(2S)-2-((S)-2-amino-3-phenylpropanamido)-2-((2S,4R,5R,6R)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)acetic acid

ID: ALA5269429

Max Phase: Preclinical

Molecular Formula: C20H24N4O8

Molecular Weight: 448.43

Names and Identifiers

Canonical SMILES:  N[C@@H](Cc1ccccc1)C(=O)N[C@H](C(=O)O)[C@@H]1C[C@@H](O)[C@@H](O)[C@H](n2ccc(=O)[nH]c2=O)O1

Standard InChI:  InChI=1S/C20H24N4O8/c21-11(8-10-4-2-1-3-5-10)17(28)23-15(19(29)30)13-9-12(25)16(27)18(32-13)24-7-6-14(26)22-20(24)31/h1-7,11-13,15-16,18,25,27H,8-9,21H2,(H,23,28)(H,29,30)(H,22,26,31)/t11-,12+,13-,15-,16+,18+/m0/s1

Standard InChI Key:  MZWYEBXQQMOLTC-QGJUDNFOSA-N

Molfile:  

 
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   -2.8579    0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 31  1  0
 33 32  2  0
 28 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5269429

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 448.43

Molecular Weight (Monoisotopic): 448.1594

AlogP: -2.31

#Rotatable Bonds: 7

Polar Surface Area: 196.97

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.59

CX Basic pKa: 8.00

CX LogP: -3.92

CX LogD: -4.01

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.27

Np Likeness Score: 0.71

References

1. Serpi M, Ferrari V, Pertusati F..  (2016)  Nucleoside Derived Antibiotics to Fight Microbial Drug Resistance: New Utilities for an Established Class of Drugs?,  59  (23): [PMID:27607900] [10.1021/acs.jmedchem.6b00325]

Source

Source(1):

• Scientific Literature