5'-O-[N-(D-Biotinoyl)sulfamoyl]-beta-2'-methyladenosine Triethylammonium Salt

ID: ALA4299218

PubChem CID: 145948829

Max Phase: Preclinical

Molecular Formula: C27H45N9O8S2

Molecular Weight: 586.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CC.C[C@@]1(O)[C@H](O)[C@@H](COS(=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/C21H30N8O8S2.C6H15N/c1-21(33)16(31)11(37-19(21)29-9-25-15-17(22)23-8-24-18(15)29)6-36-39(34,35)28-13(30)5-3-2-4-12-14-10(7-38-12)26-20(32)27-14;1-4-7(5-2)6-3/h8-12,14,16,19,31,33H,2-7H2,1H3,(H,28,30)(H2,22,23,24)(H2,26,27,32);4-6H2,1-3H3/t10-,11+,12-,14-,16+,19+,21+;/m0./s1

Standard InChI Key:  WHDYVVLMXPIFMJ-ZBLFTYSOSA-N

Molfile:  

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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: 586.65

Molecular Weight (Monoisotopic): 586.1628

AlogP: -1.48

#Rotatable Bonds: 10

Polar Surface Area: 232.91

Molecular Species: ACID

HBA: 14

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.05

CX Basic pKa: 4.92

CX LogP: -2.98

CX LogD: -2.74

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.14

Np Likeness Score: 0.38

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