NP-MRD: Showing NP-Card for Volubiloside A (NP0075891)

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Record Information

Version

2.0

Created at

2022-04-28 21:06:15 UTC

Updated at

2022-04-28 21:06:15 UTC

NP-MRD ID

NP0075891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Volubiloside A

Description

(2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-5-hydroxy-4-methoxy-6-{[(2R,3R,4S,6S)-4-methoxy-6-{[(2R,3R,4S,6R)-4-methoxy-2-methyl-6-{[(1S,2R,5S,10R,11S,14S,15S,16S,17S)-11,16,17-trihydroxy-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}oxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Volubiloside A is found in Dregea volubilis and Dregea volubilis L. . Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-5-hydroxy-4-methoxy-6-{[(2R,3R,4S,6S)-4-methoxy-6-{[(2R,3R,4S,6R)-4-methoxy-2-methyl-6-{[(1S,2R,5S,10R,11S,14S,15S,16S,17S)-11,16,17-trihydroxy-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}oxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223062D          

 68 75  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705   -1.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.5148   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7663   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2026   -1.6747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4829   -0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2951   -0.7535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8269   -1.3843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5466   -2.1602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7345   -2.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0784   -2.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6390   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1708   -1.8697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8905   -2.6457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4223   -3.2764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2345   -3.1312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5148   -2.3552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9829   -1.7245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2632   -0.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3269   -2.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6072   -1.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7663   -3.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4860   -4.5378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0178   -5.1685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.7375   -5.9444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9254   -6.0896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3936   -5.4589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6739   -4.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5814   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3011   -6.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6451   -6.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2693   -6.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8299   -5.0233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1420   -4.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5754    0.0224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3875    0.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 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
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  6  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
 13 24  1  1  0  0  0
 12 25  1  6  0  0  0
  2 26  1  1  0  0  0
 27 26  1  6  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
 27 32  1  0  0  0  0
 31 33  1  1  0  0  0
 33 34  1  0  0  0  0
 30 35  1  1  0  0  0
 36 35  1  1  0  0  0
 36 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
 40 41  1  0  0  0  0
 36 41  1  0  0  0  0
 40 42  1  1  0  0  0
 39 43  1  6  0  0  0
 44 43  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 44 49  1  0  0  0  0
 49 50  1  6  0  0  0
 48 51  1  6  0  0  0
 51 52  1  0  0  0  0
 47 53  1  6  0  0  0
 54 53  1  1  0  0  0
 54 55  1  0  0  0  0
 55 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
 54 59  1  0  0  0  0
 58 60  1  1  0  0  0
 60 61  1  0  0  0  0
 57 62  1  1  0  0  0
 56 63  1  1  0  0  0
 55 64  1  6  0  0  0
 46 65  1  1  0  0  0
 38 66  1  6  0  0  0
 66 67  1  0  0  0  0
 29 68  1  6  0  0  0
M  END

     RDKit          3D

148155  0  0  0  0  0  0  0  0999 V2000
    0.9713   -0.1405   -2.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484    0.4480   -1.2551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594    1.7837   -1.4865 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5327    1.9297   -1.5234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115    2.2052   -0.2029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3893    2.9484   -0.4609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4843    2.1699   -0.0760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4474    2.9438    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7277    2.3005    1.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3799    1.5257   -0.0834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0194    2.5587   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3008    0.8152   -0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321   -0.4777   -1.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.6474    0.5216    2.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.4331   -3.0025    2.8776 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.8428   -2.1014    4.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5039   -3.8249    2.5240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4031   -3.4366    0.7099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7346   -2.8199   -0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8088   -1.3523   -0.3713 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282223062D          

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 46 65  1  1  0  0  0
 38 66  1  6  0  0  0
 66 67  1  0  0  0  0
 29 68  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075891

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4[C@H](O)[C@@H](O)[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC=C3C2)[C@@H](C)O)O[C@H](C)[C@H]1O[C@H]1C[C@H](OC)[C@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](OC)[C@H]2O)[C@@H](C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C48H80O20/c1-20(50)26-13-15-48(57)27-11-10-24-16-25(12-14-46(24,5)33(27)35(52)43(56)47(26,48)6)64-31-17-28(58-7)39(21(2)61-31)66-32-18-29(59-8)40(22(3)62-32)67-45-38(55)42(60-9)41(23(4)63-45)68-44-37(54)36(53)34(51)30(19-49)65-44/h10,20-23,25-45,49-57H,11-19H2,1-9H3/t20-,21-,22-,23-,25+,26-,27-,28+,29+,30-,31+,32+,33-,34+,35+,36+,37-,38-,39-,40-,41-,42+,43-,44+,45+,46+,47+,48+/m1/s1

> <INCHI_KEY>
BTLNMUKZJKKYNI-LEUKXYAOSA-N

> <FORMULA>
C48H80O20

> <MOLECULAR_WEIGHT>
977.148

> <EXACT_MASS>
976.524294976

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
148

> <JCHEM_AVERAGE_POLARIZABILITY>
106.10567731972708

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-5-hydroxy-4-methoxy-6-{[(2R,3R,4S,6S)-4-methoxy-6-{[(2R,3R,4S,6R)-4-methoxy-2-methyl-6-{[(1S,2R,5S,10R,11S,14S,15S,16S,17S)-11,16,17-trihydroxy-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}oxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
-0.14720637366666423

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.493286761372058

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.96202124925832

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083565261346

> <JCHEM_POLAR_SURFACE_AREA>
283.59999999999997

> <JCHEM_REFRACTIVITY>
235.29020000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-5-hydroxy-4-methoxy-6-{[(2R,3R,4S,6S)-4-methoxy-6-{[(2R,3R,4S,6R)-4-methoxy-2-methyl-6-{[(1S,2R,5S,10R,11S,14S,15S,16S,17S)-11,16,17-trihydroxy-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}oxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-6-(hydroxymethyl)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  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.558  -2.907   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.932  -2.940   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.964  -2.398   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.067   0.406   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.981  -4.210   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      19.045  -3.126   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      19.568  -1.678   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      21.084  -1.407   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      22.077  -2.584   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.554  -4.032   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      20.038  -4.303   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      22.546  -5.210   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      23.593  -2.313   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      24.586  -3.490   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      24.062  -4.939   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      25.055  -6.116   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      26.571  -5.845   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      27.094  -4.396   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      26.101  -3.219   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      26.625  -1.771   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      28.610  -4.125   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      29.133  -2.677   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      27.564  -7.022   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      27.041  -8.471   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      28.033  -9.648   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      27.510 -11.096   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      25.994 -11.367   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      25.001 -10.190   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      25.525  -8.742   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      23.485 -10.461   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      22.962 -11.909   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      25.471 -12.816   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      28.503 -12.274   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      29.549  -9.377   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      24.532  -7.564   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      21.607   0.042   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      23.123   0.313   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      18.575  -0.500   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13   25                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   18   23                                             
CONECT   15   14    7   16   22                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24   13                                                            
CONECT   25   12                                                            
CONECT   26    2   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   68                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   30   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   66                                                  
CONECT   39   38   40   43                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40   36                                                       
CONECT   42   40                                                            
CONECT   43   39   44                                                       
CONECT   44   43   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   65                                                  
CONECT   47   46   48   53                                                  
CONECT   48   47   49   51                                                  
CONECT   49   48   44   50                                                  
CONECT   50   49                                                            
CONECT   51   48   52                                                       
CONECT   52   51                                                            
CONECT   53   47   54                                                       
CONECT   54   53   55   59                                                  
CONECT   55   54   56   64                                                  
CONECT   56   55   57   63                                                  
CONECT   57   56   58   62                                                  
CONECT   58   57   59   60                                                  
CONECT   59   58   54                                                       
CONECT   60   58   61                                                       
CONECT   61   60                                                            
CONECT   62   57                                                            
CONECT   63   56                                                            
CONECT   64   55                                                            
CONECT   65   46                                                            
CONECT   66   38   67                                                       
CONECT   67   66                                                            
CONECT   68   29                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  150    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₈H₈₀O₂₀

Average Mass

977.1480 Da

Monoisotopic Mass

976.52429 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4[C@H](O)[C@@H](O)[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC=C3C2)[C@@H](C)O)O[C@H](C)[C@H]1O[C@H]1C[C@H](OC)[C@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](OC)[C@H]2O)[C@@H](C)O1

InChI Identifier

InChI=1S/C48H80O20/c1-20(50)26-13-15-48(57)27-11-10-24-16-25(12-14-46(24,5)33(27)35(52)43(56)47(26,48)6)64-31-17-28(58-7)39(21(2)61-31)66-32-18-29(59-8)40(22(3)62-32)67-45-38(55)42(60-9)41(23(4)63-45)68-44-37(54)36(53)34(51)30(19-49)65-44/h10,20-23,25-45,49-57H,11-19H2,1-9H3/t20-,21-,22-,23-,25+,26-,27-,28+,29+,30-,31+,32+,33-,34+,35+,36+,37-,38-,39-,40-,41-,42+,43-,44+,45+,46+,47+,48+/m1/s1

InChI Key

BTLNMUKZJKKYNI-LEUKXYAOSA-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
Dregea volubilis	LOTUS Database	35616633
Dregea volubilis L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
Oligosaccharide
Pregnane-skeleton
20-hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Hydroxysteroid
14-hydroxysteroid
12-hydroxysteroid
Delta-5-steroid
O-glycosyl compound
Glycosyl compound
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
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	0.31	ALOGPS
logP	-0.15	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	283.6 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	235.29 m³·mol⁻¹	ChemAxon
Polarizability	106.11 Å³	ChemAxon
Number of Rings	8	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

162895812

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Volubiloside A (NP0075891)

MOL for NP0075891 (Volubiloside A)

3D MOL for NP0075891 (Volubiloside A)

3D SDF for NP0075891 (Volubiloside A)

3D-SDF for NP0075891 (Volubiloside A)

PDB for NP0075891 (Volubiloside A)

3D PDB for NP0075891 (Volubiloside A)

SMILES for NP0075891 (Volubiloside A)

INCHI for NP0075891 (Volubiloside A)

Structure for NP0075891 (Volubiloside A)

3D Structure for NP0075891 (Volubiloside A)