   14                                             
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   12   22                                                  
CONECT   27    6   28                                                       
CONECT   28   27    3                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₇

Average Mass

384.3840 Da

Monoisotopic Mass

384.12090 Da

IUPAC Name

4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one

Traditional Name

4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC2(OC)OC3=C4C=COC4=C(OC)C(OC)=C3C2=O)C=C1

InChI Identifier

InChI=1S/C21H20O7/c1-23-13-7-5-12(6-8-13)11-21(26-4)20(22)15-16(28-21)14-9-10-27-17(14)19(25-3)18(15)24-2/h5-10H,11H2,1-4H3

InChI Key

UWLVCUXTZLXWJS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Coumaran
Benzofuran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Ketal
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Ketone
Oxacycle
Ether
Acetal
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	3.08	ALOGPS
logP	3.36	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	76.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	100.11 m³·mol⁻¹	ChemAxon
Polarizability	37.94 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one (NP0256631)

MOL for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D MOL for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D SDF for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D-SDF for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

PDB for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D PDB for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

SMILES for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

INCHI for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

Structure for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)

3D Structure for NP0256631 (4,7,8-trimethoxy-4-[(4-methoxyphenyl)methyl]-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1,6,8,11-tetraen-5-one)