2-(4-((4-amino-2-methylpyrimidin-5-yl)methyl)-3-methylthiophen-2-yl)ethanol

ID: ALA401772

Chembl Id: CHEMBL401772

Cas Number: 334687-37-5

PubChem CID: 10539503

Max Phase: Preclinical

Molecular Formula: C13H17N3OS

Molecular Weight: 263.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-Deazathiamine | 3-Deazathiamine|CHEMBL401772|2-{4-[(4-Amino-2-Methylpyrimidin-5-Yl)methyl]-3-Methylthiophen-2-Yl}ethanol|2-(4-((4-amino-2-methylpyrimidin-5-yl)methyl)-3-methylthiophen-2-yl)ethanol|334687-37-5|0YN|BDBM50373886|Q27451543

Canonical SMILES:  Cc1ncc(Cc2csc(CCO)c2C)c(N)n1

Standard InChI:  InChI=1S/C13H17N3OS/c1-8-11(7-18-12(8)3-4-17)5-10-6-15-9(2)16-13(10)14/h6-7,17H,3-5H2,1-2H3,(H2,14,15,16)

Standard InChI Key:  HLBXMICRXICHJQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA401772

   3-DEAZATHIAMINE

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: 263.37

Molecular Weight (Monoisotopic): 263.1092

AlogP: 1.86

#Rotatable Bonds: 4

Polar Surface Area: 72.03

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.18

CX LogP: 2.40

CX LogD: 2.38

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.88

Np Likeness Score: -0.35

References

1. Thomas AA, De Meese J, Le Huerou Y, Boyd SA, Romoff TT, Gonzales SS, Gunawardana I, Kaplan T, Sullivan F, Condroski K, Lyssikatos JP, Aicher TD, Ballard J, Bernat B, DeWolf W, Han M, Lemieux C, Smith D, Weiler S, Wright SK, Vigers G, Brandhuber B..  (2008)  Non-charged thiamine analogs as inhibitors of enzyme transketolase.,  18  (2): [PMID:18182286] [10.1016/j.bmcl.2007.11.098]

2. Zhao H, de Carvalho LP, Nathan C, Ouerfelli O..  (2010)  A protecting group-free synthesis of deazathiamine: a step toward inhibitor design.,  20  (22): [PMID:20943392] [10.1016/j.bmcl.2010.09.053]

3. Masini T, Hirsch AK..  (2014)  Development of inhibitors of the 2C-methyl-D-erythritol 4-phosphate (MEP) pathway enzymes as potential anti-infective agents.,  57  (23): [PMID:25210872] [10.1021/jm5010978]

4. Monjas L, Swier LJYM, de Voogd AR, Oudshoorn RC, Hirsch AKH, Slotboom DJ.  (2016)  Design and synthesis of thiamine analogues to study their binding to the ECF transporter for thiamine in bacteria,  7  (5): [10.1039/C6MD00022C]

5. Swier LJYM, Monjas L, Reeßing F, Oudshoorn RC, Aisyah, Primke T, Bakker MM, van Olst E, Ritschel T, Faustino I, Marrink SJ, Hirsch AKH, Slotboom DJ..  (2017)  Insight into the complete substrate-binding pocket of ThiT by chemical and genetic mutations.,  8  (5): [PMID:30108823] [10.1039/C7MD00079K]

Source

Source(1):

• Scientific Literature