(E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-3-methyl-but-2-enoic acid ethyl ester

ID: ALA315230

Chembl Id: CHEMBL315230

PubChem CID: 11728420

Max Phase: Preclinical

Molecular Formula: C19H32O7

Molecular Weight: 372.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C(\C)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C19H32O7/c1-5-24-16(21)7-10(2)6-14-18(23)17(22)13(9-25-14)8-15-19(26-15)11(3)12(4)20/h7,11-15,17-20,22-23H,5-6,8-9H2,1-4H3/b10-7+/t11-,12-,13-,14-,15-,17+,18-,19-/m0/s1

Standard InChI Key:  KVSTXNJARPQHCO-ALDWRELFSA-N

Alternative Forms

1. Parent:

   

   ALA315230

   ethyl (E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoate

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: 372.46

Molecular Weight (Monoisotopic): 372.2148

AlogP: 0.80

#Rotatable Bonds: 8

Polar Surface Area: 108.75

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: ┄

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.33

Np Likeness Score: 2.00

References

1. Brown P, Best DJ, Broom NJ, Cassels R, O'Hanlon PJ, Mitchell TJ, Osborne NF, Wilson JM..  (1997)  The chemistry of pseudomonic acid. 18. Heterocyclic replacement of the alpha,beta-unsaturated ester: synthesis, molecular modeling, and antibacterial activity.,  40  (16): [PMID:9258363] [10.1021/jm960738k]

Source

Source(1):

• Scientific Literature