NP-MRD: Showing NP-Card for 1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate (NP0151897)

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Record Information

Version

2.0

Created at

2022-09-02 08:17:20 UTC

Updated at

2022-09-02 08:17:20 UTC

NP-MRD ID

NP0151897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate

Description

Stichoposide, also known as holotoxin A1, belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate is found in Stichopus chloronotus. 1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate was first documented in 2015 (PMID: 26318294). Based on a literature review a small amount of articles have been published on Stichoposide (PMID: 35087279) (PMID: 30250516) (PMID: 29416631) (PMID: 28512032).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210172D          

 56 62  0  0  0  0            999 V2000
   -2.6434    0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0207    0.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -0.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2407    0.5465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    0.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7753   -0.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1526   -1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274   -1.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100   -2.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    0.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    0.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468    0.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057    0.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0613   -0.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2024    0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6990   -0.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6921   -1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0144   -1.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6371   -1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9950    3.8993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
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 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 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
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
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 55 56  1  0  0  0  0
 11 56  1  0  0  0  0
 16 56  1  0  0  0  0
M  END

     RDKit          3D

124130  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309022210172D          

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M  END
> <DATABASE_ID>
NP0151897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(CC1(C)OC(=O)C23CCC4C(=CCC5C(C)(C)CC(CC45C)OC4OCC(O)C(O)C4OC4OC(C)C(O)C(O)C4O)C2(C)CCC13)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C43H68O13/c1-21(2)16-24(53-23(4)44)19-42(9)30-13-14-41(8)27-10-11-29-39(5,6)17-25(18-40(29,7)26(27)12-15-43(30,41)38(50)56-42)54-37-35(32(47)28(45)20-51-37)55-36-34(49)33(48)31(46)22(3)52-36/h10,21-22,24-26,28-37,45-49H,11-20H2,1-9H3

> <INCHI_KEY>
LZPPMXGTNICIOQ-UHFFFAOYSA-N

> <FORMULA>
C43H68O13

> <MOLECULAR_WEIGHT>
793.004

> <EXACT_MASS>
792.46599225

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
124

> <JCHEM_AVERAGE_POLARIZABILITY>
86.74486030321708

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
3.6581453603333305

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.787534552528289

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.127001146393434

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5268774542682637

> <JCHEM_POLAR_SURFACE_AREA>
190.67

> <JCHEM_REFRACTIVITY>
202.12020000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.934   1.529   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.772   0.519   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.066  -0.993   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.316   1.020   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.154   0.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.447  -1.502   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.285  -2.512   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.171  -2.011   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.579  -4.024   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.302   0.511   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.465  -0.499   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.339  -1.549   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.348   0.763   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.821   0.313   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.051   1.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.848  -1.227   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.449   0.190   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.978   0.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.905  -0.852   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.303  -2.269   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.230  -3.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.759  -3.311   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.360  -1.894   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.889  -1.706   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.808  -3.244   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.389  -2.052   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.490  -0.288   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.563   0.942   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.165   2.359   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.238   3.589   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.710   3.401   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.783   4.631   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.384   6.049   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.457   7.279   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.913   6.237   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.514   7.654   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.840   5.007   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.368   5.195   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.970   6.612   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.043   7.842   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      12.644   9.260   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.718  10.490   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      14.173   9.448   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      14.775  10.865   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      15.100   8.218   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      16.628   8.406   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      14.498   6.800   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      15.425   5.570   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       9.035   0.754   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.433  -0.664   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.506   0.566   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.775  -2.457   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.568  -3.777   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       3.892  -3.719   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.419  -3.268   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       2.392  -1.729   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   13   56                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   52   56                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   50                                                  
CONECT   20   19   21   52                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   50                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   49                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   47                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   39   48                                                  
CONECT   48   47                                                            
CONECT   49   28   50                                                       
CONECT   50   49   19   23   51                                             
CONECT   51   50                                                            
CONECT   52   20   16   53   54                                             
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   11   16                                                  
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Value	Source
1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0,.0,.0,]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetic acid	HMDB
Holotoxin a1	HMDB
Holotoxin b1	HMDB
Holotoxins	HMDB
Stichoposide a	HMDB
Stichoposide a1	HMDB
Stichoposide C	HMDB

Chemical Formula

C₄₃H₆₈O₁₃

Average Mass

793.0040 Da

Monoisotopic Mass

792.46599 Da

IUPAC Name

1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)CC(CC1(C)OC(=O)C23CCC4C(=CCC5C(C)(C)CC(CC45C)OC4OCC(O)C(O)C4OC4OC(C)C(O)C(O)C4O)C2(C)CCC13)OC(C)=O

InChI Identifier

InChI=1S/C43H68O13/c1-21(2)16-24(53-23(4)44)19-42(9)30-13-14-41(8)27-10-11-29-39(5,6)17-25(18-40(29,7)26(27)12-15-43(30,41)38(50)56-42)54-37-35(32(47)28(45)20-51-37)55-36-34(49)33(48)31(46)22(3)52-36/h10,21-22,24-26,28-37,45-49H,11-20H2,1-9H3

InChI Key

LZPPMXGTNICIOQ-UHFFFAOYSA-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
Stichopus chloronotus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpenoid
Bile acid, alcohol, or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
Oxane
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.35	ALOGPS
logP	3.66	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.67 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	202.12 m³·mol⁻¹	ChemAxon
Polarizability	86.74 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0258497

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

106411

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119095

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu F, Tang L, Tao M, Cui C, He D, Li L, Liao Y, Gao Y, He J, Sun F, Lin H, Li H: Stichoposide C Exerts Anticancer Effects on Ovarian Cancer by Inducing Autophagy via Inhibiting AKT/mTOR Pathway. Onco Targets Ther. 2022 Jan 21;15:87-101. doi: 10.2147/OTT.S340556. eCollection 2022. [PubMed:35087279 ]
Wargasetia TL, Permana S, Widodo N: Potential use of compounds from sea cucumbers as MDM2 and CXCR4 inhibitors to control cancer cell growth. Exp Ther Med. 2018 Oct;16(4):2985-2991. doi: 10.3892/etm.2018.6588. Epub 2018 Aug 7. [PubMed:30250516 ]
Yun SH, Sim EH, Han SH, Kim TR, Ju MH, Han JY, Jeong JS, Kim SH, Silchenko AS, Stonik VA, Park JI: In vitro and in vivo anti-leukemic effects of cladoloside C(2) are mediated by activation of Fas/ceramide synthase 6/p38 kinase/c-Jun NH(2)-terminal kinase/caspase-8. Oncotarget. 2017 Dec 8;9(1):495-511. doi: 10.18632/oncotarget.23069. eCollection 2018 Jan 2. [PubMed:29416631 ]
Cuong NX, Vien LT, Hoang L, Hanh TTH, Thao DT, Thanh NV, Nam NH, Thung DC, Kiem PV, Minh CV: Cytotoxic triterpene diglycosides from the sea cucumber Stichopus horrens. Bioorg Med Chem Lett. 2017 Jul 1;27(13):2939-2942. doi: 10.1016/j.bmcl.2017.05.003. Epub 2017 May 6. [PubMed:28512032 ]
Yun SH, Park ES, Shin SW, Ju MH, Han JY, Jeong JS, Kim SH, Stonik VA, Kwak JY, Park JI: By activating Fas/ceramide synthase 6/p38 kinase in lipid rafts, stichoposide D inhibits growth of leukemia xenografts. Oncotarget. 2015 Sep 29;6(29):27596-612. doi: 10.18632/oncotarget.4820. [PubMed:26318294 ]
LOTUS database [Link]

Showing NP-Card for 1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate (NP0151897)

MOL for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

3D MOL for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

3D SDF for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

3D-SDF for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

PDB for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

3D PDB for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

SMILES for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

INCHI for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

Structure for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)

3D Structure for NP0151897 (1-[15-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]icos-1(20)-en-6-yl]-4-methylpentan-2-yl acetate)