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

ID: ALA53918

Chembl Id: CHEMBL53918

PubChem CID: 44296088

Max Phase: Preclinical

Molecular Formula: C23H26O10

Molecular Weight: 462.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bipinnatolide-E | CHEMBL53918

Canonical SMILES:  C=C(C(=O)OC)[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/C23H26O10/c1-10-6-14(25)8-11(2)23(28)18(30-13(4)24)15(12(3)20(26)29-5)9-17(32-23)22-19(33-22)16(7-10)31-21(22)27/h6,8,15-19,28H,3,7,9H2,1-2,4-5H3/b10-6-,11-8-/t15-,16-,17?,18-,19-,22-,23+/m1/s1

Standard InChI Key:  LLTUVULYEDWJJW-SFXQMQJESA-N

Alternative Forms

1. Parent:

   

   ALA53918

   methyl 2-[(1R,4R,5R,6S,7Z,10Z,13R,14R)-5-acetyloxy-6-hydroxy-7,11-dimethyl-9,16-dioxo-15,17,18-trioxatetracyclo[11.2.2.12,6.01,14]octadeca-7,10-dien-4-yl]prop-2-enoate

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: 462.45

Molecular Weight (Monoisotopic): 462.1526

AlogP: 0.67

#Rotatable Bonds: 3

Polar Surface Area: 137.96

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.50

CX Basic pKa: ┄

CX LogP: 1.88

CX LogD: 1.87

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: 2.81

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