NP-MRD: Showing NP-Card for 4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate (NP0208050)

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Record Information

Version

2.0

Created at

2022-09-05 04:54:28 UTC

Updated at

2022-09-05 04:54:28 UTC

NP-MRD ID

NP0208050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate

Description

4-(7-Hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate 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. 4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate is found in Tephrosia purpurea. 4-(7-Hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512342D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251512342D          

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M  END
> <DATABASE_ID>
NP0208050

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OCC(C1OC(=O)C=CC1=CC=CC=C1)C1=C(O)C=CC2=C1OC(CC2=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O6/c1-30(2)29(36-26(33)16-13-19-9-5-3-6-10-19)22(18-34-30)27-23(31)15-14-21-24(32)17-25(35-28(21)27)20-11-7-4-8-12-20/h3-16,22,25,29,31H,17-18H2,1-2H3

> <INCHI_KEY>
QBEVDWJGVNNOGT-UHFFFAOYSA-N

> <FORMULA>
C30H28O6

> <MOLECULAR_WEIGHT>
484.548

> <EXACT_MASS>
484.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.86074861408691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(7-hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
5.545812109333333

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.97523915146489

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.569508186258286

> <JCHEM_PKA_STRONGEST_BASIC>
-4.116241064187479

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
136.27749999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       3.276  -8.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.437  -6.990   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.944  -7.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.897  -6.990   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.421  -5.525   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.913  -5.525   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.378  -5.049   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.522  -6.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.202  -7.586   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.987  -5.604   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.131  -6.634   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.811  -8.141   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.956  -9.171   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.635 -10.677   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.171 -11.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.026 -10.123   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.347  -8.617   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -3.080   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
HETATM   35  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    6   20   30                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   19   24                                                  
CONECT   31   28   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
4-(7-Hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₃₀H₂₈O₆

Average Mass

484.5480 Da

Monoisotopic Mass

484.18859 Da

IUPAC Name

4-(7-hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate

Traditional Name

4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC1(C)OCC(C1OC(=O)C=CC1=CC=CC=C1)C1=C(O)C=CC2=C1OC(CC2=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H28O6/c1-30(2)29(36-26(33)16-13-19-9-5-3-6-10-19)22(18-34-30)27-23(31)15-14-21-24(32)17-25(35-28(21)27)20-11-7-4-8-12-20/h3-16,22,25,29,31H,17-18H2,1-2H3

InChI Key

QBEVDWJGVNNOGT-UHFFFAOYSA-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
Tephrosia purpurea	LOTUS Database	35616633

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
7-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Cinnamic acid ester
Cinnamic acid or derivatives
Chromone
1-benzopyran
Chromane
Benzopyran
Styrene
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Oxolane
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Dialkyl ether
Carbonyl group
Organic oxygen compound
Organic oxide
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	5.4	ALOGPS
logP	5.55	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.28 m³·mol⁻¹	ChemAxon
Polarizability	50.86 Å³	ChemAxon
Number of Rings	5	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

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

85209866

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-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate (NP0208050)

MOL for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

3D MOL for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

3D SDF for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

3D-SDF for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

PDB for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

3D PDB for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

SMILES for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

INCHI for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

Structure for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)

3D Structure for NP0208050 (4-(7-hydroxy-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-8-yl)-2,2-dimethyloxolan-3-yl 3-phenylprop-2-enoate)