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

ID: ALA5285803

Max Phase: Preclinical

Molecular Formula: C20H24N4O9

Molecular Weight: 464.43

Names and Identifiers

Canonical SMILES:  N[C@@H](Cc1ccc(O)cc1)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/C20H24N4O9/c21-11(7-9-1-3-10(25)4-2-9)17(29)23-15(19(30)31)13-8-12(26)16(28)18(33-13)24-6-5-14(27)22-20(24)32/h1-6,11-13,15-16,18,25-26,28H,7-8,21H2,(H,23,29)(H,30,31)(H,22,27,32)/t11-,12+,13-,15-,16+,18+/m0/s1

Standard InChI Key:  ZODHMHLWKHYDGU-QGJUDNFOSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5285803

   ---

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: 464.43

Molecular Weight (Monoisotopic): 464.1543

AlogP: -2.61

#Rotatable Bonds: 7

Polar Surface Area: 217.20

Molecular Species: ACID

HBA: 10

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.50

CX Basic pKa: 8.01

CX LogP: -4.22

CX LogD: -4.31

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: 0.86

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