NP-MRD: Showing NP-Card for Khasianine (NP0044565)

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Record Information

Version

1.0

Created at

2022-02-24 21:02:27 UTC

Updated at

2022-02-24 21:02:27 UTC

NP-MRD ID

NP0044565

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Khasianine

Description

Khasianine 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. Khasianine is found in Solanum aethiopicum, Solanum myriacanthum, Solanum nigrum and Solanum virginianum. It was first documented in 1994 (PMID: 8064291). Based on a literature review a significant number of articles have been published on Khasianine (PMID: 29306798) (PMID: 35183690) (PMID: 32552210) (PMID: 30723741).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302242222022D          

 56 63  0  0  1  0            999 V2000
    5.6817    1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5574    0.8587    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1441    0.2787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7738   -0.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9582   -0.3342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8245    0.4799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0089    0.6043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4542    1.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -0.1330    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2253   -0.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150   -0.1809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3617    0.5084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7320    1.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5556    1.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9084    1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3442   -0.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9327    0.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3861    1.0059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2097    0.9580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6630    1.6473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4866    1.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399    2.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2927    2.3845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7460    3.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757    3.8110    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8291    4.5003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6527    4.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4588    5.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9121    5.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1819    4.5962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3582    4.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    3.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691    2.4324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.1922    1.7911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1853    0.5563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0920   -1.1482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4353    1.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4811   -0.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6670   -0.3594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 30 39  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 23 42  1  0  0  0  0
 42 43  1  1  0  0  0
 21 44  1  0  0  0  0
 44 45  1  0  0  0  0
 15 45  1  0  0  0  0
 12 46  1  6  0  0  0
 11 47  1  1  0  0  0
  9 48  1  6  0  0  0
  6 49  1  6  0  0  0
  5 50  1  6  0  0  0
  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  1  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
  3 56  1  0  0  0  0
M  END

     RDKit          3D

114121  0  0  0  0  0  0  0  0999 V2000
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    4.2582    1.6009   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198   -1.1712   -2.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0273   -0.7984   -2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7536    1.0058   -3.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6011    0.9854    2.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5057   -2.1126    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5459    0.5206   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7476   -1.9964   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
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 23 22  1  0
 22 21  1  0
 21 20  1  0
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 39101  1  0
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 50113  1  1
 51114  1  0
 48111  1  1
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 46109  1  1
 47110  1  0
 44107  1  6
 45108  1  0
 42105  1  6
 43106  1  0
M  END


  Mrv1652302242222022D          

 56 63  0  0  1  0            999 V2000
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    5.7738   -0.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9582   -0.3342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8245    0.4799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0089    0.6043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4542    1.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -0.1330    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.8150   -0.1809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7320    1.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5556    1.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9084    1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1678   -0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3442   -0.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091    0.3646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9327    0.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3861    1.0059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2097    0.9580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4866    1.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9399    2.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2927    2.3845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7460    3.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757    3.8110    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8291    4.5003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6527    4.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4588    5.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9121    5.9268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352    5.2855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2649    6.0227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819    4.5962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3582    4.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    3.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691    2.4324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0988    3.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0158    1.7431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1922    1.7911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611    1.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0848    1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1853    0.5563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914   -0.2289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3474   -0.9049    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617    0.1096    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0920   -1.1482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4353    1.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2494    1.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7723    0.5463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5863    0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4811   -0.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6670   -0.3594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 30 39  1  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 23 42  1  0  0  0  0
 42 43  1  1  0  0  0
 21 44  1  0  0  0  0
 44 45  1  0  0  0  0
 15 45  1  0  0  0  0
 12 46  1  6  0  0  0
 11 47  1  1  0  0  0
  9 48  1  6  0  0  0
  6 49  1  6  0  0  0
  5 50  1  6  0  0  0
  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  1  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
  3 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044565

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CN1)O2)O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C39H63NO11/c1-18-8-13-39(40-16-18)19(2)28-26(51-39)15-25-23-7-6-21-14-22(9-11-37(21,4)24(23)10-12-38(25,28)5)48-36-33(46)31(44)34(27(17-41)49-36)50-35-32(45)30(43)29(42)20(3)47-35/h6,18-20,22-36,40-46H,7-17H2,1-5H3/t18-,19+,20+,22+,23-,24+,25+,26+,27-,28+,29+,30-,31-,32-,33-,34-,35+,36-,37+,38+,39-/m1/s1

> <INCHI_KEY>
KRQDMAXNTWLTDZ-HCTICQNOSA-N

> <FORMULA>
C39H63NO11

> <MOLECULAR_WEIGHT>
721.929

> <EXACT_MASS>
721.440111853

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
114

> <JCHEM_AVERAGE_POLARIZABILITY>
81.13365983675587

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-eneoxy]oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.115116222666665

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.499485811342254

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.948316831019683

> <JCHEM_PKA_STRONGEST_BASIC>
9.539943811828564

> <JCHEM_POLAR_SURFACE_AREA>
179.56

> <JCHEM_REFRACTIVITY>
185.22970000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-eneoxy]oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-22         0                                  
HETATM    1  C   UNK     0      10.606   3.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.374   1.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.469   0.520   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.778  -0.856   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.255  -0.624   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.006   0.896   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.483   1.128   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.315   2.424   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.792  -0.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.887  -1.331   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.255  -0.338   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.408   0.949   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.100   2.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.637   2.415   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.871   0.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.562   2.236   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.180  -0.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.026  -1.803   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.563  -1.714   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.642  -0.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.204   0.681   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.741   0.591   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.587   1.878   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.125   1.788   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.971   3.075   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.508   2.985   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.355   4.272   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.280   4.451   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.126   5.738   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.435   7.114   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.281   8.401   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.818   8.311   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.590   9.777   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.436  11.063   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.052   9.866   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.361  11.242   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.206   8.580   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.669   8.669   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.897   7.203   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.742   4.541   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -2.051   5.917   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.896   3.254   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -0.359   3.343   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       0.487   2.057   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.025   2.146   0.000  0.00  0.00           C+0
HETATM   46  H   UNK     0       5.946   1.038   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.717  -0.427   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.249  -1.689   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      10.382   0.205   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       9.505  -2.143   0.000  0.00  0.00           H+0
HETATM   51  C   UNK     0      12.013   1.961   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      13.532   2.211   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      14.508   1.020   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      16.028   1.269   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      13.965  -0.421   0.000  0.00  0.00           C+0
HETATM   56  N   UNK     0      12.445  -0.671   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   51   56                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   10   50                                             
CONECT    6    5    2    7   49                                             
CONECT    7    6    8    9   14                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   48                                             
CONECT   10    9    5                                                       
CONECT   11    9   12   19   47                                             
CONECT   12   11   13   15   46                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   17   45                                             
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   11                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22   44                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   42                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   40                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   39                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   30                                                       
CONECT   40   28   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   23   43                                                  
CONECT   43   42                                                            
CONECT   44   21   45                                                       
CONECT   45   44   15                                                       
CONECT   46   12                                                            
CONECT   47   11                                                            
CONECT   48    9                                                            
CONECT   49    6                                                            
CONECT   50    5                                                            
CONECT   51    3   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55    3                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  126    0
END

View in JSmol

Synonyms

Value	Source
L-Rhamnopyranosyl-14-D-glucopyranose solasodine	MeSH

Chemical Formula

C₃₉H₆₃NO₁₁

Average Mass

721.9290 Da

Monoisotopic Mass

721.44011 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-eneoxy]oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CN1)O2)O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C39H63NO11/c1-18-8-13-39(40-16-18)19(2)28-26(51-39)15-25-23-7-6-21-14-22(9-11-37(21,4)24(23)10-12-38(25,28)5)48-36-33(46)31(44)34(27(17-41)49-36)50-35-32(45)30(43)29(42)20(3)47-35/h6,18-20,22-36,40-46H,7-17H2,1-5H3/t18-,19+,20+,22+,23-,24+,25+,26+,27-,28+,29+,30-,31-,32-,33-,34-,35+,36-,37+,38+,39-/m1/s1

InChI Key

KRQDMAXNTWLTDZ-HCTICQNOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Solanum aethiopicum	LOTUS Database	35616633
Solanum myriacanthum	LOTUS Database	35616633
Solanum nigrum	LOTUS Database	35616633
Solanum platanifolium	Linington's dataset npmrd_submissions_20220207	8064291
Solanum virginianum	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
Diterpene glycoside
Spirosolane skeleton
Diterpenoid
Steroidal alkaloid
Azasteroid
Delta-5-steroid
Terpene glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Azaspirodecane
Alkaloid or derivatives
Oxane
Piperidine
Oxolane
Secondary alcohol
Hemiaminal
Polyol
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Primary alcohol
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	2.07	ALOGPS
logP	2.12	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.95	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	179.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	185.23 m³·mol⁻¹	ChemAxon
Polarizability	81.13 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	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

10181215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21573759

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Puri R, Wong TC, Puri RK: 1H- and 13C-nmr assignments and structural determination of a novel glycoalkaloid from Solanum platanifolium. J Nat Prod. 1994 May;57(5):587-96. doi: 10.1021/np50107a004. [PubMed:8064291 ]
Gu XY, Shen XF, Wang L, Wu ZW, Li F, Chen B, Zhang GL, Wang MK: Bioactive steroidal alkaloids from the fruits of Solanum nigrum. Phytochemistry. 2018 Mar;147:125-131. doi: 10.1016/j.phytochem.2017.12.020. Epub 2018 Jan 5. [PubMed:29306798 ]
Yang Y, Zhang Y, Chen X, Su Z, Deng Y, Zhao Q: Khasianine ameliorates psoriasis-like skin inflammation and represses TNF-alpha/NF-kappaB axis mediated transactivation of IL-17A and IL-33 in keratinocytes. J Ethnopharmacol. 2022 Feb 17:115124. doi: 10.1016/j.jep.2022.115124. [PubMed:35183690 ]
Ono M, Shimode M, Tsutsumi S, Yasuda S, Okawa M, Kinjo J, Miyashita H, Ikeda T, Yoshimitsu H, Nohara T: A new steroidal glycoside from the fruits of Solanum myriacanthum. Nat Prod Res. 2022 Jan;36(1):326-333. doi: 10.1080/14786419.2020.1781117. Epub 2020 Jun 19. [PubMed:32552210 ]
Chen F, Shen X, Huang P, Fu H, Jin Y, Wen C: Quantification of Lappaconitine in Mouse Blood by UPLC-MS/MS and Its Application to a Pharmacokinetic Study. Biomed Res Int. 2019 Jan 6;2019:6262105. doi: 10.1155/2019/6262105. eCollection 2019. [PubMed:30723741 ]

Showing NP-Card for Khasianine (NP0044565)

MOL for NP0044565 (Khasianine)

3D MOL for NP0044565 (Khasianine)

3D SDF for NP0044565 (Khasianine)

3D-SDF for NP0044565 (Khasianine)

PDB for NP0044565 (Khasianine)

3D PDB for NP0044565 (Khasianine)

SMILES for NP0044565 (Khasianine)

INCHI for NP0044565 (Khasianine)

Structure for NP0044565 (Khasianine)

3D Structure for NP0044565 (Khasianine)