NP-MRD: Showing NP-Card for Hyperwilsol D (NP0351155)

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Record Information

Version

2.0

Created at

2025-06-19 21:07:35 UTC

Updated at

2025-06-21 00:02:30 UTC

NP-MRD ID

NP0351155

Natural Product DOI

https://doi.org/10.57994/4144

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hyperwilsol D

Description

Hyperwilsol D was first documented in 2025 (PMID: 40436302). Based on a literature review very few articles have been published on Hyperwilsol D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01112321542D          

 33 33  0  0  1  0            999 V2000
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    3.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663   -1.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054   -2.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107   -3.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  2  0  0  0  0
  2  9  1  1  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
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 22 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END


  Mrv2104 01112321542D          

 33 33  0  0  1  0            999 V2000
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    3.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663   -1.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -0.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929   -2.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054   -2.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107   -3.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  2  0  0  0  0
  2  9  1  1  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
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 22 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(CC=C(C)C)C[C@H](CC=C(C)C)[C@@](C)(CCC=C(C)C)[C@@H](C(=O)C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O4/c1-19(2)12-11-16-28(9)23(14-13-20(3)4)18-29(27(32)33-10,17-15-21(5)6)26(31)24(28)25(30)22(7)8/h12-13,15,22-24H,11,14,16-18H2,1-10H3/t23-,24-,28+,29-/m0/s1

> <INCHI_KEY>
QVUJYADKXQKJHK-SBXDIWKWSA-N

> <FORMULA>
C29H46O4

> <MOLECULAR_WEIGHT>
458.683

> <EXACT_MASS>
458.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.17862080208681

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,3S,4R,5S)-4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

> <JCHEM_LOGP>
8.196698833000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.344552761667922

> <JCHEM_PKA_STRONGEST_BASIC>
-6.996007611337291

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
138.63150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,3S,4R,5S)-4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-JAN-23         0                                  
HETATM    1  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.173   3.222   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.163   4.402   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.636   5.849   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.626   7.029   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.119   6.117   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.344  -1.950   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.870  -3.397   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.119  -4.577   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.173  -1.682   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.324  -1.950   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.797  -3.397   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.787  -4.577   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.303  -4.309   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.260  -6.024   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9   15                                             
CONECT    3    2    4   32                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    2   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    2   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   15   22                                                       
CONECT   22   21   23   27   32                                             
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   22   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   22    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆O₄

Average Mass

458.6830 Da

Monoisotopic Mass

458.33961 Da

IUPAC Name

methyl (1S,3S,4R,5S)-4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

Traditional Name

methyl (1S,3S,4R,5S)-4-methyl-1,5-bis(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-en-1-yl)-3-(2-methylpropanoyl)-2-oxocyclohexane-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(CC=C(C)C)C[C@H](CC=C(C)C)[C@@](C)(CCC=C(C)C)[C@@H](C(=O)C(C)C)C1=O

InChI Identifier

InChI=1S/C29H46O4/c1-19(2)12-11-16-28(9)23(14-13-20(3)4)18-29(27(32)33-10,17-15-21(5)6)26(31)24(28)25(30)22(7)8/h12-13,15,22-24H,11,14,16-18H2,1-10H3/t23-,24-,28+,29-/m0/s1

InChI Key

QVUJYADKXQKJHK-SBXDIWKWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.0 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100.0, CDCl₃, simulated)	xty@nwsuaf.edu.cn	Northwest Agriculture and Forestry University	Xi-Tao Yan	2025-06-19	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Hypericum wilsonii		Not Available

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	8.2	ChemAxon
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	138.63 m³·mol⁻¹	ChemAxon
Polarizability	55.18 Å³	ChemAxon
Number of Rings	1	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang ZX, Chen NN, Zhao QQ, Wei H, Liu L, Yan XT: Hyperwilsol A, a highly modified 2-nor-polycyclic polyprenylated acylphloroglucinol possessing an unusual 6/6/5/5 spirotetracyclic skeleton from Hypericum wilsonii. Phytochemistry. 2025 May 26;238:114561. doi: 10.1016/j.phytochem.2025.114561. [PubMed:40436302 ]
DOI: 10.1016/j.phytochem.2025.114561

Showing NP-Card for Hyperwilsol D (NP0351155)

MOL for NP0351155 (Hyperwilsol D)

3D MOL for NP0351155 (Hyperwilsol D)

3D SDF for NP0351155 (Hyperwilsol D)

3D-SDF for NP0351155 (Hyperwilsol D)

PDB for NP0351155 (Hyperwilsol D)

3D PDB for NP0351155 (Hyperwilsol D)

SMILES for NP0351155 (Hyperwilsol D)

INCHI for NP0351155 (Hyperwilsol D)

Structure for NP0351155 (Hyperwilsol D)

3D Structure for NP0351155 (Hyperwilsol D)