NP-MRD: Showing NP-Card for 10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one (NP0155077)

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Record Information

Version

2.0

Created at

2022-09-02 12:04:55 UTC

Updated at

2022-09-02 12:04:55 UTC

NP-MRD ID

NP0155077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one

Description

CHEMBL3596582 belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. 10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one is found in Mallotus philippensis. CHEMBL3596582 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514182D          

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 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
 11 37  2  0  0  0  0
  4 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(O)C(C)=C(O)C(CC2=C3OC(CC(=O)C3=C(O)C3=C2OC(C)(C)C=C3)C2=CC=CC=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O8/c1-14-24(33)18(27(36)22(15(2)31)25(14)34)12-19-28-17(10-11-30(3,4)38-28)26(35)23-20(32)13-21(37-29(19)23)16-8-6-5-7-9-16/h5-11,21,33-36H,12-13H2,1-4H3

> <INCHI_KEY>
AKTBFFHJRRKAMX-UHFFFAOYSA-N

> <FORMULA>
C30H28O8

> <MOLECULAR_WEIGHT>
516.546

> <EXACT_MASS>
516.178417862

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
54.198444968897206

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-9-hydroxy-13,13-dimethyl-5-phenyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-7-one

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
6.895029065666667

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.058019367493577

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.605985510260912

> <JCHEM_PKA_STRONGEST_BASIC>
-4.642506169050364

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
142.84529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.13e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-9-hydroxy-13,13-dimethyl-5-phenyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   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  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.428   2.604   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   37                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   37                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   30                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29   13   23                                                  
CONECT   31   16   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   11    4   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₈O₈

Average Mass

516.5460 Da

Monoisotopic Mass

516.17842 Da

IUPAC Name

2-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-9-hydroxy-13,13-dimethyl-5-phenyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-7-one

Traditional Name

2-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-9-hydroxy-13,13-dimethyl-5-phenyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1(10),2,8,11-tetraen-7-one

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)C(C)=C(O)C(CC2=C3OC(CC(=O)C3=C(O)C3=C2OC(C)(C)C=C3)C2=CC=CC=C2)=C1O

InChI Identifier

InChI=1S/C30H28O8/c1-14-24(33)18(27(36)22(15(2)31)25(14)34)12-19-28-17(10-11-30(3,4)38-28)26(35)23-20(32)13-21(37-29(19)23)16-8-6-5-7-9-16/h5-11,21,33-36H,12-13H2,1-4H3

InChI Key

AKTBFFHJRRKAMX-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
Mallotus philippensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
Linear 1,7-diphenylheptane skeleton
5-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Flavan
Pyranochromene
Alkyl-phenylketone
2,2-dimethyl-1-benzopyran
Acylphloroglucinol derivative
Chromone
Chromane
1-benzopyran
Benzopyran
Benzenetriol
Phloroglucinol derivative
Phenylketone
Acetophenone
Benzoyl
Aryl alkyl ketone
Aryl ketone
O-cresol
P-cresol
Toluene
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Ether
Polyol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Aldehyde
Organooxygen compound
Organic oxygen 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	4.54	ALOGPS
logP	6.9	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.85 m³·mol⁻¹	ChemAxon
Polarizability	54.2 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	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

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

12304392

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one (NP0155077)

MOL for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

3D MOL for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

3D SDF for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

3D-SDF for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

PDB for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

3D PDB for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

SMILES for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

INCHI for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

Structure for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)

3D Structure for NP0155077 (10-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5-hydroxy-8,8-dimethyl-2-phenyl-2h,3h-pyrano[3,2-g]chromen-4-one)