4-((1E,3E)-4-((2R,5r)-5-((2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-ylthio)-1,3-dioxan-2-yl)buta-1,3-dienyl)-3-fluorobenzonitrile

ID: ALA475786

Chembl Id: CHEMBL475786

Cas Number: 329744-44-7

PubChem CID: 6475890

Max Phase: Phase

Molecular Formula: C27H25F3N4O3S

Molecular Weight: 542.58

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CS-758 | R-120758 | Embeconazole|CS-758|Embeconazole [INN]|329744-44-7|UNII-02B953TLAI|02B953TLAI|R-120758|4-[(1E,3E)-4-[5-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]sulfanyl-1,3-dioxan-2-yl]buta-1,3-dienyl]-3-fluorobenzonitrile|4-((1E,3E)-4-(trans-5-(((2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl)sulfanyl)-1,3-dioxan-2-yl)buta-1,3-dien-1-yl)-3-fluorobenzonitrile|4-((1E,3E)-4-(TRANS-5-(((1R,2R)-2-(2,4-DIFLUOROPHENYL)-2-HYDROXY-1-METHShow More⌵

Canonical SMILES:  C[C@@H](S[C@H]1CO[C@H](/C=C/C=C/c2ccc(C#N)cc2F)OC1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F

Standard InChI:  InChI=1S/C27H25F3N4O3S/c1-18(27(35,15-34-17-32-16-33-34)23-9-8-21(28)11-25(23)30)38-22-13-36-26(37-14-22)5-3-2-4-20-7-6-19(12-31)10-24(20)29/h2-11,16-18,22,26,35H,13-15H2,1H3/b4-2+,5-3+/t18-,22-,26-,27-/m1/s1

Standard InChI Key:  XSRKBFUVSRRJDX-GGZJQHSXSA-N

Alternative Forms

1. Parent:

   

   ALA475786

   EMBECONAZOLE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 542.58

Molecular Weight (Monoisotopic): 542.1599

AlogP: 4.59

#Rotatable Bonds: 9

Polar Surface Area: 93.19

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.75

CX Basic pKa: 2.00

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.40

Np Likeness Score: -0.75

References

1. Uchida T, Kagoshima Y, Konosu T..  (2009)  Amide analogs of antifungal dioxane-triazole derivatives: synthesis and in vitro activities.,  19  (7): [PMID:19269821] [10.1016/j.bmcl.2009.02.036]

2. Kagoshima Y, Mori M, Suzuki E, Shibayama T, Iida T, Kamai Y, Konosu T..  (2009)  Synthesis, cleavage, and antifungal activity of a number of novel, water-soluble ester prodrugs of antifungal triazole CS-758.,  19  (13): [PMID:19467867] [10.1016/j.bmcl.2009.04.135]

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. Ghobadi E, Saednia S, Emami S..  (2022)  Synthetic approaches and structural diversity of triazolylbutanols derived from voriconazole in the antifungal drug development.,  231  [PMID:35134679] [10.1016/j.ejmech.2022.114161]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names