ID: ALA505513

Max Phase: Preclinical

Molecular Formula: C30H47N5O15

Molecular Weight: 717.73

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  CC(=O)N[C@H]1[C@@H](O[C@@H]2O[C@H](CC(O)[C@H]3O[C@@H](n4ccc(=O)[nH]c4=O)[C@H](O)[C@@H]3O)[C@H](O)[C@H](O)[C@H]2NC(=O)/C=C/CC(C)C)O[C@H](CO)[C@@H](N)[C@@H]1O

Standard InChI:  InChI=1S/C30H47N5O15/c1-11(2)5-4-6-16(39)33-20-23(43)21(41)14(47-29(20)50-28-19(32-12(3)37)22(42)18(31)15(10-36)48-28)9-13(38)26-24(44)25(45)27(49-26)35-8-7-17(40)34-30(35)46/h4,6-8,11,13-15,18-29,36,38,41-45H,5,9-10,31H2,1-3H3,(H,32,37)(H,33,39)(H,34,40,46)/b6-4+/t13?,14-,15-,18-,19-,20-,21+,22+,23-,24+,25-,26-,27-,28-,29+/m1/s1

Standard InChI Key:  VYEWZWBILJHHCU-OMQUDAQFSA-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: 717.73

Molecular Weight (Monoisotopic): 717.3069

AlogP: -5.63

#Rotatable Bonds: 12

Polar Surface Area: 317.61

Molecular Species: NEUTRAL

HBA: 17

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.72

CX Basic pKa: 8.41

CX LogP: -5.02

CX LogD: -5.90

Aromatic Rings: 1

Heavy Atoms: 50

QED Weighted: 0.09

Np Likeness Score: 1.48

References

1. Dini C, Didier-Laurent S, Drochon N, Feteanu S, Guillot JC, Monti F, Uridat E, Zhang J, Aszodi J..  (2002)  Synthesis of sub-micromolar inhibitors of MraY by exploring the region originally occupied by the diazepanone ring in the liposidomycin structure.,  12  (8): [PMID:11934590] [10.1016/s0960-894x(02)00109-9]

2. Dini C, Collette P, Drochon N, Guillot JC, Lemoine G, Mauvais P, Aszodi J..  (2000)  Synthesis of the nucleoside moiety of liposidomycins: elucidation of the pharmacophore of this family of MraY inhibitors.,  10  (16): [PMID:10969981] [10.1016/s0960-894x(00)00349-8]

3. Silva DJ, Bowe CL, Branstrom AA, Baizman ER, Sofia MJ..  (2000)  Synthesis and biological evaluation of analogues of bacterial lipid I.,  10  (24): [PMID:11133098] [10.1016/s0960-894x(00)00583-7]

4. Camarasa MJ, Fernández-Resa P, Garcia-López MT, De las Heras FG, Méndez-Castrillón PP, Alarcón B, Carrasco L..  (1985)  Uridine 5'-diphosphate glucose analogues. Inhibitors of protein glycosylation that show antiviral activity.,  28  (1): [PMID:2981323] [10.1021/jm00379a010]

5. Shi Y, Gerritsma D, Bowes AJ, Capretta A, Werstuck GH..  (2007)  Induction of GRP78 by valproic acid is dependent upon histone deacetylase inhibition.,  17  (16): [PMID:17566732] [10.1016/j.bmcl.2007.06.006]

6. Kitamura A, Someya K, Hata M, Nakajima R, Takemura M..  (2009)  Discovery of a small-molecule inhibitor of {beta}-1,6-glucan synthesis.,  53  (2): [PMID:19015325] [10.1128/aac.00844-08]

7. Bicker KL, Anguish L, Chumanevich AA, Cameron MD, Cui X, Witalison E, Subramanian V, Zhang X, Chumanevich AP, Hofseth LJ, Coonrod SA, Thompson PR..  (2012)  D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.,  3  (12): [PMID:23420624] [10.1021/ml300288d]

8. Mihalyi A, Jamshidi S, Slikas J, Bugg TD..  (2014)  Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.,  22  (17): [PMID:25127465] [10.1016/j.bmc.2014.07.035]

9. Open TG-GATES,  [10.6019/CHEMBL3885861]

Source

Source(2):

• Scientific Literature
• Open TG-GATEs