NP-MRD: Showing NP-Card for Prototribestin (NP0073686)

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Record Information

Version

2.0

Created at

2022-04-28 18:54:41 UTC

Updated at

2022-04-28 18:54:41 UTC

NP-MRD ID

NP0073686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prototribestin

Description

[(2R,3S,4S,5R,6R)-4-hydroxy-6-{[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icos-18-en-16-yl]oxy}-2-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxidanesulfonic acid 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. Prototribestin is found in Tribulus terrestris . Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6R)-4-hydroxy-6-{[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icos-18-en-16-yl]oxy}-2-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxidanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220542D          

 67 74  0  0  1  0            999 V2000
    8.1476    0.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4789    1.1708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9902    1.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1703    1.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6816    2.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8616    2.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5303    1.5629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0190    0.8982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8390    0.9891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3276    0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5077    0.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877    0.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8677    0.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    0.7165    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7103    1.4721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0941    2.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820    1.6041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5581    0.7981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8459    0.3816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2297    0.9302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5610    1.6857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411    1.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8370    0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0484    0.8529    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5558    0.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444    0.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9485   -0.0285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7371    0.2137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3413   -0.3481    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1568   -1.1522    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3681   -1.3945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640   -0.8326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9754   -1.0749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836   -2.1986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7609   -1.7141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1299   -0.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7340   -0.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1361    1.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6140    0.3811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9706   -0.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2989    1.2617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7876    0.5970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4563   -0.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9450   -0.8233    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7649   -0.7324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0962    0.0231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6076    0.6878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9389    1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7589    1.5342    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0902    2.2898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9101    2.3806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3988    1.7160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0675    0.9604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2475    0.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5562    0.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2188    1.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2414    3.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6015    2.9545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9162    0.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2536   -1.3971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0736   -1.3063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9827   -0.4863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1645   -2.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8936   -1.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6136   -1.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1023   -2.2435    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  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  1  0  0  0
 20 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  6  0  0  0
 31 34  1  1  0  0  0
 30 35  1  6  0  0  0
 29 36  1  1  0  0  0
 36 37  1  0  0  0  0
 24 38  1  6  0  0  0
 20 39  1  6  0  0  0
 19 40  1  6  0  0  0
 14 41  1  1  0  0  0
  2 42  1  1  0  0  0
 43 42  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 43 48  1  0  0  0  0
 48 49  1  6  0  0  0
 50 49  1  1  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 50 55  1  0  0  0  0
 54 56  1  6  0  0  0
 53 57  1  1  0  0  0
 52 58  1  6  0  0  0
 51 59  1  6  0  0  0
 47 60  1  6  0  0  0
 46 61  1  6  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 62 64  2  0  0  0  0
 62 65  1  0  0  0  0
 45 66  1  1  0  0  0
 66 67  1  0  0  0  0
M  END

     RDKit          3D

141148  0  0  0  0  0  0  0  0999 V2000
   -7.8195   -2.0723    2.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5475   -2.7555    0.8506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1390   -1.8357   -0.1128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1824   -0.9816   -0.4797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7221   -0.0331   -1.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9085    1.2645   -0.9384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9561    2.0188   -1.7475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6455    2.0218   -3.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0182    3.4321   -1.2751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1290    4.2994   -2.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5102    5.2148   -2.3536 S   0  0  1  0  0  6  0  0  0  0  0  0
  -10.1682    6.5828   -1.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1024    5.4647   -3.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6376    4.5060   -1.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9074    3.8832   -0.3840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3583    3.9918    1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4295    4.7770    1.7985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6963    3.3042   -0.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6323    2.0105   -1.0052 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5345    1.3229   -0.5003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5502    1.0767   -1.4501 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3015    1.9252   -1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802    1.5355    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732    0.1303    0.3160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8255   -0.4373    1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9948   -0.7473   -0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4917   -1.9583   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3727   -2.4821   -0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5032   -1.4133    0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8976   -1.6365    0.2011 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6148   -2.7908    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0403   -2.5434    0.3717 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9827   -2.6562    1.3712 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5589   -2.5367   -0.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9850   -1.6865    2.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2628   -0.9892    1.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3764   -1.3983    1.1262 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9064   -2.7937    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3406   -0.9432   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.2490    2.8497   -2.9113 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0853    1.2800   -0.6331 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6775    1.5950    0.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9329   -0.2206   -0.8516 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6176   -0.4008   -2.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7392   -0.6877   -0.0227 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9899   -0.4717    1.3392 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3807   -0.5487    0.5094 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0837    0.1807   -0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985   -1.0744   -0.0504 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8551   -0.5110    0.5967 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0279   -0.3883    2.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    0.7514   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1082   -0.3266   -1.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1975   -1.8439   -1.1879 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.1040   -1.1290   -1.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.5530   -2.0217    0.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8003   -2.8807    2.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.3699    1.1861    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282220542D          

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M  END
> <DATABASE_ID>
NP0073686

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C45H74O21S/c1-19(18-59-40-35(52)34(51)32(49)28(16-46)62-40)8-13-45(55)20(2)30-27(65-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)61-42-39(64-41-36(53)33(50)31(48)21(3)60-41)37(54)38(29(17-47)63-42)66-67(56,57)58/h6,19-21,23-42,46-55H,7-18H2,1-5H3,(H,56,57,58)/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33-,34+,35-,36-,37-,38-,39-,40-,41+,42-,43+,44+,45-/m1/s1

> <INCHI_KEY>
AWNPFXCAAKPCBE-YGXMXTOKSA-N

> <FORMULA>
C45H74O21S

> <MOLECULAR_WEIGHT>
983.13

> <EXACT_MASS>
982.444330577

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
141

> <JCHEM_AVERAGE_POLARIZABILITY>
101.50219163929258

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-4-hydroxy-6-{[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-en-16-yl]oxy}-2-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.37

> <JCHEM_LOGP>
-2.194413900721769

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.569840055760793

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.858536945646299

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483772987566265

> <JCHEM_POLAR_SURFACE_AREA>
330.50999999999993

> <JCHEM_REFRACTIVITY>
229.4640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-4-hydroxy-6-{[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-en-16-yl]oxy}-2-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      15.209   0.775   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.827   2.185   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.915   3.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.384   3.257   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.472   4.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.942   4.328   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.323   2.917   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.235   1.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.766   1.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.678   0.606   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.148   0.436   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.617   0.266   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.086   0.097   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.174   1.337   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.793   2.748   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.642   3.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.313   2.994   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.642   1.490   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.312   0.712   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.162   1.736   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.781   3.147   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.690   2.189   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.562   1.140   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.090   1.592   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.037   0.543   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.510   0.995   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.637  -0.053   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.109   0.399   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.237  -0.650   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.893  -2.151   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.421  -2.603   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.293  -1.554   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.821  -2.007   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.076  -4.104   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -7.020  -3.200   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.709  -0.198   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -8.837  -1.246   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.254   3.093   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.013   0.711   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.160  -0.820   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.412  -0.001   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      17.358   2.355   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      18.270   1.114   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      17.652  -0.296   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      18.564  -1.537   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      20.095  -1.367   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      20.713   0.043   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      19.801   1.284   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      20.419   2.694   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      21.950   2.864   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      22.568   4.274   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      24.099   4.444   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      25.011   3.203   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      24.393   1.793   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      22.862   1.623   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      25.305   0.552   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      26.542   3.373   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      24.717   5.854   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      21.656   5.515   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      22.244   0.213   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      21.007  -2.608   0.000  0.00  0.00           O+0
HETATM   62  S   UNK     0      22.537  -2.438   0.000  0.00  0.00           S+0
HETATM   63  O   UNK     0      22.368  -0.908   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      22.707  -3.969   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      24.068  -2.269   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      17.945  -2.947   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      18.858  -4.188   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18   41                                             
CONECT   15   14    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   14   19                                                  
CONECT   19   18   20   40                                                  
CONECT   20   19   21   22   39                                             
CONECT   21   20   17                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   38                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
CONECT   34   31                                                            
CONECT   35   30                                                            
CONECT   36   29   37                                                       
CONECT   37   36                                                            
CONECT   38   24                                                            
CONECT   39   20                                                            
CONECT   40   19                                                            
CONECT   41   14                                                            
CONECT   42    2   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   66                                                  
CONECT   46   45   47   61                                                  
CONECT   47   46   48   60                                                  
CONECT   48   47   43   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   55                                                  
CONECT   51   50   52   59                                                  
CONECT   52   51   53   58                                                  
CONECT   53   52   54   57                                                  
CONECT   54   53   55   56                                                  
CONECT   55   54   50                                                       
CONECT   56   54                                                            
CONECT   57   53                                                            
CONECT   58   52                                                            
CONECT   59   51                                                            
CONECT   60   47                                                            
CONECT   61   46   62                                                       
CONECT   62   61   63   64   65                                             
CONECT   63   62                                                            
CONECT   64   62                                                            
CONECT   65   62                                                            
CONECT   66   45   67                                                       
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  148    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6R)-4-Hydroxy-6-{[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]-5-oxapentacyclo[10.8.0.0,.0,.0,]icos-18-en-16-yl]oxy}-2-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxidanesulfonate	Generator
[(2R,3S,4S,5R,6R)-4-Hydroxy-6-{[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]-5-oxapentacyclo[10.8.0.0,.0,.0,]icos-18-en-16-yl]oxy}-2-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxidanesulphonate	Generator
[(2R,3S,4S,5R,6R)-4-Hydroxy-6-{[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl]-5-oxapentacyclo[10.8.0.0,.0,.0,]icos-18-en-16-yl]oxy}-2-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxidanesulphonic acid	Generator

Chemical Formula

C₄₅H₇₄O₂₁S

Average Mass

983.1300 Da

Monoisotopic Mass

982.44433 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C45H74O21S/c1-19(18-59-40-35(52)34(51)32(49)28(16-46)62-40)8-13-45(55)20(2)30-27(65-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)61-42-39(64-41-36(53)33(50)31(48)21(3)60-41)37(54)38(29(17-47)63-42)66-67(56,57)58/h6,19-21,23-42,46-55H,7-18H2,1-5H3,(H,56,57,58)/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33-,34+,35-,36-,37-,38-,39-,40-,41+,42-,43+,44+,45-/m1/s1

InChI Key

AWNPFXCAAKPCBE-YGXMXTOKSA-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
Tribulus terrestris	Plant	KNApSAcK

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
Furostane-skeleton
Diterpene glycoside
22-hydroxysteroid
Diterpenoid
Hydroxysteroid
Terpene glycoside
Delta-5-steroid
Disaccharide sulfate
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Fatty acyl
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Oxane
Tetrahydrofuran
Organic sulfuric acid or derivatives
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.37	ALOGPS
logP	-2.2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	330.51 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	229.46 m³·mol⁻¹	ChemAxon
Polarizability	101.5 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154497289

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Prototribestin (NP0073686)

MOL for NP0073686 (Prototribestin)

3D MOL for NP0073686 (Prototribestin)

3D SDF for NP0073686 (Prototribestin)

3D-SDF for NP0073686 (Prototribestin)

PDB for NP0073686 (Prototribestin)

3D PDB for NP0073686 (Prototribestin)

SMILES for NP0073686 (Prototribestin)

INCHI for NP0073686 (Prototribestin)

Structure for NP0073686 (Prototribestin)

3D Structure for NP0073686 (Prototribestin)