holothurin B

ID: ALA248359

PubChem CID: 44440861

Max Phase: Preclinical

Molecular Formula: C41H63NaO17S

Molecular Weight: 861.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3CC[C@]4(C)C5=C[C@H](O)C67C(=O)O[C@@](C)(C8CCC(C)(C)O8)[C@@]6(O)CC[C@@]7(C)[C@@H]5CCC4C3(C)C)OC[C@@H](OS(=O)(=O)[O-])[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.[Na+]

Standard InChI:  InChI=1S/C41H64O17S.Na/c1-19-27(43)29(45)30(46)32(53-19)55-31-28(44)22(58-59(49,50)51)18-52-33(31)54-25-12-14-37(6)21-17-24(42)41-34(47)57-39(8,26-11-13-35(2,3)56-26)40(41,48)16-15-38(41,7)20(21)9-10-23(37)36(25,4)5;/h17,19-20,22-33,42-46,48H,9-16,18H2,1-8H3,(H,49,50,51);/q;+1/p-1/t19-,20-,22-,23?,24+,25+,26?,27-,28+,29+,30-,31-,32+,33+,37-,38+,39+,40+,41?;/m1./s1

Standard InChI Key:  XPKZSKANINADOD-DZMFXSCCSA-M

Molfile:  

     RDKit          2D

 63 69  0  0  0  0  0  0  0  0999 V2000
   -2.1678   -3.7685    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -0.3430   -5.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430   -6.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3699   -7.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3699   -5.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874   -5.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -6.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8020   -7.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -6.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793   -4.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -7.0524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476   -7.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7730   -7.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7998   -5.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7989   -4.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333   -5.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187   -5.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5120   -4.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2411   -4.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0300   -4.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0402   -3.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2575   -3.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638   -3.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770   -3.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2243   -6.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8296   -3.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8234   -2.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7689   -6.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7704   -5.8165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4792   -5.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1946   -5.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1966   -6.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4832   -7.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4850   -7.8766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -5.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -7.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143   -5.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -4.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1988   -8.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081   -7.8752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6197   -8.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256   -9.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138   -9.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1958   -9.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835   -9.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3410   -9.5127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3302   -7.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183  -10.3439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891   -6.0554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4925   -8.6942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9029   -4.5756    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104   -3.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -4.5734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7261   -4.5799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4722   -3.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1559   -3.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9387   -2.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -2.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7322   -2.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5584   -4.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182   -5.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7213   -6.0277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 62  1  0
 29 11  1  0
 29 30  1  0
  2  3  1  0
  2  5  1  0
 14 16  2  0
 29 34  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 62 17  1  0
 34 35  1  6
 20 15  1  0
 32 36  1  6
 15 16  1  0
 33 37  1  1
 20 17  1  0
 21 38  1  6
  6 14  1  0
 15 39  1  6
  7  8  1  0
 35 40  1  0
 40 41  1  0
  8  9  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 20 21  1  0
 40 45  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
  9 62  1  0
 45 46  1  6
  3  4  1  0
 43 47  1  6
  6 10  1  1
 42 48  1  1
  4  7  1  0
 44 49  1  1
  3 11  1  1
 29 50  1  6
 21 22  1  0
 40 51  1  6
 22 23  1  0
 36 52  1  0
 23 24  1  0
 52 53  1  0
 20 24  1  0
 52 54  2  0
  6  5  1  0
 52 55  2  0
 27 56  1  0
 24 25  2  0
  4 12  1  0
 17 26  1  6
  6  7  1  0
 56 57  1  0
 57 58  1  0
 58 59  1  0
 59 27  1  0
 22 27  1  0
 57 60  1  0
  4 13  1  0
 57 61  1  0
 22 28  1  6
 62 63  1  1
M  CHG  2   1   1  53  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 861.01

Molecular Weight (Monoisotopic): 860.3864

AlogP: 1.43

#Rotatable Bonds: 7

Polar Surface Area: 257.43

Molecular Species: ACID

HBA: 16

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -1.97

CX Basic pKa: ┄

CX LogP: -0.33

CX LogD: -0.87

Aromatic Rings: ┄

Heavy Atoms: 59

QED Weighted: 0.08

Np Likeness Score: 2.91

References

1. Kumar R, Chaturvedi AK, Shukla PK, Lakshmi V..  (2007)  Antifungal activity in triterpene glycosides from the sea cucumber Actinopyga lecanora.,  17  (15): [PMID:17587569] [10.1016/j.bmcl.2006.12.052]

Source

Source(1):

• Scientific Literature