NP-MRD: Showing NP-Card for (-)-Sachaloside II (NP0071776)

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Record Information

Version

2.0

Created at

2022-04-28 17:06:56 UTC

Updated at

2022-04-28 17:06:56 UTC

NP-MRD ID

NP0071776

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Sachaloside II

Description

(2R,3R,4S,5S,6R)-2-{[(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]Heptan-3-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (-)-Sachaloside II is found in Rhodiola crenulata and Rhodiola sachalinensis . Based on a literature review very few articles have been published on (2R,3R,4S,5S,6R)-2-{[(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]Heptan-3-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219062D          

 31 34  0  0  1  0            999 V2000
    3.2433    0.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558    1.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2433    2.0769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6558    2.7914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4808    2.7914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8933    2.0769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4808    1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7183    2.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1308    2.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9558    2.7914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3683    3.5059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1933    3.5059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6058    2.7914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1933    2.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3683    2.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4308    2.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6058    4.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9558    4.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933    3.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2433    3.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    2.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    0.6480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0058   -0.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -0.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -0.0665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7683    0.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808    1.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0058    1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3594    0.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399    0.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399    1.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  2  7  1  0  0  0  0
  6  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  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  1  0  0  0
 12 17  1  6  0  0  0
 11 18  1  6  0  0  0
  5 19  1  6  0  0  0
  4 20  1  1  0  0  0
  3 21  1  6  0  0  0
 22  1  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 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
 22 28  1  0  0  0  0
 27 29  1  6  0  0  0
 25 29  1  6  0  0  0
 26 30  1  0  0  0  0
 26 31  1  0  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
   -4.4093   -2.1356    0.8525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4109   -0.8728    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1946   -0.0609    0.2145 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1521   -0.7696   -0.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9494   -0.6713    0.3751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0476   -0.0641   -0.4135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3141   -0.1869   -0.0083 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0567    0.8860   -0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3278    1.1236   -0.5368 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4196    0.4838   -0.8814 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3137    1.3088   -1.6443 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5165    0.6253   -1.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3553    0.7318   -0.5876 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9778   -0.4861   -0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662    1.0372    0.5205 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8626    2.3415    0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2159    0.0984    0.3750 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3239    0.2115    1.4660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -1.6168   -0.2136 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9086   -2.0461   -0.0806 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475   -2.3398    0.9272 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1390   -3.6897    0.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -2.0202    0.8992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0698   -2.1578    2.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5091    1.0924   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9642    1.4028   -0.7844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7750    0.1654   -1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7251   -0.2080    0.2925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6828    1.2851    0.5452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9504    1.7488    1.7546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1029    1.8289    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3090   -2.6751    1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597   -2.6303    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7880    0.4061    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796   -0.0183    1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2759    0.0742    1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    1.8597   -0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325    0.9273   -1.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871   -0.4628   -1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3510   -0.4409   -2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0618    1.1382   -2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0988    1.5573   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9017   -0.5326   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8544    0.9927    1.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5473    2.9135   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -0.9683    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7402   -0.3149    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252   -1.9921   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277   -2.8824   -0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -1.9351    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4329   -4.0089   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130   -2.8150    0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359   -1.2481    2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772    0.8394   -1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9629    1.9931   -0.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1820    2.2962   -1.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8065    0.4331   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2375   -0.5149   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6040   -0.7368    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6399    2.4342    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0979    2.3837    1.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7054    0.9447    2.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2582    2.6736    1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2922    2.2183   -0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8615    1.0450    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  1
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  7 19  1  0
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 28 29  1  0
 23  5  1  0
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 17 10  1  0
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 31 63  1  0
 31 64  1  0
 31 65  1  0
 26 56  1  6
 27 57  1  0
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  1 32  1  0
  1 33  1  0
  3 34  1  1
 25 54  1  0
 25 55  1  0
  5 35  1  1
  7 36  1  1
  8 37  1  0
  8 38  1  0
 10 39  1  6
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 12 41  1  0
 13 42  1  6
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 15 44  1  1
 16 45  1  0
 17 46  1  6
 18 47  1  0
 19 48  1  6
 20 49  1  0
 21 50  1  1
 22 51  1  0
 23 52  1  6
 24 53  1  0
M  END


  Mrv1652304282219062D          

 31 34  0  0  1  0            999 V2000
    3.2433    0.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558    1.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2433    2.0769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6558    2.7914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4808    2.7914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8933    2.0769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4808    1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7183    2.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1308    2.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9558    2.7914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3683    3.5059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1933    3.5059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6058    2.7914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1933    2.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3683    2.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4308    2.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6058    4.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9558    4.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933    3.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2433    3.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    2.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183    0.6480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0058   -0.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -0.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -0.0665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7683    0.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808    1.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0058    1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3594    0.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399    0.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399    1.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  2  7  1  0  0  0  0
  6  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  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  1  0  0  0
 12 17  1  6  0  0  0
 11 18  1  6  0  0  0
  5 19  1  6  0  0  0
  4 20  1  1  0  0  0
  3 21  1  6  0  0  0
 22  1  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 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
 22 28  1  0  0  0  0
 27 29  1  6  0  0  0
 25 29  1  6  0  0  0
 26 30  1  0  0  0  0
 26 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071776

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2C[C@H]1C(=C)[C@H](C2)O[C@@H]1O[C@H](CO[C@H]2OC[C@H](O)[C@@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O10/c1-8-10-4-9(21(10,2)3)5-12(8)30-20-18(27)16(25)15(24)13(31-20)7-29-19-17(26)14(23)11(22)6-28-19/h9-20,22-27H,1,4-7H2,2-3H3/t9-,10+,11+,12+,13-,14-,15-,16+,17-,18-,19-,20-/m1/s1

> <INCHI_KEY>
BAWFMLVRUDRUAA-JCIZUSNUSA-N

> <FORMULA>
C21H34O10

> <MOLECULAR_WEIGHT>
446.493

> <EXACT_MASS>
446.215197295

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.16740265219955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.82

> <JCHEM_LOGP>
-1.2825522996666663

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.461735462000927

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.92784235190337

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526580404084756

> <JCHEM_POLAR_SURFACE_AREA>
158.3

> <JCHEM_REFRACTIVITY>
104.02939999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       6.054   1.210   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.824   2.543   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.054   3.877   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.824   5.211   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.364   5.211   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.134   3.877   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.364   2.543   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.674   3.877   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.444   5.211   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.984   5.211   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.754   6.544   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.294   6.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.064   5.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.294   3.877   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.754   3.877   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      17.604   5.211   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      16.064   7.878   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.984   7.878   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.134   6.544   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.054   6.544   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.514   3.877   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.514   1.210   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.744  -0.124   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.514  -1.458   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.204  -0.124   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.434   1.210   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.204   2.543   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.744   2.543   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.538   1.210   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.074   0.487   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.074   1.933   0.000  0.00  0.00           C+0
CONECT    1    2   22                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13                                                            
CONECT   17   12                                                            
CONECT   18   11                                                            
CONECT   19    5                                                            
CONECT   20    4                                                            
CONECT   21    3                                                            
CONECT   22    1   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   29                                                  
CONECT   26   25   27   30   31                                             
CONECT   27   26   28   29                                                  
CONECT   28   27   22                                                       
CONECT   29   27   25                                                       
CONECT   30   26                                                            
CONECT   31   26                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₄O₁₀

Average Mass

446.4930 Da

Monoisotopic Mass

446.21520 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2C[C@H]1C(=C)[C@H](C2)O[C@@H]1O[C@H](CO[C@H]2OC[C@H](O)[C@@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H34O10/c1-8-10-4-9(21(10,2)3)5-12(8)30-20-18(27)16(25)15(24)13(31-20)7-29-19-17(26)14(23)11(22)6-28-19/h9-20,22-27H,1,4-7H2,2-3H3/t9-,10+,11+,12+,13-,14-,15-,16+,17-,18-,19-,20-/m1/s1

InChI Key

BAWFMLVRUDRUAA-JCIZUSNUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhodiola crenulata	Plant	KNApSAcK
Rhodiola sachalinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Monoterpenoid
Nopinane monoterpenoid
Pinane monoterpenoid
Bicyclic monoterpenoid
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	-0.82	ALOGPS
logP	-1.3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	11.93	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.03 m³·mol⁻¹	ChemAxon
Polarizability	46.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

162975944

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Sachaloside II (NP0071776)

MOL for NP0071776 ((-)-Sachaloside II)

3D MOL for NP0071776 ((-)-Sachaloside II)

3D SDF for NP0071776 ((-)-Sachaloside II)

3D-SDF for NP0071776 ((-)-Sachaloside II)

PDB for NP0071776 ((-)-Sachaloside II)

3D PDB for NP0071776 ((-)-Sachaloside II)

SMILES for NP0071776 ((-)-Sachaloside II)

INCHI for NP0071776 ((-)-Sachaloside II)

Structure for NP0071776 ((-)-Sachaloside II)

3D Structure for NP0071776 ((-)-Sachaloside II)