NP-MRD: Showing NP-Card for 5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one (NP0212008)

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Record Information

Version

2.0

Created at

2022-09-05 10:31:55 UTC

Updated at

2022-09-05 10:31:55 UTC

NP-MRD ID

NP0212008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one

Description

MESUAGENIN B 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. 5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one was first documented in 2010 (PMID: 20943395). Based on a literature review very few articles have been published on MESUAGENIN B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052212312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052212312D          

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M  END
> <DATABASE_ID>
NP0212008

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O5/c1-6-19(4)26(32)25-27(33)21-14-16-30(5,15-10-11-18(2)3)35-28(21)24-22(17-23(31)34-29(24)25)20-12-8-7-9-13-20/h7-9,11-14,16-17,19,33H,6,10,15H2,1-5H3

> <INCHI_KEY>
GEYVIFNRNUBPHZ-UHFFFAOYSA-N

> <FORMULA>
C30H32O5

> <MOLECULAR_WEIGHT>
472.581

> <EXACT_MASS>
472.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.28660465797109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenyl-2H,8H-pyrano[2,3-h]chromen-8-one

> <JCHEM_LOGP>
7.447022587333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.64917214546725

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.435810688443078

> <JCHEM_PKA_STRONGEST_BASIC>
-4.954597865867878

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
149.40640000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.746   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.874   6.105   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -3.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.564   2.104   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.438  -2.607   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.885  -3.134   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.153  -4.650   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.600  -5.177   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.973  -5.640   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   35                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   13   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23    7   12                                                  
CONECT   25   11   26                                                       
CONECT   26   25   27   28   34                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   26   35                                                       
CONECT   35   34   10                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₂O₅

Average Mass

472.5810 Da

Monoisotopic Mass

472.22497 Da

IUPAC Name

5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenyl-2H,8H-pyrano[2,3-h]chromen-8-one

Traditional Name

5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H32O5/c1-6-19(4)26(32)25-27(33)21-14-16-30(5,15-10-11-18(2)3)35-28(21)24-22(17-23(31)34-29(24)25)20-12-8-7-9-13-20/h7-9,11-14,16-17,19,33H,6,10,15H2,1-5H3

InChI Key

GEYVIFNRNUBPHZ-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

Not Available

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
Butyrophenone
Coumarin
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Lactone
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
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	7.45	ChemAxon
pKa (Strongest Acidic)	7.44	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	149.41 m³·mol⁻¹	ChemAxon
Polarizability	52.29 Å³	ChemAxon
Number of Rings	4	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

10363506

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13917758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Awang K, Chan G, Litaudon M, Ismail NH, Martin MT, Gueritte F: 4-Phenylcoumarins from Mesua elegans with acetylcholinesterase inhibitory activity. Bioorg Med Chem. 2010 Nov 15;18(22):7873-7. doi: 10.1016/j.bmc.2010.09.044. Epub 2010 Sep 25. [PubMed:20943395 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one (NP0212008)

MOL for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

3D MOL for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

3D SDF for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

3D-SDF for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

PDB for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

3D PDB for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

SMILES for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

INCHI for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

Structure for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)

3D Structure for NP0212008 (5-hydroxy-2-methyl-6-(2-methylbutanoyl)-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one)