NP-MRD: Showing NP-Card for sitoindoside IX (NP0036400)

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Record Information

Version

2.0

Created at

2021-06-20 19:34:58 UTC

Updated at

2021-06-30 00:08:02 UTC

NP-MRD ID

NP0036400

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sitoindoside IX

Provided By

JEOL Database JEOL Logo

Description

Sitoindoside IX belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. sitoindoside IX is found in Physalis longifolia and Withania somnifera. sitoindoside IX was first documented in 2003 (PMID: 14575818). Based on a literature review very few articles have been published on sitoindoside IX.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121353D          

 93 99  0  0  0  0            999 V2000
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   -4.8808    1.1299    2.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4660    2.8136    3.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121353D          

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M  END
> <DATABASE_ID>
NP0036400

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC([H])([H])C2=C(C([H])([H])[H])C([H])([H])[C@@]([H])(OC2=O)[C@@]([H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]3([H])[C@]4([H])C([H])([H])[C@@]5([H])O[C@]55[C@@]([H])(O[H])C([H])=C([H])C(=O)[C@]5(C([H])([H])[H])[C@@]4([H])C([H])([H])C([H])([H])[C@]23C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O11/c1-15-11-22(43-30(41)18(15)14-42-31-29(40)28(39)27(38)23(13-35)44-31)16(2)19-5-6-20-17-12-26-34(45-26)25(37)8-7-24(36)33(34,4)21(17)9-10-32(19,20)3/h7-8,16-17,19-23,25-29,31,35,37-40H,5-6,9-14H2,1-4H3/t16-,17-,19+,20-,21-,22+,23+,25-,26+,27+,28-,29+,31+,32+,33-,34+/m0/s1

> <INCHI_KEY>
WKCJIGSUKSPCKI-WNXUODGFSA-N

> <FORMULA>
C34H48O11

> <MOLECULAR_WEIGHT>
632.747

> <EXACT_MASS>
632.319662366

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
66.62807630487816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-2,16-dimethyl-15-[(1S)-1-[(2R)-4-methyl-6-oxo-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,6-dihydro-2H-pyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.8111384686666647

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.028719456631002

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.185832211362158

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083553717509

> <JCHEM_POLAR_SURFACE_AREA>
175.51

> <JCHEM_REFRACTIVITY>
159.60799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-2,16-dimethyl-15-[(1S)-1-[(2R)-4-methyl-6-oxo-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 93 99  0  0  0  0  0  0  0  0999 V2000
   -5.9848    2.1391    2.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8808    1.1299    2.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465    1.3944    3.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447    2.7227    3.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640    3.5495    2.6492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483    3.0926    2.0349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4660    2.8136    3.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7816    2.3591    2.4837 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6619    1.9072    3.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1454    0.7000    4.2172 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4082    3.5021    1.6814 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6865    3.1852    1.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517    3.8739    0.5451 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9565    5.0105   -0.1769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524    4.1924    1.0684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8300    4.3334   -0.0631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736    0.2776    3.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6953    0.3592    4.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9197   -0.8461    2.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052   -0.8180    1.6145 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9897   -2.2392    1.0045 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0388   -2.2997   -0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5728   -2.7875    0.6358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5409   -4.2744    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2222   -4.4593   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945   -3.1277   -0.4194 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6762   -2.7894   -1.3616 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7486   -3.8795   -1.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9840   -3.5480   -2.0087 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7702   -2.9657   -3.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923   -2.1143   -2.2830 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8410   -1.8383   -2.6229 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9614   -1.5344   -4.0073 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4669   -0.7124   -1.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7909    0.1522   -1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168    0.0844   -0.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    0.9039   -0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -0.9302   -1.8556 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0528   -0.1612   -3.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2744   -1.4010   -0.9680 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1413   -0.3425   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -0.7525    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6415   -2.0856   -0.4033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3287   -1.9157   -1.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1986   -0.2535    2.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7007    3.1433    2.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2931    2.2141    1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8516    1.8313    3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896    2.6351    4.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9630    3.2723    4.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6751    2.1831    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919    1.4863    1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862    2.6599    4.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852    1.6991    3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    0.8019    4.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549    4.3808    2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273    2.3197    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    3.0627   -0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9229    4.8668   -0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9503    5.1620    1.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    5.0007   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5627   -0.1343    0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3490   -2.9067    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9194   -1.4877   -0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0242   -3.2478   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0454   -2.2047    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0202   -2.7841    1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3797   -4.5517   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5730   -4.9341    1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4272   -4.6700   -1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6436   -5.2978   -0.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -3.1578    0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3198   -2.7462   -2.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3539   -4.8293   -1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -4.0455   -0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415   -4.3163   -1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4388   -2.7382   -2.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3562   -2.1475   -4.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5439   -0.6049   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863    0.9563   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9018    0.0824   -3.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469   -0.7502   -3.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800    0.7954   -2.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6588   -1.5186    0.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5210    0.6134   -0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2590   -0.1392   -1.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6440   -0.8180    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    0.0578    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9198   -2.7896   -2.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9985   -1.0501   -1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6152   -1.7452   -2.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9658   -0.1896    1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -0.8740    3.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
 43 42  1  0
 42 41  1  0
 43 26  1  0
  9 10  1  0
 35 34  2  0
  6 15  1  0
 15 13  1  0
 13 11  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 43  1  0
 11  8  1  0
 23 21  1  0
 35 36  1  0
 21 20  1  0
 20 19  1  0
 34 32  1  0
 32 31  1  0
 38 36  1  0
 38 31  1  0
  8  7  1  0
 20 45  1  0
 19 17  1  0
 17  3  1  0
  3  2  2  0
  2 45  1  0
  7  6  1  0
 17 18  2  0
  2  1  1  0
 11 12  1  0
  3  4  1  0
  4  5  1  0
 38 40  1  0
 36 37  2  0
 31 29  1  0
 32 33  1  0
 29 28  1  0
 31 30  1  6
 29 30  1  0
 28 27  1  0
 27 73  1  6
 40 27  1  0
 43 44  1  6
 13 14  1  0
 20 62  1  6
 15 16  1  0
 21 22  1  0
 23 67  1  1
 26 72  1  1
 40 41  1  0
 40 84  1  1
 27 26  1  0
 38 39  1  6
  8  9  1  0
  6  5  1  0
 12 57  1  0
  6 51  1  6
 11 56  1  1
 13 58  1  6
 14 59  1  0
 15 60  1  1
 16 61  1  0
  9 53  1  0
  9 54  1  0
  8 52  1  6
 10 55  1  0
 35 80  1  0
 34 79  1  0
 32 77  1  6
 29 76  1  6
 28 74  1  0
 28 75  1  0
 42 87  1  0
 42 88  1  0
 41 85  1  0
 41 86  1  0
 25 70  1  0
 25 71  1  0
 24 68  1  0
 24 69  1  0
 21 63  1  1
 45 92  1  0
 45 93  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  4 49  1  0
  4 50  1  0
 33 78  1  0
 44 89  1  0
 44 90  1  0
 44 91  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 39 81  1  0
 39 82  1  0
 39 83  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.985   2.139   2.582  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.881   1.130   2.726  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.647   1.394   3.215  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.145   2.723   3.713  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.664   3.550   2.649  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.448   3.093   2.035  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.466   2.814   3.031  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.782   2.359   2.484  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.662   1.907   3.651  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.145   0.700   4.217  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.408   3.502   1.681  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.687   3.185   1.128  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.452   3.874   0.545  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.957   5.011  -0.177  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.952   4.192   1.068  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.830   4.333  -0.063  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.674   0.278   3.380  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.695   0.359   4.113  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.920  -0.846   2.667  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.905  -0.818   1.615  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.990  -2.239   1.004  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.039  -2.300  -0.108  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.573  -2.788   0.636  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.541  -4.274   0.187  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.222  -4.459  -0.591  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.495  -3.128  -0.419  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.676  -2.789  -1.362  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.749  -3.880  -1.258  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.984  -3.548  -2.009  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.770  -2.966  -3.289  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.392  -2.114  -2.283  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.841  -1.838  -2.623  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.961  -1.534  -4.007  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.467  -0.712  -1.885  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.791   0.152  -1.125  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.317   0.084  -1.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.791   0.904  -0.240  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.505  -0.930  -1.856  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.053  -0.161  -3.118  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.274  -1.401  -0.968  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.141  -0.343  -0.888  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.014  -0.753   0.030  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.642  -2.086  -0.403  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.329  -1.916  -1.777  0.00  0.00           C+0
HETATM   45  C   UNK     0      -5.199  -0.254   2.197  0.00  0.00           C+0
HETATM   46  H   UNK     0      -5.701   3.143   2.905  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.293   2.214   1.534  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.852   1.831   3.176  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.390   2.635   4.502  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.963   3.272   4.191  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.675   2.183   1.466  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.592   1.486   1.846  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.686   2.660   4.445  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.685   1.699   3.326  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.171   0.802   4.303  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.555   4.381   2.322  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.627   2.320   0.660  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.405   3.063  -0.192  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.923   4.867  -0.243  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.950   5.162   1.582  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.397   5.001  -0.632  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.563  -0.134   0.832  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.349  -2.907   1.802  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.919  -1.488  -0.830  0.00  0.00           H+0
HETATM   65  H   UNK     0      -5.024  -3.248  -0.650  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.045  -2.205   0.314  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.020  -2.784   1.589  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.380  -4.552  -0.456  0.00  0.00           H+0
HETATM   69  H   UNK     0      -2.573  -4.934   1.062  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.427  -4.670  -1.646  0.00  0.00           H+0
HETATM   71  H   UNK     0      -0.644  -5.298  -0.190  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.056  -3.158   0.593  0.00  0.00           H+0
HETATM   73  H   UNK     0       0.320  -2.746  -2.397  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.354  -4.829  -1.637  0.00  0.00           H+0
HETATM   75  H   UNK     0       2.019  -4.045  -0.208  0.00  0.00           H+0
HETATM   76  H   UNK     0       3.741  -4.316  -1.919  0.00  0.00           H+0
HETATM   77  H   UNK     0       5.439  -2.738  -2.436  0.00  0.00           H+0
HETATM   78  H   UNK     0       4.356  -2.147  -4.466  0.00  0.00           H+0
HETATM   79  H   UNK     0       6.544  -0.605  -1.983  0.00  0.00           H+0
HETATM   80  H   UNK     0       5.286   0.956  -0.592  0.00  0.00           H+0
HETATM   81  H   UNK     0       2.902   0.082  -3.765  0.00  0.00           H+0
HETATM   82  H   UNK     0       1.347  -0.750  -3.713  0.00  0.00           H+0
HETATM   83  H   UNK     0       1.580   0.795  -2.869  0.00  0.00           H+0
HETATM   84  H   UNK     0       1.659  -1.519   0.058  0.00  0.00           H+0
HETATM   85  H   UNK     0       0.521   0.613  -0.522  0.00  0.00           H+0
HETATM   86  H   UNK     0      -0.259  -0.139  -1.887  0.00  0.00           H+0
HETATM   87  H   UNK     0      -0.644  -0.818   1.060  0.00  0.00           H+0
HETATM   88  H   UNK     0      -1.746   0.058   0.004  0.00  0.00           H+0
HETATM   89  H   UNK     0      -2.920  -2.790  -2.066  0.00  0.00           H+0
HETATM   90  H   UNK     0      -2.999  -1.050  -1.768  0.00  0.00           H+0
HETATM   91  H   UNK     0      -1.615  -1.745  -2.587  0.00  0.00           H+0
HETATM   92  H   UNK     0      -5.966  -0.190   1.419  0.00  0.00           H+0
HETATM   93  H   UNK     0      -5.583  -0.874   3.014  0.00  0.00           H+0
CONECT    1    2   46   47   48                                             
CONECT    2    3   45    1                                                  
CONECT    3   17    2    4                                                  
CONECT    4    3    5   49   50                                             
CONECT    5    4    6                                                       
CONECT    6   15    7    5   51                                             
CONECT    7    8    6                                                       
CONECT    8   11    7    9   52                                             
CONECT    9   10    8   53   54                                             
CONECT   10    9   55                                                       
CONECT   11   13    8   12   56                                             
CONECT   12   11   57                                                       
CONECT   13   15   11   14   58                                             
CONECT   14   13   59                                                       
CONECT   15    6   13   16   60                                             
CONECT   16   15   61                                                       
CONECT   17   19    3   18                                                  
CONECT   18   17                                                            
CONECT   19   20   17                                                       
CONECT   20   21   19   45   62                                             
CONECT   21   23   20   22   63                                             
CONECT   22   21   64   65   66                                             
CONECT   23   24   43   21   67                                             
CONECT   24   25   23   68   69                                             
CONECT   25   26   24   70   71                                             
CONECT   26   43   25   72   27                                             
CONECT   27   28   73   40   26                                             
CONECT   28   29   27   74   75                                             
CONECT   29   31   28   30   76                                             
CONECT   30   31   29                                                       
CONECT   31   32   38   29   30                                             
CONECT   32   34   31   33   77                                             
CONECT   33   32   78                                                       
CONECT   34   35   32   79                                                  
CONECT   35   34   36   80                                                  
CONECT   36   35   38   37                                                  
CONECT   37   36                                                            
CONECT   38   36   31   40   39                                             
CONECT   39   38   81   82   83                                             
CONECT   40   38   27   41   84                                             
CONECT   41   42   40   85   86                                             
CONECT   42   43   41   87   88                                             
CONECT   43   42   26   23   44                                             
CONECT   44   43   89   90   91                                             
CONECT   45   20    2   92   93                                             
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    4                                                            
CONECT   50    4                                                            
CONECT   51    6                                                            
CONECT   52    8                                                            
CONECT   53    9                                                            
CONECT   54    9                                                            
CONECT   55   10                                                            
CONECT   56   11                                                            
CONECT   57   12                                                            
CONECT   58   13                                                            
CONECT   59   14                                                            
CONECT   60   15                                                            
CONECT   61   16                                                            
CONECT   62   20                                                            
CONECT   63   21                                                            
CONECT   64   22                                                            
CONECT   65   22                                                            
CONECT   66   22                                                            
CONECT   67   23                                                            
CONECT   68   24                                                            
CONECT   69   24                                                            
CONECT   70   25                                                            
CONECT   71   25                                                            
CONECT   72   26                                                            
CONECT   73   27                                                            
CONECT   74   28                                                            
CONECT   75   28                                                            
CONECT   76   29                                                            
CONECT   77   32                                                            
CONECT   78   33                                                            
CONECT   79   34                                                            
CONECT   80   35                                                            
CONECT   81   39                                                            
CONECT   82   39                                                            
CONECT   83   39                                                            
CONECT   84   40                                                            
CONECT   85   41                                                            
CONECT   86   41                                                            
CONECT   87   42                                                            
CONECT   88   42                                                            
CONECT   89   44                                                            
CONECT   90   44                                                            
CONECT   91   44                                                            
CONECT   92   45                                                            
CONECT   93   45                                                            
MASTER        0    0    0    0    0    0    0    0   93    0  198    0
END

RDKit          3D

93 99  0  0  0  0  0  0  0  0999 V2000
   -5.9848    2.1391    2.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8808    1.1299    2.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465    1.3944    3.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447    2.7227    3.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640    3.5495    2.6492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483    3.0926    2.0349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4660    2.8136    3.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7816    2.3591    2.4837 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6619    1.9072    3.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1454    0.7000    4.2172 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4082    3.5021    1.6814 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6865    3.1852    1.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517    3.8739    0.5451 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9565    5.0105   -0.1769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524    4.1924    1.0684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8300    4.3334   -0.0631 O   0  0  0  0  0  0  0  0  0  0  0  0
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 44 91  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 39 81  1  0
 39 82  1  0
 39 83  1  0
M  END

View in JSmol

Synonyms

Value	Source
27-O-beta-D-Glucopyranosylwithaferin a	ChEBI
27-O-b-D-Glucopyranosylwithaferin a	Generator
27-O-Β-D-glucopyranosylwithaferin a	Generator

Chemical Formula

C₃₄H₄₈O₁₁

Average Mass

632.7470 Da

Monoisotopic Mass

632.31966 Da

IUPAC Name

(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-2,16-dimethyl-15-[(1S)-1-[(2R)-4-methyl-6-oxo-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,6-dihydro-2H-pyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

Traditional Name

(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-2,16-dimethyl-15-[(1S)-1-[(2R)-4-methyl-6-oxo-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC([H])([H])C2=C(C([H])([H])[H])C([H])([H])[C@@]([H])(OC2=O)[C@@]([H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]3([H])[C@]4([H])C([H])([H])[C@@]5([H])O[C@]55[C@@]([H])(O[H])C([H])=C([H])C(=O)[C@]5(C([H])([H])[H])[C@@]4([H])C([H])([H])C([H])([H])[C@]23C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C34H48O11/c1-15-11-22(43-30(41)18(15)14-42-31-29(40)28(39)27(38)23(13-35)44-31)16(2)19-5-6-20-17-12-26-34(45-26)25(37)8-7-24(36)33(34,4)21(17)9-10-32(19,20)3/h7-8,16-17,19-23,25-29,31,35,37-40H,5-6,9-14H2,1-4H3/t16-,17-,19+,20-,21-,22+,23+,25-,26+,27+,28-,29+,31+,32+,33-,34+/m0/s1

InChI Key

WKCJIGSUKSPCKI-WNXUODGFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Physalis longifolia	JEOL database	Zhang, H., et al, J. Nat. Prod. 74, 2532 (2011)
Withania somnifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
Steroidal glycoside
5,6-epoxysteroid
Glycosyl compound
O-glycosyl compound
Dihydropyranone
Cyclohexenone
Oxepane
Monosaccharide
Oxane
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Polyol
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Acetal
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:69119 )
epoxide (CHEBI:69119 )
beta-D-glucoside (CHEBI:69119 )
monosaccharide derivative (CHEBI:69119 )
enone (CHEBI:69119 )
delta-lactone (CHEBI:69119 )
4-hydroxy steroid (CHEBI:69119 )
ergostanoid (CHEBI:69119 )
withanolide saponin (CHEBI:69119 )

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	0.84	ALOGPS
logP	1.81	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	175.51 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	159.61 m³·mol⁻¹	ChemAxon
Polarizability	66.63 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	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

164705

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

69119

Good Scents ID

Not Available

References

General References

Jayaprakasam B, Zhang Y, Seeram NP, Nair MG: Growth inhibition of human tumor cell lines by withanolides from Withania somnifera leaves. Life Sci. 2003 Nov 21;74(1):125-32. doi: 10.1016/j.lfs.2003.07.007. [PubMed:14575818 ]
Zhang, H., et al. (2011). Zhang, H., et al, J. Nat. Prod. 74, 2532 (2011). J. Nat. Prod..

Showing NP-Card for sitoindoside IX (NP0036400)

MOL for NP0036400 (sitoindoside IX)

3D MOL for NP0036400 (sitoindoside IX)

3D SDF for NP0036400 (sitoindoside IX)

3D-SDF for NP0036400 (sitoindoside IX)

PDB for NP0036400 (sitoindoside IX)

3D PDB for NP0036400 (sitoindoside IX)

SMILES for NP0036400 (sitoindoside IX)

INCHI for NP0036400 (sitoindoside IX)

Structure for NP0036400 (sitoindoside IX)

3D Structure for NP0036400 (sitoindoside IX)