3-Hydroxy-11-isopropyl-3-methyl-7-oxo-6,16-dioxa-tricyclo[11.2.1.1*5,8*]heptadeca-1(15),13-diene-14-carboxylic acid methyl ester (hexahydropukalide)

ID: ALA53408

Chembl Id: CHEMBL53408

PubChem CID: 44296144

Max Phase: Preclinical

Molecular Formula: C21H30O6

Molecular Weight: 378.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc2oc1C[C@@H](C(C)C)CCC1C[C@@H](C[C@](C)(O)C2)OC1=O

Standard InChI:  InChI=1S/C21H30O6/c1-12(2)13-5-6-14-7-15(27-19(14)22)10-21(3,24)11-16-9-17(20(23)25-4)18(8-13)26-16/h9,12-15,24H,5-8,10-11H2,1-4H3/t13-,14?,15-,21-/m0/s1

Standard InChI Key:  LZBSJKGMAVYZOA-ZFKDUMRVSA-N

Alternative Forms

1. Parent:

   

   ALA53408

   methyl (3S,5S,11S)-3-hydroxy-3-methyl-7-oxo-11-propan-2-yl-6,16-dioxatricyclo[11.2.1.15,8]heptadeca-1(15),13-diene-14-carboxylate

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: 378.47

Molecular Weight (Monoisotopic): 378.2042

AlogP: 3.29

#Rotatable Bonds: 2

Polar Surface Area: 85.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: 1.81

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