NP-MRD: Showing NP-Card for (2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one (NP0320224)

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Record Information

Version

2.0

Created at

2022-09-11 21:45:28 UTC

Updated at

2022-09-11 21:45:28 UTC

NP-MRD ID

NP0320224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one

Description

(2S)-2-(2,4-Dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2,3-dihydropyrano[2,3-g]chromen-4(7H)-one belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. Based on a literature review very few articles have been published on (2S)-2-(2,4-Dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2,3-dihydropyrano[2,3-g]chromen-4(7H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223452D          

 34 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309112223452D          

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M  END
> <DATABASE_ID>
NP0320224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C([C@@H]2CC(=O)C3=C(O2)C(CC=C(C)C)=C2C=CC(C)(C)OC2=C3OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O6/c1-16(2)8-10-18-19-12-13-28(3,4)34-26(19)27(32-7)24-21(29)15-23(33-25(18)24)20-11-9-17(30-5)14-22(20)31-6/h8-9,11-14,23H,10,15H2,1-7H3/t23-/m0/s1

> <INCHI_KEY>
FZMRUMHVVNEBRJ-QHCPKHFHSA-N

> <FORMULA>
C28H32O6

> <MOLECULAR_WEIGHT>
464.558

> <EXACT_MASS>
464.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.86628060163311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-(2,4-dimethoxyphenyl)-9-methoxy-12,12-dimethyl-2-(3-methylbut-2-en-1-yl)-4,11-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,13-tetraen-7-one

> <JCHEM_LOGP>
5.251980619666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.601623719629444

> <JCHEM_PKA_STRONGEST_BASIC>
-4.208309591801546

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
133.3729

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-(2,4-dimethoxyphenyl)-9-methoxy-12,12-dimethyl-2-(3-methylbut-2-en-1-yl)-4,11-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,13-tetraen-7-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      13.337   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.527  -1.447   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.517   0.267   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   29                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   11   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   19                                                       
CONECT   30   12    7                                                       
CONECT   31    6   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31    3                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₆

Average Mass

464.5580 Da

Monoisotopic Mass

464.21989 Da

IUPAC Name

(5S)-5-(2,4-dimethoxyphenyl)-9-methoxy-12,12-dimethyl-2-(3-methylbut-2-en-1-yl)-4,11-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,13-tetraen-7-one

Traditional Name

(5S)-5-(2,4-dimethoxyphenyl)-9-methoxy-12,12-dimethyl-2-(3-methylbut-2-en-1-yl)-4,11-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,13-tetraen-7-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C([C@@H]2CC(=O)C3=C(O2)C(CC=C(C)C)=C2C=CC(C)(C)OC2=C3OC)C(OC)=C1

InChI Identifier

InChI=1S/C28H32O6/c1-16(2)8-10-18-19-12-13-28(3,4)34-26(19)27(32-7)24-21(29)15-23(33-25(18)24)20-11-9-17(30-5)14-22(20)31-6/h8-9,11-14,23H,10,15H2,1-7H3/t23-/m0/s1

InChI Key

FZMRUMHVVNEBRJ-QHCPKHFHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

8-prenylated flavanone
2p-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
Flavanone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
M-dimethoxybenzene
Dimethoxybenzene
Methoxybenzene
Phenol ether
Aryl alkyl ketone
Aryl ketone
Phenoxy compound
Anisole
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	5.25	ChemAxon
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.37 m³·mol⁻¹	ChemAxon
Polarizability	51.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

8565158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10389716

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one (NP0320224)

MOL for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

3D MOL for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

3D SDF for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

3D-SDF for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

PDB for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

3D PDB for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

SMILES for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

INCHI for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

Structure for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)

3D Structure for NP0320224 ((2s)-2-(2,4-dimethoxyphenyl)-5-methoxy-7,7-dimethyl-10-(3-methylbut-2-en-1-yl)-2h,3h-pyrano[2,3-g]chromen-4-one)