ID: ALA2086581

Max Phase: Preclinical

Molecular Formula: C35H42N8O4

Molecular Weight: 638.77

Molecule Type: Small molecule

Representations

Canonical SMILES:  C=C[C@]1(C)C[C@@H](OC(=O)Cn2cc(-c3ccc(-n4cnc5c(N)ncnc54)cc3)nn2)[C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@H]32)[C@@H](C)[C@@H]1O

Standard InChI:  InChI=1S/C35H42N8O4/c1-6-33(4)15-26(34(5)20(2)11-13-35(21(3)30(33)46)14-12-25(44)29(34)35)47-27(45)17-42-16-24(40-41-42)22-7-9-23(10-8-22)43-19-39-28-31(36)37-18-38-32(28)43/h6-10,16,18-21,26,29-30,46H,1,11-15,17H2,2-5H3,(H2,36,37,38)/t20-,21+,26-,29+,30+,33-,34+,35+/m1/s1

Standard InChI Key:  QZUTTXSQDMFTQC-OPQGOLPDSA-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: 638.77

Molecular Weight (Monoisotopic): 638.3329

AlogP: 4.56

#Rotatable Bonds: 6

Polar Surface Area: 163.93

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 4.35

CX LogP: 4.55

CX LogD: 4.55

Aromatic Rings: 4

Heavy Atoms: 47

QED Weighted: 0.23

Np Likeness Score: 0.58

References

1. Dreier I, Kumar S, Søndergaard H, Rasmussen ML, Hansen LH, List NH, Kongsted J, Vester B, Nielsen P..  (2012)  A click chemistry approach to pleuromutilin derivatives, part 2: conjugates with acyclic nucleosides and their ribosomal binding and antibacterial activity.,  55  (5): [PMID:22280300] [10.1021/jm201266b]

2. Dreier I, Hansen LH, Nielsen P, Vester B..  (2014)  A click chemistry approach to pleuromutilin derivatives. Part 3: extended footprinting analysis and excellent MRSA inhibition for a derivative with an adenine phenyl side chain.,  24  (4): [PMID:24486133] [10.1016/j.bmcl.2014.01.019]

3. Heidtmann CV,Voukia F,Hansen LN,Sørensen SH,Urlund B,Nielsen S,Pedersen M,Kelawi N,Andersen BN,Pedersen M,Reinholdt P,Kongsted J,Nielsen CU,Klitgaard JK,Nielsen P.  (2020)  Discovery of a Potent Adenine-Benzyltriazolo-Pleuromutilin Conjugate with Pronounced Antibacterial Activity against MRSA.,  63  (24): [PMID:33325700] [10.1021/acs.jmedchem.0c01328]

Source

Source(1):

• Scientific Literature