(1S,2S,3R,4R)-3-[(S)-1-Acetamido-2-ethylbutyl]-2-[[3-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)propyl]carbamoyloxy]-4-guanidinocyclopentane-1-carboxylic acid

ID: ALA4288995

Chembl Id: CHEMBL4288995

PubChem CID: 71811563

Max Phase: Preclinical

Molecular Formula: C28H41N5O9

Molecular Weight: 591.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(CC)[C@H](NC(C)=O)[C@@H]1[C@H](OC(=O)NCCCOC(=O)/C=C/c2ccc(O)c(O)c2)[C@@H](C(=O)O)C[C@H]1NC(=N)N

Standard InChI:  InChI=1S/C28H41N5O9/c1-4-17(5-2)24(32-15(3)34)23-19(33-27(29)30)14-18(26(38)39)25(23)42-28(40)31-11-6-12-41-22(37)10-8-16-7-9-20(35)21(36)13-16/h7-10,13,17-19,23-25,35-36H,4-6,11-12,14H2,1-3H3,(H,31,40)(H,32,34)(H,38,39)(H4,29,30,33)/b10-8+/t18-,19+,23+,24-,25+/m0/s1

Standard InChI Key:  DOIYAGBAFZCYFH-KWKBSNTCSA-N

Alternative Forms

1. Parent:

   

   ALA4288995

   (1S,2S,3S,4R)-3-[(1S)-1-acetamido-2-ethylbutyl]-4-(diaminomethylideneamino)-2-[3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropylcarbamoyloxy]cyclopentane-1-carboxylic acid

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: 591.66

Molecular Weight (Monoisotopic): 591.2904

AlogP: 1.65

#Rotatable Bonds: 14

Polar Surface Area: 233.39

Molecular Species: ZWITTERION

HBA: 9

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.44

CX Basic pKa: 12.64

CX LogP: 0.00

CX LogD: 0.00

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.04

Np Likeness Score: 0.58

References

1. Wang PC, Chiu DC, Jan JT, Huang WI, Tseng YC, Li TT, Cheng TJ, Tsai KC, Fang JM..  (2018)  Peramivir conjugates as orally available agents against influenza H275Y mutant.,  145  [PMID:29324342] [10.1016/j.ejmech.2017.12.072]

Source

Source(1):

• Scientific Literature