NP-MRD: Showing NP-Card for Wikstrocin E (NP0044709)

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Record Information

Version

2.0

Created at

2022-02-24 21:13:03 UTC

Updated at

2022-02-24 21:13:03 UTC

NP-MRD ID

NP0044709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wikstrocin E

Description

Wikstrocin E was first documented in 2021 (PMID: 34445872).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302242222132D          

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M  END

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M  END


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    0.3954   -1.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -2.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4264   -1.6456    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 26 37  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@]3([H])[C@@H](OO)C(CO)=C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@H](C)C[C@@]1(OC(=O)CCCCCCC)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O8/c1-6-7-8-9-10-11-20(30)35-27-13-17(3)28(33)19-12-16(2)24(31)26(19,32)14-18(15-29)22(36-34)21(28)23(27)25(27,4)5/h12,14,17,19,21-23,29,32-34H,6-11,13,15H2,1-5H3/t17-,19-,21+,22+,23-,26-,27+,28+/m1/s1

> <INCHI_KEY>
HGNPIUHCHVPJFJ-WIGKQVRUSA-N

> <FORMULA>
C28H42O8

> <MOLECULAR_WEIGHT>
506.636

> <EXACT_MASS>
506.287968312

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.84950962975266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6R,9R,10R,11R,13S,15R)-9-hydroperoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,7-dien-13-yl octanoate

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
3.032957215333333

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.372396721441191

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.600410695061282

> <JCHEM_PKA_STRONGEST_BASIC>
-2.770412238453167

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
133.911

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,9R,10R,11R,13S,15R)-9-hydroperoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,7-dien-13-yl octanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-22         0                                  
HETATM    1  H   UNK     0       0.174  -1.102   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.508  -1.872   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.278  -0.539   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       2.946   0.849   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       1.318   0.665   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.183   0.323   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.637  -1.149   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.661   2.167   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.457   3.127   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.977   2.564   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.048   2.835   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.436   2.167   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.367   3.705   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.758   2.957   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.896   4.490   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.917   1.943   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.419   2.286   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.312   0.527   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.778   0.665   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       3.277   1.008   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       3.818  -0.539   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.354  -0.654   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.588  -1.872   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.128  -1.872   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.818  -3.206   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.278  -3.206   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.278  -4.746   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.612  -5.516   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.612  -7.056   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.946  -4.746   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.279  -5.516   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.613  -4.746   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.947  -5.516   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.280  -4.746   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.614  -5.516   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.948  -4.746   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.738  -3.206   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.087  -4.602   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.796  -3.072   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26   37                                             
CONECT    3    2    4    5   21                                             
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    3   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    2   27   37                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   26    2   38   39                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₈

Average Mass

506.6360 Da

Monoisotopic Mass

506.28797 Da

IUPAC Name

(1R,2S,6R,9R,10R,11R,13S,15R)-9-hydroperoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,7-dien-13-yl octanoate

Traditional Name

(1R,2S,6R,9R,10R,11R,13S,15R)-9-hydroperoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,7-dien-13-yl octanoate

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@]3([H])[C@@H](OO)C(CO)=C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@H](C)C[C@@]1(OC(=O)CCCCCCC)C2(C)C

InChI Identifier

InChI=1S/C28H42O8/c1-6-7-8-9-10-11-20(30)35-27-13-17(3)28(33)19-12-16(2)24(31)26(19,32)14-18(15-29)22(36-34)21(28)23(27)25(27,4)5/h12,14,17,19,21-23,29,32-34H,6-11,13,15H2,1-5H3/t17-,19-,21+,22+,23-,26-,27+,28+/m1/s1

InChI Key

HGNPIUHCHVPJFJ-WIGKQVRUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Wikstroemia lamatsoensis	Linington's dataset npmrd_submissions_20220207	34445872

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	3.08	ALOGPS
logP	3.03	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	133.91 m³·mol⁻¹	ChemAxon
Polarizability	56.85 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

Not Available

References

General References

Zhang M, Otsuki K, Kikuchi T, Bai ZS, Zhou D, Huang L, Chen CH, Morris-Natschke SL, Lee KH, Li N, Koike K, Li W: LC-MS Identification, Isolation, and Structural Elucidation of Anti-HIV Tigliane Diterpenoids from Wikstroemia lamatsoensis. J Nat Prod. 2021 Aug 27;84(8):2366-2373. doi: 10.1021/acs.jnatprod.1c00570. Epub 2021 Aug 17. [PubMed:34445872 ]

Showing NP-Card for Wikstrocin E (NP0044709)

MOL for NP0044709 (Wikstrocin E)

3D MOL for NP0044709 (Wikstrocin E)

3D SDF for NP0044709 (Wikstrocin E)

3D-SDF for NP0044709 (Wikstrocin E)

PDB for NP0044709 (Wikstrocin E)

3D PDB for NP0044709 (Wikstrocin E)

SMILES for NP0044709 (Wikstrocin E)

INCHI for NP0044709 (Wikstrocin E)

Structure for NP0044709 (Wikstrocin E)

3D Structure for NP0044709 (Wikstrocin E)