ID: ALA375269

Max Phase: Preclinical

Molecular Formula: C47H68O15

Molecular Weight: 873.05

Molecule Type: Small molecule

Representations

Synonyms (1): OSW-1
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc(C(=O)O[C@H]2[C@H](O[C@@H]3[C@@H](OC(C)=O)[C@H](O[C@H]4C[C@H]5[C@@H]6CC=C7C[C@@H](O)CC[C@]7(C)[C@H]6CC[C@]5(C)[C@@]4(O)[C@H](C)C(=O)CCC(C)C)OC[C@@H]3O)OC[C@@H](O)[C@@H]2O)cc1

Standard InChI:  InChI=1S/C47H68O15/c1-24(2)8-15-34(50)25(3)47(55)37(21-33-31-14-11-28-20-29(49)16-18-45(28,5)32(31)17-19-46(33,47)6)60-44-41(59-26(4)48)39(36(52)23-58-44)62-43-40(38(53)35(51)22-57-43)61-42(54)27-9-12-30(56-7)13-10-27/h9-13,24-25,29,31-33,35-41,43-44,49,51-53,55H,8,14-23H2,1-7H3/t25-,29+,31-,32+,33+,35-,36+,37+,38+,39+,40-,41-,43+,44+,45+,46+,47-/m1/s1

Standard InChI Key:  MPXTYZZFIJTPPA-MKQTXCTDSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 873.05

Molecular Weight (Monoisotopic): 872.4558

AlogP: 4.02

#Rotatable Bonds: 13

Polar Surface Area: 216.97

Molecular Species: NEUTRAL

HBA: 15

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.56

CX Basic pKa:

CX LogP: 4.61

CX LogD: 4.61

Aromatic Rings: 1

Heavy Atoms: 62

QED Weighted: 0.14

Np Likeness Score: 1.82

References

1. Morzycki JW, Wojtkielewicz A, Wołczyński S..  (2004)  Synthesis of analogues of a potent antitumor saponin OSW-1.,  14  (12): [PMID:15149699] [10.1016/j.bmcl.2004.03.102]

2. Wojtkielewicz A, Długosz M, Maj J, Morzycki JW, Nowakowski M, Renkiewicz J, Strnad M, Swaczynová J, Wilczewska AZ, Wójcik J..  (2007)  New analogues of the potent cytotoxic saponin OSW-1.,  50  (15): [PMID:17608396] [10.1021/jm0613572]

3. Kuroda M, Mimaki Y, Yokosuka A, Sashida Y, Beutler JA..  (2001)  Cytotoxic cholestane glycosides from the bulbs of Ornithogalum saundersiae.,  64  (1): [PMID:11170674] [10.1021/np0003084]

4. Maj J, Morzycki JW, Rárová L, Oklest'ková J, Strnad M, Wojtkielewicz A..  (2011)  Synthesis and biological activity of 22-deoxo-23-oxa analogues of saponin OSW-1.,  54  (9): [PMID:21438635] [10.1021/jm101648h]

5. Yamada R, Takeshita T, Hiraizumi M, Shinohe D, Ohta Y, Sakurai K..  (2014)  Fluorescent analog of OSW-1 and its cellular localization.,  24  (7): [PMID:24613377] [10.1016/j.bmcl.2014.02.009]

6. Kimura M, Sasaki K, Fukutani Y, Yoshida H, Ohsawa I, Yohda M, Sakurai K..  (2019)  Anticancer saponin OSW-1 is a novel class of selective Golgi stress inducer.,  29  (14): [PMID:31126855] [10.1016/j.bmcl.2019.05.022]

Source

Source(1):

• Scientific Literature