NP-MRD: Showing NP-Card for 4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate (NP0300157)

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Record Information

Version

2.0

Created at

2022-09-10 12:24:15 UTC

Updated at

2022-09-10 12:24:15 UTC

NP-MRD ID

NP0300157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

Description

4-[5,7-Dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenyl-2H-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-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate is found in Kielmeyera reticulata. Based on a literature review very few articles have been published on 4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenyl-2H-chromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102214242D          

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M  END

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M  END


  Mrv1652309102214242D          

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   -1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 30 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
  6 41  2  0  0  0  0
 29 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(COC(=O)C=CC1=CC=CC=C1)CC(=O)C1=C(O)C(CC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H32O7/c1-21(2)14-16-25-32(38)31(27(35)18-22(3)20-40-28(36)17-15-23-10-6-4-7-11-23)33(39)30-26(19-29(37)41-34(25)30)24-12-8-5-9-13-24/h4-15,17,19,22,38-39H,16,18,20H2,1-3H3

> <INCHI_KEY>
RYOCGBKLTMGWME-UHFFFAOYSA-N

> <FORMULA>
C34H32O7

> <MOLECULAR_WEIGHT>
552.623

> <EXACT_MASS>
552.21480337

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
59.87553821591251

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenyl-2H-chromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

> <JCHEM_LOGP>
8.302931507333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.136895564302092

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.964398632299998

> <JCHEM_PKA_STRONGEST_BASIC>
-6.204020441199483

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
168.90459999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -6.160   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004  -6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.670  -8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   41                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   27                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27    9   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   41                                                  
CONECT   30   29   31   37                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   30   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40    6   29                                                  
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
4-[5,7-Dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenyl-2H-chromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₃₄H₃₂O₇

Average Mass

552.6230 Da

Monoisotopic Mass

552.21480 Da

IUPAC Name

4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenyl-2H-chromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

Traditional Name

4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-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)C(CC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

InChI Identifier

InChI=1S/C34H32O7/c1-21(2)14-16-25-32(38)31(27(35)18-22(3)20-40-28(36)17-15-23-10-6-4-7-11-23)33(39)30-26(19-29(37)41-34(25)30)24-12-8-5-9-13-24/h4-15,17,19,22,38-39H,16,18,20H2,1-3H3

InChI Key

RYOCGBKLTMGWME-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
4-phenylcoumarin
7-hydroxycoumarin
Cinnamic acid or derivatives
Hydroxycoumarin
Cinnamic acid ester
Butyrophenone
Coumarin
Benzopyran
1-benzopyran
Styrene
Aryl alkyl ketone
Aryl ketone
Fatty acid ester
Pyranone
Fatty acyl
Benzenoid
Pyran
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Heteroaromatic compound
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	8.3	ChemAxon
pKa (Strongest Acidic)	6.96	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	168.9 m³·mol⁻¹	ChemAxon
Polarizability	59.88 Å³	ChemAxon
Number of Rings	4	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

73107515

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate (NP0300157)

MOL for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D MOL for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D SDF for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D-SDF for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

PDB for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D PDB for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

SMILES for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

INCHI for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

Structure for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)

3D Structure for NP0300157 (4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate)