[2-(6-Hydroxy-benzothiazol-2-yl)-thiazole-4-carbonyl]-sulfamic acid 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

ID: ALA1235965

PubChem CID: 135403658

Max Phase: Preclinical

Molecular Formula: C21H18N8O8S3

Molecular Weight: 606.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COS(=O)(=O)NC(=O)c2csc(-c3nc4ccc(O)cc4s3)n2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C21H18N8O8S3/c22-16-13-17(24-6-23-16)29(7-25-13)21-15(32)14(31)11(37-21)4-36-40(34,35)28-18(33)10-5-38-19(27-10)20-26-9-2-1-8(30)3-12(9)39-20/h1-3,5-7,11,14-15,21,30-32H,4H2,(H,28,33)(H2,22,23,24)/t11-,14-,15-,21-/m1/s1

Standard InChI Key:  LJLYTUYNVSHXQB-SOONXTGKSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1235965

   ---

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: 606.62

Molecular Weight (Monoisotopic): 606.0410

AlogP: 0.16

#Rotatable Bonds: 7

Polar Surface Area: 237.79

Molecular Species: ACID

HBA: 17

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.71

CX Basic pKa: 4.92

CX LogP: -0.83

CX LogD: -0.43

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.17

Np Likeness Score: -0.23

References

1. Branchini BR, Murtiashaw MH, Carmody JN, Mygatt EE, Southworth TL..  (2005)  Synthesis of an N-acyl sulfamate analog of luciferyl-AMP: a stable and potent inhibitor of firefly luciferase.,  15  (17): [PMID:15990297] [10.1016/j.bmcl.2005.05.115]

Source

Source(1):

• Scientific Literature