NP-MRD: Showing NP-Card for 16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one (NP0255805)

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Record Information

Version

1.0

Created at

2022-09-07 20:25:46 UTC

Updated at

2022-09-07 20:25:46 UTC

NP-MRD ID

NP0255805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one

Description

16'-[(3,4-Dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane]-19'-one belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. 16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one is found in Smilax sieboldii. 16'-[(3,4-Dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane]-19'-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514522D          

 63 71  0  0  0  0            999 V2000
    7.2076   -4.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319   -3.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0648   -3.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9311   -2.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6640   -1.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507   -2.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0743   -2.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4446   -1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2682   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6385   -0.9025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7215   -2.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5451   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9984   -2.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6282   -3.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8046   -3.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -3.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9810   -3.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5276   -3.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1573   -3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3337   -3.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8804   -3.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4351   -3.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8221   -2.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2754   -3.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0990   -3.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5523   -4.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3759   -4.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8292   -4.8944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6528   -4.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0231   -4.1092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8467   -4.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3000   -4.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1237   -4.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9298   -5.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3831   -6.1771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1062   -5.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7359   -6.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1820   -4.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6353   -5.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2651   -6.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4415   -6.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0712   -7.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2476   -7.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8773   -7.9872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5245   -7.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1542   -8.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3481   -7.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8014   -8.5326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -7.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5420   -7.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3584   -5.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9881   -5.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9051   -4.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0815   -4.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -2.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7452   -2.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4540   -3.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -3.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3030   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0118   -4.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2223   -2.2464    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
  3  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 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
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 26 38  1  0  0  0  0
 38 39  1  0  0  0  0
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 41 42  1  0  0  0  0
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 42 45  1  0  0  0  0
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 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 40 49  1  0  0  0  0
 49 50  1  0  0  0  0
 38 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 24 53  1  0  0  0  0
 53 54  1  0  0  0  0
  4 55  1  0  0  0  0
 55 56  1  0  0  0  0
  2 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 59 62  1  0  0  0  0
 62 63  1  0  0  0  0
 56 63  1  0  0  0  0
M  END

     RDKit          3D

133141  0  0  0  0  0  0  0  0999 V2000
    7.8948   -1.1639    2.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4790   -1.3961    1.4524 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1172   -1.9974    1.2751 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2563   -2.6294   -0.1072 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5602   -1.5656   -0.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3812   -1.3112   -0.1489 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5122   -0.1567   -0.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2269   -0.1402   -1.9276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1869   -1.0672   -2.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2045   -1.4915   -3.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391   -1.4547   -1.3854 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1257   -1.5930   -2.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3733   -1.6811   -1.3263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0663   -0.5023   -1.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6489    1.1843    0.2529 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.0660    1.7792    3.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3072   -3.5966    1.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7802   -3.6375    0.0843 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6709   -5.0286   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2639   -0.7221   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3828   -2.0572   -1.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004191514522D          

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M  END
> <DATABASE_ID>
NP0255805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CC(=O)C5CC(CCC5(C)C4CCC23C)OC2OC(COC3OCC(O)C(O)C3O)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11CCC(CO)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C44H70O19/c1-18-30-27(63-44(18)9-4-19(13-45)15-58-44)12-23-21-11-25(47)24-10-20(5-7-42(24,2)22(21)6-8-43(23,30)3)59-40-37(55)34(52)38(62-41-36(54)33(51)32(50)28(14-46)60-41)29(61-40)17-57-39-35(53)31(49)26(48)16-56-39/h18-24,26-41,45-46,48-55H,4-17H2,1-3H3

> <INCHI_KEY>
OQVGNXWQKHWAAQ-UHFFFAOYSA-N

> <FORMULA>
C44H70O19

> <MOLECULAR_WEIGHT>
903.025

> <EXACT_MASS>
902.451130034

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
133

> <JCHEM_AVERAGE_POLARIZABILITY>
97.53480528541236

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-19'-one

> <ALOGPS_LOGP>
-1.09

> <JCHEM_LOGP>
-1.6676594926666632

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.216134446595623

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.766916628038954

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526580404084765

> <JCHEM_POLAR_SURFACE_AREA>
293.21

> <JCHEM_REFRACTIVITY>
213.19050000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-19'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      13.454  -7.989   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.686  -6.467   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.054  -5.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.805  -4.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.173  -3.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.268  -4.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.805  -4.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.497  -3.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.034  -3.061   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      21.725  -1.685   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      21.880  -4.347   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.418  -4.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.264  -5.545   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.573  -6.921   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.035  -7.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.189  -5.724   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.498  -7.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.652  -5.813   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.960  -7.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.423  -7.279   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.577  -5.992   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.746  -7.289   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.801  -5.455   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      26.647  -6.742   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      28.185  -6.652   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      29.031  -7.939   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.568  -7.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      31.415  -9.136   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      32.952  -9.047   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      33.643  -7.671   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      35.181  -7.581   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      36.027  -8.868   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      37.564  -8.778   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      35.336 -10.244   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      36.182 -11.531   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      33.798 -10.333   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      33.107 -11.710   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      28.340  -9.315   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      29.186 -10.602   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      28.495 -11.978   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      26.957 -12.068   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      26.266 -13.444   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      24.729 -13.533   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      24.038 -14.909   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      27.112 -14.730   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      26.421 -16.107   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      28.650 -14.641   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      29.496 -15.928   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      29.341 -13.265   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      30.878 -13.175   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      26.802  -9.405   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      26.111 -10.781   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      25.956  -8.118   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      24.419  -8.208   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      13.282  -4.008   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      12.591  -5.384   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      12.048  -6.825   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.528  -7.075   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       9.552  -5.884   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       8.032  -6.134   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       7.489  -7.574   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      10.095  -4.443   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      11.615  -4.193   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   56                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   55                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17   18                                             
CONECT   17   16                                                            
CONECT   18   16    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    3    6   22                                             
CONECT   22   21                                                            
CONECT   23   13   24                                                       
CONECT   24   23   25   53                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   38                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29   37                                                  
CONECT   37   36                                                            
CONECT   38   26   39   51                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   49                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
CONECT   45   42   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   40   50                                                  
CONECT   50   49                                                            
CONECT   51   38   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   24   54                                                  
CONECT   54   53                                                            
CONECT   55    4   56                                                       
CONECT   56   55    2   57   63                                             
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60   62                                                  
CONECT   60   59   61                                                       
CONECT   61   60                                                            
CONECT   62   59   63                                                       
CONECT   63   62   56                                                       
MASTER        0    0    0    0    0    0    0    0   63    0  142    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₇₀O₁₉

Average Mass

903.0250 Da

Monoisotopic Mass

902.45113 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CC(=O)C5CC(CCC5(C)C4CCC23C)OC2OC(COC3OCC(O)C(O)C3O)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11CCC(CO)CO1

InChI Identifier

InChI=1S/C44H70O19/c1-18-30-27(63-44(18)9-4-19(13-45)15-58-44)12-23-21-11-25(47)24-10-20(5-7-42(24,2)22(21)6-8-43(23,30)3)59-40-37(55)34(52)38(62-41-36(54)33(51)32(50)28(14-46)60-41)29(61-40)17-57-39-35(53)31(49)26(48)16-56-39/h18-24,26-41,45-46,48-55H,4-17H2,1-3H3

InChI Key

OQVGNXWQKHWAAQ-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
Smilax sieboldii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Substituents

Steroidal saponin
Triterpenoid
Spirostane skeleton
Oligosaccharide
Oxosteroid
6-oxosteroid
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Tetrahydrofuran
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Carbonyl group
Organic oxide
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	-1.1	ALOGPS
logP	-1.7	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.77	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	293.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	213.19 m³·mol⁻¹	ChemAxon
Polarizability	97.53 Å³	ChemAxon
Number of Rings	9	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

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

LOTUS database [Link]

Showing NP-Card for 16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one (NP0255805)

MOL for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

3D MOL for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

3D SDF for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

3D-SDF for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

PDB for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

3D PDB for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

SMILES for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

INCHI for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

Structure for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)

3D Structure for NP0255805 (16'-[(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-19'-one)