methyl 2-[7,12-dimethyl-2,5-di (methylcarbonyloxy)-18-oxo-(2S,4R,5R,12R,14R)-11,19,20-trioxapentacyclo[12.3.2.16,9.01,15.010,12]icosa-6,8,16-trien-4-yl]acrylate (Bipinnatin-I)

ID: ALA298966

Chembl Id: CHEMBL298966

PubChem CID: 44296307

Max Phase: Preclinical

Molecular Formula: C25H28O10

Molecular Weight: 488.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bipinnatin-I | Bipinnatin-I|CHEMBL298966

Canonical SMILES:  C=C(C(=O)OC)[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/C25H28O10/c1-11-7-19-22-25(5,35-22)10-15-8-17(24(29)33-15)18(31-13(3)26)9-16(12(2)23(28)30-6)21(20(11)34-19)32-14(4)27/h7-8,15-16,18,21-22H,2,9-10H2,1,3-6H3/t15-,16+,18-,21+,22-,25-/m0/s1

Standard InChI Key:  DORQEQXBYZYXMV-PNCPNADGSA-N

Alternative Forms

1. Parent:

   

   ALA298966

   Bipinnatin-I

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: 488.49

Molecular Weight (Monoisotopic): 488.1682

AlogP: 2.94

#Rotatable Bonds: 4

Polar Surface Area: 130.87

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.84

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 2.13

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.27

Np Likeness Score: 2.77

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