6-hydroxy-4-isopropenyl-7,11-dimethyl-9,16-dioxo-(2S,4R,5R,6S,13R)-15,17,18-trioxatetracyclo[11.2.2.12,6.01,14]octadeca-7,10-dien-5-yl acetate (Bipinnatolide-B)

ID: ALA48893

Chembl Id: CHEMBL48893

PubChem CID: 44295868

Max Phase: Preclinical

Molecular Formula: C22H26O8

Molecular Weight: 418.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bipinnatolide-B | Bipinnatolide-B|CHEMBL48893

Canonical SMILES:  C=C(C)[C@H]1CC2O[C@@](O)(/C(C)=C\C(=O)/C=C(/C)C[C@H]3OC(=O)[C@@]24O[C@H]34)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C22H26O8/c1-10(2)15-9-17-21-19(30-21)16(28-20(21)25)7-11(3)6-14(24)8-12(4)22(26,29-17)18(15)27-13(5)23/h6,8,15-19,26H,1,7,9H2,2-5H3/b11-6-,12-8-/t15-,16-,17?,18-,19-,21-,22+/m1/s1

Standard InChI Key:  HMJCTYOUGGYKMA-SVRAUSSSSA-N

Alternative Forms

1. Parent:

   

   ALA48893

   Bipinnatolide-B

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: 418.44

Molecular Weight (Monoisotopic): 418.1628

AlogP: 1.52

#Rotatable Bonds: 2

Polar Surface Area: 111.66

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.50

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: 2.89

References

1. Abramson SN, Trischman JA, Tapiolas DM, Harold EE, Fenical W, Taylor P..  (1991)  Structure/activity and molecular modeling studies of the lophotoxin family of irreversible nicotinic receptor antagonists.,  34  (6): [PMID:1676426] [10.1021/jm00110a007]

Source

Source(1):

• Scientific Literature