2-hydroxy-4-(1-hydroxymethylvinyl)-7,12-dimethyl-17-oxo-(2S,4R,5R,14R)-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-5-yl acetate

ID: ALA298795

Chembl Id: CHEMBL298795

PubChem CID: 44296237

Max Phase: Preclinical

Molecular Formula: C22H26O9

Molecular Weight: 434.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(CO)[C@H]1C[C@H](O)[C@@]23O[C@@H]2[C@@H](C[C@]2(C)O[C@H]2c2cc(C)c(o2)[C@@H]1OC(C)=O)OC3=O

Standard InChI:  InChI=1S/C22H26O9/c1-9-5-13-18-21(4,30-18)7-14-19-22(31-19,20(26)29-14)15(25)6-12(10(2)8-23)17(16(9)28-13)27-11(3)24/h5,12,14-15,17-19,23,25H,2,6-8H2,1,3-4H3/t12-,14-,15+,17-,18+,19-,21+,22-/m1/s1

Standard InChI Key:  JHGPMYNXJUTSNA-UZSUROCWSA-N

Alternative Forms

1. Parent:

   

   ALA298795

   [(1R,2S,4R,5R,10R,12S,14R,15R)-2-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-5-yl] acetate

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: 434.44

Molecular Weight (Monoisotopic): 434.1577

AlogP: 1.40

#Rotatable Bonds: 3

Polar Surface Area: 131.26

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.61

CX Basic pKa: ┄

CX LogP: 0.25

CX LogD: 0.25

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: 3.20

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