ID: ALA1163081

Max Phase: Preclinical

Molecular Formula: C16H25N7O7S

Molecular Weight: 459.49

Molecule Type: Small molecule

Representations

Synonyms (1): Leusa
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)C[C@H](N)C(=O)NS(=O)(=O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H25N7O7S/c1-7(2)3-8(17)15(26)22-31(27,28)29-4-9-11(24)12(25)16(30-9)23-6-21-10-13(18)19-5-20-14(10)23/h5-9,11-12,16,24-25H,3-4,17H2,1-2H3,(H,22,26)(H2,18,19,20)/t8-,9+,11+,12+,16+/m0/s1

Standard InChI Key:  XFEDFDTWJLGMBO-LEJQEAHTSA-N

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

Properties

Molecular Weight: 459.49

Molecular Weight (Monoisotopic): 459.1536

AlogP: -2.22

#Rotatable Bonds: 8

Polar Surface Area: 217.80

Molecular Species: ACID

HBA: 13

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.74

CX Basic pKa: 6.80

CX LogP: -2.64

CX LogD: -2.65

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: 0.73

References

1. Van de Vijver P, Vondenhoff GH, Denivelle S, Rozenski J, Verhaegen J, Van Aerschot A, Herdewijn P..  (2009)  Antibacterial 5'-O-(N-dipeptidyl)-sulfamoyladenosines.,  17  (1): [PMID:19070499] [10.1016/j.bmc.2008.11.054]

2. Van de Vijver P, Ostrowski T, Sproat B, Goebels J, Rutgeerts O, Van Aerschot A, Waer M, Herdewijn P..  (2008)  Aminoacyl-tRNA synthetase inhibitors as potent and synergistic immunosuppressants.,  51  (10): [PMID:18438987] [10.1021/jm8000746]

3. Zhang B, De Graef S, Nautiyal M, Pang L, Gadakh B, Froeyen M, Van Mellaert L, Strelkov SV, Weeks SD, Van Aerschot A..  (2018)  Family-wide analysis of aminoacyl-sulfamoyl-3-deazaadenosine analogues as inhibitors of aminoacyl-tRNA synthetases.,  148  [PMID:29477072] [10.1016/j.ejmech.2018.02.013]

4. Yoon S, Kim SE, Kim JH, Yoon I, Tran PT, Ann J, Kim C, Byun WS, Lee S, Kim S, Lee J, Lee J..  (2019)  Structure-activity relationship of leucyladenylate sulfamate analogues as leucyl-tRNA synthetase (LRS)-targeting inhibitors of Mammalian target of rapamycin complex 1 (mTORC1).,  27  (6): [PMID:30755350] [10.1016/j.bmc.2019.01.037]

5. Nautiyal M, De Graef S, Pang L, Gadakh B, Strelkov SV, Weeks SD, Van Aerschot A..  (2019)  Comparative analysis of pyrimidine substituted aminoacyl-sulfamoyl nucleosides as potential inhibitors targeting class I aminoacyl-tRNA synthetases.,  173  [PMID:30995568] [10.1016/j.ejmech.2019.04.003]

6. Yoon S,Kim JH,Kim SE,Kim C,Tran PT,Ann J,Koh Y,Jang J,Kim S,Moon HS,Kim WK,Lee S,Lee J,Kim S,Lee J.  (2016)  Discovery of Leucyladenylate Sulfamates as Novel Leucyl-tRNA Synthetase (LRS)-Targeted Mammalian Target of Rapamycin Complex 1 (mTORC1) Inhibitors.,  59  (22): [PMID:27933890] [10.1021/acs.jmedchem.6b01190]

Source

Source(1):

• Scientific Literature