NP-MRD: Showing NP-Card for Crotokilwaepoxide D (NP0331517)

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Record Information

Version

2.0

Created at

2023-02-18 00:02:50 UTC

Updated at

2024-09-03 04:16:00 UTC

NP-MRD ID

NP0331517

Natural Product DOI

https://doi.org/10.57994/0487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Crotokilwaepoxide D

Description

Crotokilwaepoxide D belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on Crotokilwaepoxide D.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652302182301022D          

 32 38  0  0  1  0            999 V2000
    5.4111    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7152    0.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647   -0.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659   -0.2404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0466   -0.3377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981   -1.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -1.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -0.8631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7387   -1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -0.8989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226   -0.0438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8029   -0.3117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024    0.5430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3842    1.3386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1798    1.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860    1.5474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1659    2.1342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061    0.9605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8043    0.7518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244    0.1649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5352   -0.2885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4970   -1.1126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359   -1.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741   -2.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9304   -1.0464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    0.2268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9046    0.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1820    0.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    1.1715    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228    0.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477    1.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414    1.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 14 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 18 28  1  0  0  0  0
 13 29  1  1  0  0  0
 13 30  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  2  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END


  Mrv1652302182301022D          

 32 38  0  0  1  0            999 V2000
    5.4111    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7152    0.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647   -0.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659   -0.2404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0466   -0.3377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981   -1.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -1.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -0.8631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7387   -1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -0.8989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226   -0.0438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8029   -0.3117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024    0.5430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3842    1.3386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1798    1.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860    1.5474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1659    2.1342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061    0.9605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8043    0.7518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244    0.1649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5352   -0.2885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4970   -1.1126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359   -1.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741   -2.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9304   -1.0464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    0.2268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9046    0.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1820    0.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    1.1715    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228    0.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477    1.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414    1.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 14 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 18 28  1  0  0  0  0
 13 29  1  1  0  0  0
 13 30  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  2  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331517

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@]3(CO3)[C@]3([H])[C@@]([H])(C1=C(C)C(=O)O2)[C@]1(C)O[C@@H]1[C@@]12C[C@@H](C)[C@@H](OC(C)=O)[C@@]31O2

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O7/c1-9-7-21-18-19(4,28-18)14-13-10(2)17(24)27-12(13)5-6-20(8-25-20)15(14)22(21,29-21)16(9)26-11(3)23/h9,12,14-16,18H,5-8H2,1-4H3/t9-,12+,14-,15+,16-,18+,19+,20+,21+,22+/m1/s1

> <INCHI_KEY>
UORZKWLRBDPPDZ-HLXNSTBUSA-N

> <FORMULA>
C22H26O7

> <MOLECULAR_WEIGHT>
402.443

> <EXACT_MASS>
402.167853177

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.81812714763607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,5S,10S,13R,14S,15S,16R,17R)-4,7,17-trimethyl-8-oxo-3,9,19-trioxaspiro[hexacyclo[13.3.1.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,10}]nonadecane-13,2'-oxiran]-6-en-16-yl acetate

> <JCHEM_LOGP>
1.1672544043333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.067130757305701

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7705093235833496

> <JCHEM_POLAR_SURFACE_AREA>
90.19

> <JCHEM_REFRACTIVITY>
97.0924

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5S,10S,13R,14S,15S,16R,17R)-4,7,17-trimethyl-8-oxo-3,9,19-trioxaspiro[hexacyclo[13.3.1.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,10}]nonadecane-13,2'-oxiran]-6-en-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-FEB-23         0                                  
HETATM    1  O   UNK     0      10.101   2.301   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.802   1.474   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.707  -0.064   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.216  -0.449   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       5.687  -0.630   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       6.716  -1.905   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.266  -2.423   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.957  -1.611   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.246  -2.977   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.418  -1.678   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.775  -0.082   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       5.232  -0.582   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       4.858   1.014   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.450   2.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.936   2.906   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.961   2.888   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.043   3.984   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.878   1.793   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.368   1.403   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.286   0.308   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.999  -0.539   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.928  -2.077   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.440  -2.784   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.512  -4.323   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.737  -1.953   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.204   0.423   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.689   0.016   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.340   1.864   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       5.855   2.187   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       6.389   0.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.369   2.038   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.984   3.529   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   30                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8   10                                                       
CONECT   10    9    8                                                       
CONECT   11    8   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14   29   30                                             
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   14                                                       
CONECT   18   16   19   20   28                                             
CONECT   19   18   20                                                       
CONECT   20   18   11   19   21                                             
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   18                                                       
CONECT   29   13                                                            
CONECT   30   13    4   31                                                  
CONECT   31   30    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₇

Average Mass

402.4430 Da

Monoisotopic Mass

402.16785 Da

IUPAC Name

(1S,2S,4S,5S,10S,13R,14S,15S,16R,17R)-4,7,17-trimethyl-8-oxo-3,9,19-trioxaspiro[hexacyclo[13.3.1.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,10}]nonadecane-13,2'-oxiran]-6-en-16-yl acetate

Traditional Name

(1S,2S,4S,5S,10S,13R,14S,15S,16R,17R)-4,7,17-trimethyl-8-oxo-3,9,19-trioxaspiro[hexacyclo[13.3.1.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,10}]nonadecane-13,2'-oxiran]-6-en-16-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@]3(CO3)[C@]3([H])[C@@]([H])(C1=C(C)C(=O)O2)[C@]1(C)O[C@@H]1[C@@]12C[C@@H](C)[C@@H](OC(C)=O)[C@@]31O2

InChI Identifier

InChI=1S/C22H26O7/c1-9-7-21-18-19(4,28-18)14-13-10(2)17(24)27-12(13)5-6-20(8-25-20)15(14)22(21,29-21)16(9)26-11(3)23/h9,12,14-16,18H,5-8H2,1-4H3/t9-,12+,14-,15+,16-,18+,19+,20+,21+,22+/m1/s1

InChI Key

UORZKWLRBDPPDZ-HLXNSTBUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Fatty alcohol ester
Oxepane
Fatty acid ester
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.17	ChemAxon
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	90.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.09 m³·mol⁻¹	ChemAxon
Polarizability	40.82 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

171348901

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Crotokilwaepoxide D (NP0331517)

MOL for NP0331517 (Crotokilwaepoxide D)

3D MOL for NP0331517 (Crotokilwaepoxide D)

3D SDF for NP0331517 (Crotokilwaepoxide D)

3D-SDF for NP0331517 (Crotokilwaepoxide D)

PDB for NP0331517 (Crotokilwaepoxide D)

3D PDB for NP0331517 (Crotokilwaepoxide D)

SMILES for NP0331517 (Crotokilwaepoxide D)

INCHI for NP0331517 (Crotokilwaepoxide D)

Structure for NP0331517 (Crotokilwaepoxide D)

3D Structure for NP0331517 (Crotokilwaepoxide D)