9-{2'-Azido-5'-O-[N-(D-biotinoyl)sulfamoyl]-2'-deoxy-beta-D-arabinofuranosyl}adenine triethylammonium Salt

ID: ALA4299213

PubChem CID: 145948788

Max Phase: Preclinical

Molecular Formula: C26H43N13O6S2

Molecular Weight: 596.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CC.[N-]=[N+]=N[C@H]1[C@H](O)[C@@H](CNS(=O)(=O)NC(=O)CCCC[C@@H]2SC[C@@H]3NC(=O)N[C@@H]32)O[C@H]1n1cnc2c(N)ncnc21

Standard InChI:  InChI=1S/C20H28N12O6S2.C6H15N/c21-17-15-18(24-7-23-17)32(8-25-15)19-14(29-31-22)16(34)10(38-19)5-26-40(36,37)30-12(33)4-2-1-3-11-13-9(6-39-11)27-20(35)28-13;1-4-7(5-2)6-3/h7-11,13-14,16,19,26,34H,1-6H2,(H,30,33)(H2,21,23,24)(H2,27,28,35);4-6H2,1-3H3/t9-,10+,11-,13-,14-,16+,19+;/m0./s1

Standard InChI Key:  CQNJLEJAKSCPCP-GEJZKSIJSA-N

Molfile:  

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M  CHG  2   2   1   3  -1
M  END

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: 596.66

Molecular Weight (Monoisotopic): 596.1696

AlogP: -0.98

#Rotatable Bonds: 11

Polar Surface Area: 264.24

Molecular Species: ACID

HBA: 13

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -10.45

CX Basic pKa: 4.99

CX LogP: -4.02

CX LogD: -3.05

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.06

Np Likeness Score: 0.09

References

1. Bockman MR, Kalinda AS, Petrelli R, De la Mora-Rey T, Tiwari D, Liu F, Dawadi S, Nandakumar M, Rhee KY, Schnappinger D, Finzel BC, Aldrich CC..  (2015)  Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors.,  58  (18): [PMID:26299766] [10.1021/acs.jmedchem.5b00719]

Source

Source(1):

• Scientific Literature