ID: ALA342155

Max Phase: Preclinical

Molecular Formula: C30H42N2O4S

Molecular Weight: 526.74

Molecule Type: Small molecule

Representations

Synonyms (1): 6,6'-Dihydroxythiobinupharidine
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@@H]1CC[C@@H](c2ccoc2)N2[C@H]1CC[C@@]1(CS[C@@]3(CC[C@H]4[C@H](C)CC[C@@H](c5ccoc5)N4[C@@H]3O)C1)[C@H]2O

Standard InChI:  InChI=1S/C30H42N2O4S/c1-19-3-5-25(21-9-13-35-15-21)31-23(19)7-11-29(27(31)33)17-30(37-18-29)12-8-24-20(2)4-6-26(32(24)28(30)34)22-10-14-36-16-22/h9-10,13-16,19-20,23-28,33-34H,3-8,11-12,17-18H2,1-2H3/t19-,20-,23+,24+,25+,26+,27-,28-,29-,30+/m1/s1

Standard InChI Key:  DYEOLAMWQVWASS-XKCSGWQSSA-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: 526.74

Molecular Weight (Monoisotopic): 526.2865

AlogP: 5.94

#Rotatable Bonds: 2

Polar Surface Area: 73.22

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.64

CX Basic pKa: 8.09

CX LogP: 5.43

CX LogD: 4.48

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.50

Np Likeness Score: 1.54

References

1. Matsuda H, Morikawa T, Oda M, Asao Y, Yoshikawa M..  (2003)  Potent anti-metastatic activity of dimeric sesquiterpene thioalkaloids from the rhizome of Nuphar pumilum.,  13  (24): [PMID:14643343] [10.1016/j.bmcl.2003.09.019]

2. Matsuda H, Yoshida K, Miyagawa K, Nemoto Y, Asao Y, Yoshikawa M..  (2006)  Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity.,  16  (6): [PMID:16413779] [10.1016/j.bmcl.2005.12.032]

3. Dalvie ED, Gopas J, Golan-Goldhirsh A, Osheroff N..  (2019)  6,6'-Dihydroxythiobinupharidine as a poison of human type II topoisomerases.,  29  (15): [PMID:31182315] [10.1016/j.bmcl.2019.06.003]

4. Rodrigues L, Tilve SG, Majik MS..  (2021)  Synthetic access to thiolane-based therapeutics and biological activity studies.,  224  [PMID:34237621] [10.1016/j.ejmech.2021.113659]

Source

Source(1):

• Scientific Literature