12-isopropenyl-4,15-dimethyl-10-methylcarbonyloxy-8-oxo-(6R,10S,13R)-3,7,17-trioxatetracyclo[12.2.1.16,9.02,4]octadeca-1 (16),9 (18),14-trien-13-yl acetate (Bipinnatin-G)

ID: ALA301578

Chembl Id: CHEMBL301578

PubChem CID: 44296308

Max Phase: Preclinical

Molecular Formula: C24H28O8

Molecular Weight: 444.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bipinnatin-G | Bipinnatin-G|CHEMBL301578

Canonical SMILES:  C=C(C)[C@H]1C[C@H](OC(C)=O)C2=C[C@@H](C[C@]3(C)O[C@H]3c3cc(C)c(o3)[C@@H]1OC(C)=O)OC2=O

Standard InChI:  InChI=1S/C24H28O8/c1-11(2)16-9-18(28-13(4)25)17-8-15(30-23(17)27)10-24(6)22(32-24)19-7-12(3)20(31-19)21(16)29-14(5)26/h7-8,15-16,18,21-22H,1,9-10H2,2-6H3/t15-,16+,18-,21+,22-,24-/m0/s1

Standard InChI Key:  BSRQZDCQSDYEKJ-SQDRVSCESA-N

Alternative Forms

1. Parent:

   

   ALA301578

   Bipinnatin-G

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

Calculated Properties

Molecular Weight: 444.48

Molecular Weight (Monoisotopic): 444.1784

AlogP: 3.79

#Rotatable Bonds: 3

Polar Surface Area: 104.57

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.84

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: 2.56

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: 2.83

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