NP-MRD: Showing NP-Card for 4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate (NP0329139)

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Record Information

Version

2.0

Created at

2022-09-12 13:14:46 UTC

Updated at

2022-09-12 13:14:46 UTC

NP-MRD ID

NP0329139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

Description

4-{5-Hydroxy-2,2-dimethyl-8-oxo-10-phenyl-2H,8H-pyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. 4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate is found in Kielmeyera reticulata. 4-{5-Hydroxy-2,2-dimethyl-8-oxo-10-phenyl-2H,8H-pyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231523512D          

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  Mrv1533004231523512D          

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   12.1460    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.0000    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 18 35  1  0  0  0  0
 29 35  2  0  0  0  0
 30 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(COC(=O)C=CC1=CC=CC=C1)CC(=O)C1=C(O)C2=C(OC(C)(C)C=C2)C2=C1OC(=O)C=C2C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H30O7/c1-21(20-39-27(36)15-14-22-10-6-4-7-11-22)18-26(35)30-31(38)24-16-17-34(2,3)41-32(24)29-25(19-28(37)40-33(29)30)23-12-8-5-9-13-23/h4-17,19,21,38H,18,20H2,1-3H3

> <INCHI_KEY>
DFLKNPBHNWMIQQ-UHFFFAOYSA-N

> <FORMULA>
C34H30O7

> <MOLECULAR_WEIGHT>
550.607

> <EXACT_MASS>
550.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
59.37902042132009

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenyl-2H,8H-pyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
5.94

> <JCHEM_LOGP>
7.128553231666667

> <ALOGPS_LOGS>
-6.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.829342214756768

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.446784640816832

> <JCHEM_PKA_STRONGEST_BASIC>
-4.946929467450076

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
167.07429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.91e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -3.850   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       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004  -1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      17.338   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.004   3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.672   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.005   5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.339   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.866   6.067   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.855   4.353   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.339   3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.005   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.339   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.005  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      20.005  -3.850   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      18.672  -1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      18.672   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.673   0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      24.006   3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      25.340   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      25.340   0.770   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      24.006   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    2   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   35                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   21   29                                                  
CONECT   29   28   30   35                                                  
CONECT   30   29   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   18   29                                                  
CONECT   36   30   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenyl-2H,8H-pyrano[2,3-H]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₃₄H₃₀O₇

Average Mass

550.6070 Da

Monoisotopic Mass

550.19915 Da

IUPAC Name

4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenyl-2H,8H-pyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

Traditional Name

4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(COC(=O)C=CC1=CC=CC=C1)CC(=O)C1=C(O)C2=C(OC(C)(C)C=C2)C2=C1OC(=O)C=C2C1=CC=CC=C1

InChI Identifier

InChI=1S/C34H30O7/c1-21(20-39-27(36)15-14-22-10-6-4-7-11-22)18-26(35)30-31(38)24-16-17-34(2,3)41-32(24)29-25(19-28(37)40-33(29)30)23-12-8-5-9-13-23/h4-17,19,21,38H,18,20H2,1-3H3

InChI Key

DFLKNPBHNWMIQQ-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
Kielmeyera reticulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
Pyranoneoflavonoid
4-phenylcoumarin
Pyranocoumarin
Angular pyranocoumarin
Cinnamic acid or derivatives
Cinnamic acid ester
2,2-dimethyl-1-benzopyran
Butyrophenone
Coumarin
Benzopyran
1-benzopyran
Styrene
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Fatty acid ester
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Pyran
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Heteroaromatic compound
Carboxylic acid ester
Ketone
Lactone
Ether
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
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	5.94	ALOGPS
logP	7.13	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	7.45	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	167.07 m³·mol⁻¹	ChemAxon
Polarizability	59.38 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

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-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate (NP0329139)

MOL for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D MOL for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D SDF for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D-SDF for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

PDB for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D PDB for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

SMILES for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

INCHI for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

Structure for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D Structure for NP0329139 (4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)