(3R,4R,5S)-4-Acetamido-5-((4-(cyclohexylthio)benzyl)-amino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic Acid

ID: ALA4292761

Chembl Id: CHEMBL4292761

PubChem CID: 145988967

Max Phase: Preclinical

Molecular Formula: C27H40N2O4S

Molecular Weight: 488.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(CC)O[C@@H]1C=C(C(=O)O)C[C@H](NCc2ccc(SC3CCCCC3)cc2)[C@H]1NC(C)=O

Standard InChI:  InChI=1S/C27H40N2O4S/c1-4-21(5-2)33-25-16-20(27(31)32)15-24(26(25)29-18(3)30)28-17-19-11-13-23(14-12-19)34-22-9-7-6-8-10-22/h11-14,16,21-22,24-26,28H,4-10,15,17H2,1-3H3,(H,29,30)(H,31,32)/t24-,25+,26+/m0/s1

Standard InChI Key:  CISGUQWJHJWBKI-JIMJEQGWSA-N

Alternative Forms

1. Parent:

   

   ALA4292761

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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: 488.69

Molecular Weight (Monoisotopic): 488.2709

AlogP: 5.06

#Rotatable Bonds: 11

Polar Surface Area: 87.66

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.08

CX Basic pKa: 8.78

CX LogP: 2.33

CX LogD: 2.32

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.40

Np Likeness Score: 0.17

References

1. Zhang J, Murugan NA, Tian Y, Bertagnin C, Fang Z, Kang D, Kong X, Jia H, Sun Z, Jia R, Gao P, Poongavanam V, Loregian A, Xu W, Ma X, Ding X, Huang B, Zhan P, Liu X..  (2018)  Structure-Based Optimization of N-Substituted Oseltamivir Derivatives as Potent Anti-Influenza A Virus Agents with Significantly Improved Potency against Oseltamivir-Resistant N1-H274Y Variant.,  61  (22): [PMID:30365885] [10.1021/acs.jmedchem.8b01065]

Source

Source(1):

• Scientific Literature