NP-MRD: Showing NP-Card for (4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one (NP0301872)

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Record Information

Version

2.0

Created at

2022-09-10 15:05:12 UTC

Updated at

2022-09-10 15:05:12 UTC

NP-MRD ID

NP0301872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one

Description

(4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one is found in Hypericum brasiliense.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102217052D          

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 33 39  2  0  0  0  0
  6 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309102217052D          

 40 41  0  0  1  0            999 V2000
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    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
    1.6585   -3.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  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
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  2  0  0  0  0
  9 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 33 39  2  0  0  0  0
  6 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301872

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC2=C(O)[C@@](CC=C(C)C)(C(=O)C(C)C)C(O)=C(C)C2=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O8/c1-15(2)10-11-20-26(35)21(28(37)23(27(20)36)24(33)17(5)6)14-22-25(34)19(9)30(39)32(31(22)40,13-12-16(3)4)29(38)18(7)8/h10,12,17-18,35-37,39-40H,11,13-14H2,1-9H3/t32-/m0/s1

> <INCHI_KEY>
GMXLMLBRZDSTNV-YTTGMZPUSA-N

> <FORMULA>
C32H42O8

> <MOLECULAR_WEIGHT>
554.68

> <EXACT_MASS>
554.287968312

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.914515339051555

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one

> <JCHEM_LOGP>
7.997713814000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.381032654954768

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0312590903077687

> <JCHEM_PKA_STRONGEST_BASIC>
-4.664043357309395

> <JCHEM_POLAR_SURFACE_AREA>
152.36

> <JCHEM_REFRACTIVITY>
160.11350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one

> <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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.519  -8.973   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.045  -7.525   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.562  -7.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.089  -5.811   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.552  -8.438   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.529 -10.687   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.539 -11.867   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.045 -10.955   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.035  -9.775   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.572 -12.402   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.096  -6.636   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   39                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20   25                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   14   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   11   30                                                  
CONECT   30   29                                                            
CONECT   31    9   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   39                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   33    6   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₂O₈

Average Mass

554.6800 Da

Monoisotopic Mass

554.28797 Da

IUPAC Name

(4S)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one

Traditional Name

(4S)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC2=C(O)[C@@](CC=C(C)C)(C(=O)C(C)C)C(O)=C(C)C2=O)=C1O

InChI Identifier

InChI=1S/C32H42O8/c1-15(2)10-11-20-26(35)21(28(37)23(27(20)36)24(33)17(5)6)14-22-25(34)19(9)30(39)32(31(22)40,13-12-16(3)4)29(38)18(7)8/h10,12,17-18,35-37,39-40H,11,13-14H2,1-9H3/t32-/m0/s1

InChI Key

GMXLMLBRZDSTNV-YTTGMZPUSA-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
Hypericum brasiliense	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	ChemAxon
pKa (Strongest Acidic)	3.03	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	160.11 m³·mol⁻¹	ChemAxon
Polarizability	59.91 Å³	ChemAxon
Number of Rings	2	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one (NP0301872)

MOL for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

3D MOL for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

3D SDF for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

3D-SDF for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

PDB for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

3D PDB for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

SMILES for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

INCHI for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

Structure for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)

3D Structure for NP0301872 ((4s)-3,5-dihydroxy-2-methyl-4-(3-methylbut-2-en-1-yl)-4-(2-methylpropanoyl)-6-{[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)phenyl]methyl}cyclohexa-2,5-dien-1-one)