NP-MRD: Showing NP-Card for (2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol (NP0267454)

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Record Information

Version

2.0

Created at

2022-09-08 12:14:16 UTC

Updated at

2022-09-08 12:14:17 UTC

NP-MRD ID

NP0267454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol

Description

(2S,3R,4S,5S)-2-[(1'S,2R,2'R,4'R,5R,7'S,8'S,9'S,12'R,13'S,15'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane]-16'-oloxy]oxane-3,4,5-triol 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. (2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol is found in Dioscorea tokoro. Based on a literature review very few articles have been published on (2S,3R,4S,5S)-2-[(1'S,2R,2'R,4'R,5R,7'S,8'S,9'S,12'R,13'S,15'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane]-16'-oloxy]oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214142D          

 40 46  0  0  1  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  1  0  0  0  0  0  0  0  0  0
    8.0648   -3.0857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9311   -2.2716    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
   10.0743   -2.4249    0.0000 C   0  0  1  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
   11.7215   -2.3290    0.0000 C   0  0  2  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  2  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
   12.6282   -3.7076    0.0000 C   0  0  1  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
   13.9051   -4.3489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2754   -3.6117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0990   -3.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5523   -4.2531    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3759   -4.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1820   -4.9903    0.0000 C   0  0  2  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
   14.3584   -5.0382    0.0000 C   0  0  1  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
   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  1  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  2  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  2  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
    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  2  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  1  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
    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
  2  1  1  6  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  1  0  0  0
  4 33  1  6  0  0  0
 34 33  1  1  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 34 40  1  0  0  0  0
M  END

     RDKit          3D

 92 98  0  0  0  0  0  0  0  0999 V2000
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    4.7279   -0.5324   -1.1286 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5082   -1.0627   -1.6835 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9496    0.1414   -2.4572 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5438   -0.2421   -2.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -1.5306   -1.9096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0960   -1.6538   -1.4065 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.3180   -3.7507   -0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023   -3.0475    0.3218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5720   -3.0221   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0568   -0.7486    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1548    1.1462   -1.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5303    0.9889   -1.2240 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2801    1.5980   -2.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6744    2.0443   -1.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7334    2.8580   -0.7487 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2490    4.2453   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3060    2.9128   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968    1.5944   -0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274   -1.5567    0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5691   -0.7379   -1.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6957   -1.8349   -2.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5795   -0.3274   -0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7247    4.4306    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1503    3.0511    0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9504    4.8130    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8213    2.2983    2.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 38 89  1  0
 38 90  1  0
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 39 92  1  0
M  END


  Mrv1652309082214142D          

 40 46  0  0  1  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  1  0  0  0  0  0  0  0  0  0
    8.0648   -3.0857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9311   -2.2716    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
   10.0743   -2.4249    0.0000 C   0  0  1  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
   11.7215   -2.3290    0.0000 C   0  0  2  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  2  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
   12.6282   -3.7076    0.0000 C   0  0  1  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
   13.9051   -4.3489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2754   -3.6117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0990   -3.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5523   -4.2531    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3759   -4.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1820   -4.9903    0.0000 C   0  0  2  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
   14.3584   -5.0382    0.0000 C   0  0  1  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
   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  1  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  2  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  2  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
    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  2  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  1  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
    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
  2  1  1  6  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  1  0  0  0
  4 33  1  6  0  0  0
 34 33  1  1  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 34 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2[C@@H](C[C@@H]3[C@H]4CC[C@@H]5C[C@H](O)[C@H](C[C@]5(C)[C@@H]4CC[C@]23C)O[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)O[C@]11CC[C@@H](C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C32H52O8/c1-16-7-10-32(38-14-16)17(2)26-24(40-32)12-21-19-6-5-18-11-22(33)25(39-29-28(36)27(35)23(34)15-37-29)13-31(18,4)20(19)8-9-30(21,26)3/h16-29,33-36H,5-15H2,1-4H3/t16-,17+,18-,19+,20-,21-,22+,23+,24-,25+,26-,27+,28-,29+,30+,31+,32-/m1/s1

> <INCHI_KEY>
KKQQPVXVNRLUKV-QGINBHEBSA-N

> <FORMULA>
C32H52O8

> <MOLECULAR_WEIGHT>
564.76

> <EXACT_MASS>
564.366218634

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
62.06039744361042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S)-2-[(1'S,2R,2'R,4'R,5R,7'S,8'S,9'S,12'R,13'S,15'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-16'-oloxy]oxane-3,4,5-triol

> <JCHEM_LOGP>
3.1174806246666655

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.341638651191737

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.241173003363205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.15569268554483

> <JCHEM_POLAR_SURFACE_AREA>
117.84000000000002

> <JCHEM_REFRACTIVITY>
147.22820000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S)-2-[(1'S,2R,2'R,4'R,5R,7'S,8'S,9'S,12'R,13'S,15'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-16'-oloxy]oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         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  C   UNK     0      21.880  -4.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.418  -4.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.264  -5.545   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.801  -5.455   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      23.573  -6.921   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      24.419  -8.208   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      25.956  -8.118   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      26.647  -6.742   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      28.185  -6.652   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.031  -7.939   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      30.568  -7.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      28.340  -9.315   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      29.186 -10.602   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      26.802  -9.405   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      26.111 -10.781   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      22.035  -7.010   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.189  -5.724   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.498  -7.100   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.652  -5.813   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.960  -7.189   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.423  -7.279   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.577  -5.992   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.746  -7.289   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.282  -4.008   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.591  -5.384   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.048  -6.825   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.528  -7.075   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.552  -5.884   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.032  -6.134   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.095  -4.443   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      11.615  -4.193   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23                                                            
CONECT   25   14   26                                                       
CONECT   26   25   10   27   28                                             
CONECT   27   26                                                            
CONECT   28   26    7   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    3    6   32                                             
CONECT   32   31                                                            
CONECT   33    4   34                                                       
CONECT   34   33    2   35   40                                             
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   34                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₅₂O₈

Average Mass

564.7600 Da

Monoisotopic Mass

564.36622 Da

IUPAC Name

(2S,3R,4S,5S)-2-[(1'S,2R,2'R,4'R,5R,7'S,8'S,9'S,12'R,13'S,15'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-16'-oloxy]oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2[C@@H](C[C@@H]3[C@H]4CC[C@@H]5C[C@H](O)[C@H](C[C@]5(C)[C@@H]4CC[C@]23C)O[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)O[C@]11CC[C@@H](C)CO1

InChI Identifier

InChI=1S/C32H52O8/c1-16-7-10-32(38-14-16)17(2)26-24(40-32)12-21-19-6-5-18-11-22(33)25(39-29-28(36)27(35)23(34)15-37-29)13-31(18,4)20(19)8-9-30(21,26)3/h16-29,33-36H,5-15H2,1-4H3/t16-,17+,18-,19+,20-,21-,22+,23+,24-,25+,26-,27+,28-,29+,30+,31+,32-/m1/s1

InChI Key

KKQQPVXVNRLUKV-QGINBHEBSA-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
Dioscorea tokoro	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
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Monosaccharide
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Oxacycle
Polyol
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
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	3.12	ChemAxon
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	117.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	147.23 m³·mol⁻¹	ChemAxon
Polarizability	62.06 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162947496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol (NP0267454)

MOL for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

3D MOL for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

3D SDF for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

3D-SDF for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

PDB for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

3D PDB for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

SMILES for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

INCHI for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

Structure for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)

3D Structure for NP0267454 ((2s,3r,4s,5s)-2-[(1's,2r,2'r,4'r,5r,7's,8's,9's,12'r,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-16'-oloxy]oxane-3,4,5-triol)