NP-MRD: Showing NP-Card for (-)-Tieghemelin (NP0080916)

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Record Information

Version

2.0

Created at

2022-04-29 01:53:29 UTC

Updated at

2022-04-29 01:53:29 UTC

NP-MRD ID

NP0080916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Tieghemelin

Description

(2S,3S,4S,5R,6R)-6-{[(2S,3R,4R,4aR,5R,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-({[(2S,3R,4R,5R)-3-{[(2S,3R,4R,5R,6S)-5-{[(2S,3R,4S,5R)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,5,8-trihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (-)-Tieghemelin is found in Tieghemella heckelii. Based on a literature review very few articles have been published on (2S,3S,4S,5R,6R)-6-{[(2S,3R,4R,4aR,5R,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-({[(2S,3R,4R,5R)-3-{[(2S,3R,4R,5R,6S)-5-{[(2S,3R,4S,5R)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,5,8-trihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203532D          

 87 96  0  0  1  0            999 V2000
    8.5520   -1.7309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9645   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5520   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7270   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -1.7309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7766    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8342    2.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7605    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3480    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2355    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8230    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9980    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5855    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4730    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0605    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2980    3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7105    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2980    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5355    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9480    3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5355    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9480    5.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7730    5.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1855    4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7730    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1855    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0105    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1855    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5355    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7105    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    2.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -2.4454    0.0000 O   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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 23 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
 32 27  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  0  0  0  0
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 31 39  1  1  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
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M  END

     RDKit          3D

179188  0  0  0  0  0  0  0  0999 V2000
   14.7031   -2.3806    1.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0016   -0.9622    1.5046 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9104   -0.1340    1.5272 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9486   -0.4574    0.5733 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0309    0.6052    0.5542 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7842    0.2587    1.0109 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5420    1.0858    2.2794 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4903    0.8129    3.2445 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1780    0.6748    2.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1978    0.9357    1.8522 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3734    0.1678    0.6993 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7672    1.1798   -1.9624 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2613    2.0095   -0.8110 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9623    1.6419   -0.3777 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    1.1834    0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2880   -1.1603    2.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -2.0117    1.4819 C   0  0  1  0  0  0  0  0  0  0  0  0
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  -11.9000   -2.1770   -0.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4210   -2.5847   -1.2611 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.8924   -3.9575   -1.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2130   -4.5719   -2.5881 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0313   -4.6118   -0.6639 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292203532D          

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   -8.7730    5.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1855    4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7730    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1855    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0105    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1855    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5355    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7105    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5855    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    2.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0080916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@H]2[C@H](O)CO[C@@H](O[C@H]3[C@H](C)O[C@@H](O[C@@H]4[C@H](O)[C@H](O)CO[C@H]4OC(=O)[C@]45CCC(C)(C)C[C@H]4C4=CC[C@@H]6[C@@]7(C)C[C@H](O)[C@H](O[C@@H]8O[C@@H]([C@@H](O)[C@H](O)[C@H]8O)C(O)=O)[C@@](C)(CO)[C@@H]7[C@H](O)C[C@@]6(C)[C@]4(C)C[C@H]5O)[C@H](O)[C@H]3O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C58H92O29/c1-20-30(65)32(67)36(71)48(80-20)83-41-27(63)18-78-47(39(41)74)82-40-21(2)81-49(38(73)35(40)70)85-43-31(66)26(62)17-79-51(43)87-52(77)58-12-11-53(3,4)13-23(58)22-9-10-28-54(5)14-25(61)45(86-50-37(72)33(68)34(69)42(84-50)46(75)76)55(6,19-59)44(54)24(60)15-57(28,8)56(22,7)16-29(58)64/h9,20-21,23-45,47-51,59-74H,10-19H2,1-8H3,(H,75,76)/t20-,21-,23-,24+,25-,26+,27+,28+,29+,30-,31+,32+,33-,34-,35+,36+,37+,38+,39+,40-,41-,42-,43+,44+,45-,47-,48-,49-,50-,51-,54+,55-,56+,57+,58+/m0/s1

> <INCHI_KEY>
QXLGWIOGISQPDB-WPVRHFAJSA-N

> <FORMULA>
C58H92O29

> <MOLECULAR_WEIGHT>
1253.345

> <EXACT_MASS>
1252.572426942

> <JCHEM_ACCEPTOR_COUNT>
28

> <JCHEM_ATOM_COUNT>
179

> <JCHEM_AVERAGE_POLARIZABILITY>
127.73862544003511

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
17

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(2S,3R,4R,4aR,5R,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-({[(2S,3R,4R,5R)-3-{[(2S,3R,4R,5R,6S)-5-{[(2S,3R,4S,5R)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,5,8-trihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-3.977063515

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.726653231012758

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.346000232015142

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686500772733236

> <JCHEM_POLAR_SURFACE_AREA>
470.35000000000014

> <JCHEM_REFRACTIVITY>
286.80809999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(2S,3R,4R,4aR,5R,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-({[(2S,3R,4R,5R)-3-{[(2S,3R,4R,5R,6S)-5-{[(2S,3R,4S,5R)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,5,8-trihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      15.964  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.734  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.964  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.424  -0.564   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.654  -1.897   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.424  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.654  -4.565   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.114  -4.565   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      14.424  -5.898   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.114  -1.897   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.650   2.920   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.397   3.643   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.757   4.366   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.510  -2.103   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.742  -1.380   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.976   4.771   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -0.206   6.105   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.976   7.438   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.516   7.438   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.286   6.105   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -3.286   3.437   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -4.826   3.437   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -5.596   4.771   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -7.136   4.771   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -7.906   3.437   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -7.136   2.104   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -5.596   2.104   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -4.826   0.770   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -7.906   0.770   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -9.446   3.437   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0     -10.216   4.771   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -9.446   6.105   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0     -10.216   7.438   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -11.756   7.438   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -12.526   6.105   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -11.756   4.771   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0     -12.526   3.437   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0     -14.066   6.105   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0     -14.836   7.438   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0     -14.066   8.772   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0     -14.836  10.106   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0     -16.376  10.106   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0     -17.146   8.772   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0     -16.376   7.438   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0     -17.146   6.105   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0     -18.686   8.772   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0     -17.146  11.439   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0     -14.066  11.439   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0     -12.526   8.772   0.000  0.00  0.00           O+0
HETATM   77  C   UNK     0      -7.906   6.105   0.000  0.00  0.00           C+0
HETATM   78  O   UNK     0      -4.826   6.105   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      -3.286   8.772   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0       3.035   4.969   0.000  0.00  0.00           O+0
HETATM   81  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0       6.885   3.635   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0      16.734   0.770   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0      18.274  -1.897   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0      16.734  -4.565   0.000  0.00  0.00           O+0
CONECT    1    2    6   87                                                  
CONECT    2    1    3   86                                                  
CONECT    3    2    4   85                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   24   84                                             
CONECT   16   15   17   21                                                  
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   16   22   83                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28   82                                             
CONECT   24   23   15   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   23   29   81                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   80                                                  
CONECT   31   30   32   36   39                                             
CONECT   32   31   27   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   37   38                                             
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34                                                            
CONECT   38   34                                                            
CONECT   39   31   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   47                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   79                                                  
CONECT   46   45   47   78                                                  
CONECT   47   46   42   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   54                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   77                                                  
CONECT   52   51   53   57                                                  
CONECT   53   52   54   56                                                  
CONECT   54   53   49   55                                                  
CONECT   55   54                                                            
CONECT   56   53                                                            
CONECT   57   52   58                                                       
CONECT   58   57   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   76                                                  
CONECT   62   61   63   65                                                  
CONECT   63   62   58   64                                                  
CONECT   64   63                                                            
CONECT   65   62   66                                                       
CONECT   66   65   67   71                                                  
CONECT   67   66   68                                                       
CONECT   68   67   69   75                                                  
CONECT   69   68   70   74                                                  
CONECT   70   69   71   73                                                  
CONECT   71   70   66   72                                                  
CONECT   72   71                                                            
CONECT   73   70                                                            
CONECT   74   69                                                            
CONECT   75   68                                                            
CONECT   76   61                                                            
CONECT   77   51                                                            
CONECT   78   46                                                            
CONECT   79   45                                                            
CONECT   80   30                                                            
CONECT   81   28                                                            
CONECT   82   23                                                            
CONECT   83   21                                                            
CONECT   84   15                                                            
CONECT   85    3                                                            
CONECT   86    2                                                            
CONECT   87    1                                                            
MASTER        0    0    0    0    0    0    0    0   87    0  192    0
END

View in JSmol

Synonyms

Value

Source

(2S,3S,4S,5R,6R)-6-{[(2S,3R,4R,4ar,5R,6ar,6BS,8R,8ar,12as,14ar,14BR)-8a-({[(2S,3R,4R,5R)-3-{[(2S,3R,4R,5R,6S)-5-{[(2S,3R,4S,5R)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,5,8-trihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

Generator

Chemical Formula

C₅₈H₉₂O₂₉

Average Mass

1253.3450 Da

Monoisotopic Mass

1252.57243 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@H]2[C@H](O)CO[C@@H](O[C@H]3[C@H](C)O[C@@H](O[C@@H]4[C@H](O)[C@H](O)CO[C@H]4OC(=O)[C@]45CCC(C)(C)C[C@H]4C4=CC[C@@H]6[C@@]7(C)C[C@H](O)[C@H](O[C@@H]8O[C@@H]([C@@H](O)[C@H](O)[C@H]8O)C(O)=O)[C@@](C)(CO)[C@@H]7[C@H](O)C[C@@]6(C)[C@]4(C)C[C@H]5O)[C@H](O)[C@H]3O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C58H92O29/c1-20-30(65)32(67)36(71)48(80-20)83-41-27(63)18-78-47(39(41)74)82-40-21(2)81-49(38(73)35(40)70)85-43-31(66)26(62)17-79-51(43)87-52(77)58-12-11-53(3,4)13-23(58)22-9-10-28-54(5)14-25(61)45(86-50-37(72)33(68)34(69)42(84-50)46(75)76)55(6,19-59)44(54)24(60)15-57(28,8)56(22,7)16-29(58)64/h9,20-21,23-45,47-51,59-74H,10-19H2,1-8H3,(H,75,76)/t20-,21-,23-,24+,25-,26+,27+,28+,29+,30-,31+,32+,33-,34-,35+,36+,37+,38+,39+,40-,41-,42-,43+,44+,45-,47-,48-,49-,50-,51-,54+,55-,56+,57+,58+/m0/s1

InChI Key

QXLGWIOGISQPDB-WPVRHFAJSA-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
Tieghemella heckelii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Oligosaccharide
12-alpha-hydroxysteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
Hydroxysteroid
12-hydroxysteroid
Steroid
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	-0.61	ALOGPS
logP	-4	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	28	ChemAxon
Hydrogen Donor Count	17	ChemAxon
Polar Surface Area	470.35 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	286.81 m³·mol⁻¹	ChemAxon
Polarizability	127.74 Å³	ChemAxon
Number of Rings	10	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

162950677

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Tieghemelin (NP0080916)

MOL for NP0080916 ((-)-Tieghemelin)

3D MOL for NP0080916 ((-)-Tieghemelin)

3D SDF for NP0080916 ((-)-Tieghemelin)

3D-SDF for NP0080916 ((-)-Tieghemelin)

PDB for NP0080916 ((-)-Tieghemelin)

3D PDB for NP0080916 ((-)-Tieghemelin)

SMILES for NP0080916 ((-)-Tieghemelin)

INCHI for NP0080916 ((-)-Tieghemelin)

Structure for NP0080916 ((-)-Tieghemelin)

3D Structure for NP0080916 ((-)-Tieghemelin)