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

ID: ALA5283364

Max Phase: Preclinical

Molecular Formula: C17H26N4O8

Molecular Weight: 414.42

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](N)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/C17H26N4O8/c1-7(2)5-8(18)14(25)20-12(16(26)27)10-6-9(22)13(24)15(29-10)21-4-3-11(23)19-17(21)28/h3-4,7-10,12-13,15,22,24H,5-6,18H2,1-2H3,(H,20,25)(H,26,27)(H,19,23,28)/t8-,9+,10-,12-,13+,15+/m0/s1

Standard InChI Key:  ZZTILVFYKBCCCO-ZWPBKHOASA-N

Molfile:  

 
     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    3.2154   -0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    0.6189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    1.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    1.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    0.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2263   -0.3768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    1.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.2064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7864    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7864    1.4440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -0.6185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6443    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  8  7  1  0
  8  2  1  0
  9  8  1  1
 10  9  1  0
 10 11  1  6
 12 10  1  0
 12 13  1  6
 14 12  1  0
 15 14  1  0
 15 16  1  0
  9 16  1  0
 15 17  1  6
 15 18  1  0
 18 19  1  6
 19 20  1  0
 19 21  2  0
 18 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283364

   ---

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: 414.42

Molecular Weight (Monoisotopic): 414.1751

AlogP: -2.51

#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: 3.65

CX Basic pKa: 8.41

CX LogP: -4.32

CX LogD: -4.36

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.28

Np Likeness Score: 0.87

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