NP-MRD: Showing NP-Card for maackiapentone (NP0038085)

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Record Information

Version

2.0

Created at

2021-06-20 20:52:13 UTC

Updated at

2021-06-30 00:10:40 UTC

NP-MRD ID

NP0038085

Secondary Accession Numbers

None

Natural Product Identification

Common Name

maackiapentone

Provided By

JEOL Database JEOL Logo

Description

5-Hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. maackiapentone is found in Maackia amurensis. maackiapentone was first documented in 2009 (Li, X., et al.). Based on a literature review very few articles have been published on 5-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122523D          

 67 70  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122523D          

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M  END
> <DATABASE_ID>
NP0038085

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C1=C([H])OC2=C3C([H])=C([H])C(OC3=C(C(O[H])=C2C1=O)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

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

> <INCHI_KEY>
FROPDIHHPYQQQP-UHFFFAOYSA-N

> <FORMULA>
C30H32O5

> <MOLECULAR_WEIGHT>
472.581

> <EXACT_MASS>
472.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.898276829184205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.50

> <JCHEM_LOGP>
7.738195112

> <ALOGPS_LOGS>
-5.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.785162546982901

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.362165798106186

> <JCHEM_PKA_STRONGEST_BASIC>
-4.805489721241546

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
142.581

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.25e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)pyrano[2,3-h]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 33 66  1  0
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  5 44  1  0
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 28 59  1  0
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 29 61  1  0
 29 62  1  0
 35 67  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -9.096   3.752   1.326  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.893   4.178   0.530  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.121   5.406  -0.316  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.690   3.570   0.535  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.268   2.341   1.298  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.673   1.280   0.398  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.282   1.061   0.425  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.676   0.066  -0.360  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.217  -0.141  -0.311  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.494  -0.203  -1.439  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.138  -0.380  -1.537  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.593  -0.512  -0.378  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.979  -0.708  -0.494  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.754  -0.847   0.669  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.167  -0.769   1.948  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.012  -0.917   3.199  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.143  -2.353   3.636  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.263  -3.091   3.769  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.659  -2.615   3.482  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.184  -4.519   4.244  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.778  -0.587   2.037  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.221  -0.543   3.293  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.006  -0.457   0.881  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.465  -0.259   0.965  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.007  -0.200   2.066  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.114  -1.020   0.627  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.721  -1.448  -0.607  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.937  -2.963  -0.526  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.079  -0.737  -0.666  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.927  -1.108  -1.843  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.640  -0.753  -1.797  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.490  -0.727  -1.180  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.868  -0.516  -1.228  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.449   0.485  -0.454  0.00  0.00           C+0
HETATM   35  O   UNK     0      -7.801   0.631  -0.581  0.00  0.00           O+0
HETATM   36  H   UNK     0      -8.911   2.890   1.970  0.00  0.00           H+0
HETATM   37  H   UNK     0      -9.917   3.489   0.651  0.00  0.00           H+0
HETATM   38  H   UNK     0      -9.429   4.572   1.971  0.00  0.00           H+0
HETATM   39  H   UNK     0      -7.231   5.693  -0.884  0.00  0.00           H+0
HETATM   40  H   UNK     0      -8.399   6.256   0.317  0.00  0.00           H+0
HETATM   41  H   UNK     0      -8.929   5.226  -1.033  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.895   3.999  -0.077  0.00  0.00           H+0
HETATM   43  H   UNK     0      -7.084   1.888   1.867  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.527   2.649   2.047  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.663   1.673   1.081  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.916  -0.107  -2.433  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.980  -0.431   3.046  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.561  -0.348   4.021  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.188  -2.814   3.888  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.149  -3.290   2.772  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.702  -1.613   3.051  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.248  -2.604   4.405  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.763  -4.645   5.165  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.589  -5.194   3.483  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.156  -4.833   4.452  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.751  -0.418   3.203  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.450  -3.351  -1.413  0.00  0.00           H+0
HETATM   58  H   UNK     0       5.531  -3.226   0.356  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.982  -3.493  -0.422  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.949   0.352  -0.689  0.00  0.00           H+0
HETATM   61  H   UNK     0       6.673  -0.958   0.228  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.660  -1.033  -1.547  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.425  -1.183  -2.806  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.083  -0.526  -2.698  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.064  -1.524  -1.786  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.492  -1.133  -1.869  0.00  0.00           H+0
HETATM   67  H   UNK     0      -8.054   1.497  -0.221  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   39   40   41                                             
CONECT    4    5    2   42                                                  
CONECT    5    6    4   43   44                                             
CONECT    6    7    5   34                                                  
CONECT    7    6    8   45                                                  
CONECT    8    7   32    9                                                  
CONECT    9   24   10    8                                                  
CONECT   10    9   11   46                                                  
CONECT   11   12   10                                                       
CONECT   12   13   23   11                                                  
CONECT   13   12   14   31                                                  
CONECT   14   26   13   15                                                  
CONECT   15   21   16   14                                                  
CONECT   16   17   15   47   48                                             
CONECT   17   18   16   49                                                  
CONECT   18   20   17   19                                                  
CONECT   19   18   50   51   52                                             
CONECT   20   18   53   54   55                                             
CONECT   21   15   22   23                                                  
CONECT   22   21   56                                                       
CONECT   23   12   24   21                                                  
CONECT   24   23    9   25                                                  
CONECT   25   24                                                            
CONECT   26   14   27                                                       
CONECT   27   26   30   28   29                                             
CONECT   28   27   57   58   59                                             
CONECT   29   27   60   61   62                                             
CONECT   30   31   27   63                                                  
CONECT   31   13   30   64                                                  
CONECT   32    8   33   65                                                  
CONECT   33   34   32   66                                                  
CONECT   34   33    6   35                                                  
CONECT   35   34   67                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    5                                                            
CONECT   44    5                                                            
CONECT   45    7                                                            
CONECT   46   10                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   22                                                            
CONECT   57   28                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   33                                                            
CONECT   67   35                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  140    0
END

RDKit          3D

67 70  0  0  0  0  0  0  0  0999 V2000
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 35 67  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₂O₅

Average Mass

472.5810 Da

Monoisotopic Mass

472.22497 Da

IUPAC Name

5-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-h]chromen-4-one

Traditional Name

5-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)pyrano[2,3-h]chromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C1=C([H])OC2=C3C([H])=C([H])C(OC3=C(C(O[H])=C2C1=O)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

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

InChI Key

FROPDIHHPYQQQP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Maackia amurensis	JEOL database	Li, X., et al, Chem. Pharm. Bull. 57, 302 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Pyranoisoflavonoid
Isoflavone
Hydroxyisoflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
Alkyl aryl ether
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	6.5	ALOGPS
logP	7.74	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.58 m³·mol⁻¹	ChemAxon
Polarizability	54.9 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	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

25231268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, X., et al. (2009). Li, X., et al, Chem. Pharm. Bull. 57, 302 (2009). Chem. Pharm. Bull..

Showing NP-Card for maackiapentone (NP0038085)

MOL for NP0038085 (maackiapentone)

3D MOL for NP0038085 (maackiapentone)

3D SDF for NP0038085 (maackiapentone)

3D-SDF for NP0038085 (maackiapentone)

PDB for NP0038085 (maackiapentone)

3D PDB for NP0038085 (maackiapentone)

SMILES for NP0038085 (maackiapentone)

INCHI for NP0038085 (maackiapentone)

Structure for NP0038085 (maackiapentone)

3D Structure for NP0038085 (maackiapentone)