(4aR,6S,7R,7aS)-7-[2-((2S,3S)-2-Amino-3-methyl-pentanoylsulfamoyl)-acetylamino]-4-carbamoyl-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindine-7-carboxylic acid methyl ester

ID: ALA74872

Chembl Id: CHEMBL74872

PubChem CID: 44312774

Max Phase: Preclinical

Molecular Formula: C20H33N5O8S

Molecular Weight: 503.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](N)C(=O)NS(=O)(=O)CC(=O)N[C@]1(C(=O)OC)[C@@H]2CN(C)C=C(C(N)=O)[C@@H]2C[C@@H]1O

Standard InChI:  InChI=1S/C20H33N5O8S/c1-5-10(2)16(21)18(29)24-34(31,32)9-15(27)23-20(19(30)33-4)13-8-25(3)7-12(17(22)28)11(13)6-14(20)26/h7,10-11,13-14,16,26H,5-6,8-9,21H2,1-4H3,(H2,22,28)(H,23,27)(H,24,29)/t10-,11-,13+,14-,16-,20+/m0/s1

Standard InChI Key:  PSXYYVPGRFVMCG-KULQGWMCSA-N

Alternative Forms

1. Parent:

   

   ALA74872

   (4aR,6S,7R,7aS)-7-[2-((2S,3S)-2-Amino-3-methyl-pentanoylsulfamoyl)-acetylamino]-4-carbamoyl-6-hydroxy-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-[2]pyrindine-7-carboxylic acid methyl ester

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: 503.58

Molecular Weight (Monoisotopic): 503.2050

AlogP: -2.85

#Rotatable Bonds: 9

Polar Surface Area: 211.22

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.59

CX Basic pKa: 6.95

CX LogP: -3.85

CX LogD: -3.88

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.20

Np Likeness Score: 0.27

References

1. Banwell MG, Crasto CF, Easton CJ, Forrest AK, Karoli T, March DR, Mensah L, Nairn MR, O'Hanlon PJ, Oldham MD, Yue W..  (2000)  Analogues of SB-203207 as inhibitors of tRNA synthetases.,  10  (20): [PMID:11055334] [10.1016/s0960-894x(00)00456-x]

2. Zhao Y, Wang Q, Meng Q, Ding D, Yang H, Gao G, Li D, Zhu W, Zhou H..  (2012)  Identification of Trypanosoma brucei leucyl-tRNA synthetase inhibitors by pharmacophore- and docking-based virtual screening and synthesis.,  20  (3): [PMID:22249121] [10.1016/j.bmc.2011.12.035]

Source

Source(1):

• Scientific Literature