NP-MRD: Showing NP-Card for (2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one (NP0313293)

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Record Information

Version

2.0

Created at

2022-09-11 10:44:09 UTC

Updated at

2022-09-11 10:44:09 UTC

NP-MRD ID

NP0313293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one

Description

CHEMBL3235992 belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. (2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one is found in Toddalia asiatica. Based on a literature review very few articles have been published on CHEMBL3235992.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112212442D          

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 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  2  0  0  0  0
 26 37  1  0  0  0  0
 18 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C=CC(=O)OC2=C1\C=C\[C@H]1C[C@@H](C=C(C)C)C2=C(O1)C1=CC=CC=C1N(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H29NO6/c1-17(2)14-18-15-19(36-29-20-8-6-7-9-23(20)31(3)30(33)27(18)29)10-11-21-24(34-4)16-25(35-5)22-12-13-26(32)37-28(21)22/h6-14,16,18-19H,15H2,1-5H3/b11-10+/t18-,19+/m1/s1

> <INCHI_KEY>
MBVIZLALYQOVGW-ONNQBUSKSA-N

> <FORMULA>
C30H29NO6

> <MOLECULAR_WEIGHT>
499.563

> <EXACT_MASS>
499.199487658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
53.47004866011338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4S)-2-[(E)-2-(5,7-dimethoxy-2-oxo-2H-chromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2H,3H,4H,5H,6H-pyrano[3,2-c]quinolin-5-one

> <JCHEM_LOGP>
4.133598342000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.41793668474042234

> <JCHEM_POLAR_SURFACE_AREA>
74.30000000000001

> <JCHEM_REFRACTIVITY>
144.4327

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4S)-2-[(E)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2H,3H,4H-pyrano[3,2-c]quinolin-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       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.804  -3.231   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.034  -4.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804  -5.898   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034  -7.232   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.804  -8.566   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.034  -9.899   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494  -7.232   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -8.566   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -8.566   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -7.232   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.874  -7.232   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.184  -5.898   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.724  -5.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       2.874   3.437   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   37                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   35                                                  
CONECT   26   25   27   37                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   25   36                                                  
CONECT   36   35                                                            
CONECT   37   26   18                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₉NO₆

Average Mass

499.5630 Da

Monoisotopic Mass

499.19949 Da

IUPAC Name

(2R,4S)-2-[(E)-2-(5,7-dimethoxy-2-oxo-2H-chromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2H,3H,4H,5H,6H-pyrano[3,2-c]quinolin-5-one

Traditional Name

(2R,4S)-2-[(E)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2H,3H,4H-pyrano[3,2-c]quinolin-5-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C=CC(=O)OC2=C1\C=C\[C@H]1C[C@@H](C=C(C)C)C2=C(O1)C1=CC=CC=C1N(C)C2=O

InChI Identifier

InChI=1S/C30H29NO6/c1-17(2)14-18-15-19(36-29-20-8-6-7-9-23(20)31(3)30(33)27(18)29)10-11-21-24(34-4)16-25(35-5)22-12-13-26(32)37-28(21)22/h6-14,16,18-19H,15H2,1-5H3/b11-10+/t18-,19+/m1/s1

InChI Key

MBVIZLALYQOVGW-ONNQBUSKSA-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

Species Name	Source	Reference
Toddalia asiatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Pyranoquinolines

Alternative Parents

Substituents

Pyranoquinoline
Coumarin
Dihydroquinolone
Benzopyran
Dihydroquinoline
Pyranopyridine
1-benzopyran
Anisole
Phenol ether
Styrene
Pyridinone
Pyranone
Alkyl aryl ether
Pyridine
Pyran
Benzenoid
Vinylogous ester
Heteroaromatic compound
Lactone
Lactam
Oxacycle
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	4.13	ChemAxon
pKa (Strongest Basic)	-0.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	144.43 m³·mol⁻¹	ChemAxon
Polarizability	53.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

34238967

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90655368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one (NP0313293)

MOL for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

3D MOL for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

3D SDF for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

3D-SDF for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

PDB for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

3D PDB for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

SMILES for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

INCHI for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

Structure for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)

3D Structure for NP0313293 ((2r,4s)-2-[(1e)-2-(5,7-dimethoxy-2-oxochromen-8-yl)ethenyl]-6-methyl-4-(2-methylprop-1-en-1-yl)-2h,3h,4h-pyrano[3,2-c]quinolin-5-one)