Biselyngbyolide B

ID: ALA4216774

Chembl Id: CHEMBL4216774

PubChem CID: 76900277

Max Phase: Preclinical

Molecular Formula: C27H40O4

Molecular Weight: 428.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C/C/C(C)=C\[C@H]1C/C=C/C=C/C[C@H](C)/C=C(\C)[C@@H](OC)C/C=C/[C@@H](O)CC(=O)O1

Standard InChI:  InChI=1S/C27H40O4/c1-6-7-13-22(3)19-25-16-11-9-8-10-14-21(2)18-23(4)26(30-5)17-12-15-24(28)20-27(29)31-25/h6-12,15,18-19,21,24-26,28H,13-14,16-17,20H2,1-5H3/b7-6+,10-8+,11-9+,15-12+,22-19-,23-18+/t21-,24+,25+,26-/m0/s1

Standard InChI Key:  DVYYXLNVAXSASA-BEVCVMOBSA-N

Alternative Forms

1. Parent:

   

   ALA4216774

   (4s,5e,8s,9e,11s,13e,15e,18r)-4-Hydroxy-8-Methoxy-9,11-Dimethyl-18-[(1z,4e)-2-Methylhexa-1,4-Dien-1-Yl]oxacyclooctadeca-5,9,13,15-Tetraen-2-One

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: 428.61

Molecular Weight (Monoisotopic): 428.2927

AlogP: 6.01

#Rotatable Bonds: 4

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.74

CX LogD: 5.74

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: 2.73

References

1. Sato E, Morita M, Ogawa H, Iwatsuki M, Hokari R, Ishiyama A, Ōmura S, Iwasaki A, Suenaga K..  (2018)  Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca²⁺ pump inhibitor from marine cyanobacteria.,  28  (3): [PMID:29292225] [10.1016/j.bmcl.2017.12.050]

2. Peterková L, Kmoníčková E, Ruml T, Rimpelová S..  (2020)  Sarco/Endoplasmic Reticulum Calcium ATPase Inhibitors: Beyond Anticancer Perspective.,  63  (5): [PMID:32030976] [10.1021/acs.jmedchem.9b01509]

3. Govindarajan M..  (2018)  Amphiphilic glycoconjugates as potential anti-cancer chemotherapeutics.,  143  [PMID:29126728] [10.1016/j.ejmech.2017.10.015]

Source

Source(1):

• Scientific Literature