(2R,4S,5R)-5-((1R,2R)-1-acetamido-2-methoxy-2-methylpentyl)-4-(prop-1-enyl)pyrrolidine-2-carboxylic acid

ID: ALA473062

Chembl Id: CHEMBL473062

Cas Number: 335679-69-1

PubChem CID: 6451053

Max Phase: Preclinical

Molecular Formula: C17H30N2O4

Molecular Weight: 326.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: A-315675 | A-315675|335679-69-1|UNII-H8E590FKGW|D-Proline, 5-((1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl)-4-(1Z)-1-propenyl-, (4S,5R)-|A 315675|H8E590FKGW|CHEMBL473062|(2R,4S,5R)-5-[(1R,2S)-1-acetamido-2-methoxy-2-methylpentyl]-4-[(Z)-prop-1-enyl]pyrrolidine-2-carboxylic acid|(2R,4S,5R)-5-((1R,2S)-1-Acetamido-2-methoxy-2-methylpentyl)-4-((Z)-prop-1-en-1-yl)pyrrolidine-2-carboxylic acid|5-((2S,1R)-1-(Acetylamino)-2-methoxy-2-methylpentyl)(4S,2R)-4-(prop-1-enyl)pyrrolidine-2-carboxylic acid|Show More⌵

Canonical SMILES:  C/C=C\[C@@H]1C[C@H](C(=O)O)N[C@H]1[C@@H](NC(C)=O)[C@](C)(CCC)OC

Standard InChI:  InChI=1S/C17H30N2O4/c1-6-8-12-10-13(16(21)22)19-14(12)15(18-11(3)20)17(4,23-5)9-7-2/h6,8,12-15,19H,7,9-10H2,1-5H3,(H,18,20)(H,21,22)/b8-6-/t12-,13-,14-,15-,17+/m1/s1

Standard InChI Key:  UUVKABIGWGMYCE-FLMGFEAJSA-N

Alternative Forms

1. Parent:

   

   ALA473062

   D-Proline, 5-((1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl)-4-(1Z)-1-propenyl-, (4S,5R)-

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: 326.44

Molecular Weight (Monoisotopic): 326.2206

AlogP: 1.70

#Rotatable Bonds: 8

Polar Surface Area: 87.66

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.12

CX Basic pKa: 10.70

CX LogP: -0.92

CX LogD: -0.92

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: 0.87

References

1. Krueger AC, Xu Y, Kati WM, Kempf DJ, Maring CJ, McDaniel KF, Molla A, Montgomery D, Kohlbrenner WE..  (2008)  Synthesis of potent pyrrolidine influenza neuraminidase inhibitors.,  18  (5): [PMID:18242993] [10.1016/j.bmcl.2008.01.048]

2. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

3. Okomo-Adhiambo M, Demmler-Harrison GJ, Deyde VM, Sheu TG, Xu X, Klimov AI, Gubareva LV..  (2010)  Detection of E119V and E119I mutations in influenza A (H3N2) viruses isolated from an immunocompromised patient: challenges in diagnosis of oseltamivir resistance.,  54  (5): [PMID:20194700] [10.1128/aac.01608-09]

4. Nguyen HT, Sheu TG, Mishin VP, Klimov AI, Gubareva LV..  (2010)  Assessment of pandemic and seasonal influenza A (H1N1) virus susceptibility to neuraminidase inhibitors in three enzyme activity inhibition assays.,  54  (9): [PMID:20585136] [10.1128/aac.00581-10]

5. Bhatt B, Böhm R, Kerry PS, Dyason JC, Russell RJ, Thomson RJ, von Itzstein M..  (2012)  Exploring the interactions of unsaturated glucuronides with influenza virus sialidase.,  55  (20): [PMID:23017008] [10.1021/jm301145k]

Source

Source(1):

• Scientific Literature