(3aR,4R,7R,9R,10R,11R,13R,15S,15aR,E)-10-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-14-((E)-3-(quinolin-3-yl)allyloxyimino)octahydro-3aH-[1,3]dioxolo[4,5-c][1]oxacyclotetradecine-2,6,8(4H,7H)-trione

ID: ALA2316683

PubChem CID: 46934052

Max Phase: Preclinical

Molecular Formula: C43H61N3O11

Molecular Weight: 795.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(OC)C[C@@H](C)/C(=N\OC/C=C/c2cnc3ccccc3c2)[C@H](C)[C@H]2OC(=O)O[C@@]21C

Standard InChI:  InChI=1S/C43H61N3O11/c1-12-33-43(8)38(56-41(50)57-43)26(4)34(45-52-19-15-16-29-21-30-17-13-14-18-31(30)44-23-29)24(2)22-42(7,51-11)37(27(5)35(47)28(6)39(49)54-33)55-40-36(48)32(46(9)10)20-25(3)53-40/h13-18,21,23-28,32-33,36-38,40,48H,12,19-20,22H2,1-11H3/b16-15+,45-34+/t24-,25-,26+,27+,28-,32+,33-,36-,37-,38-,40+,42-,43-/m1/s1

Standard InChI Key:  GPMSCAIHDUSNFA-JFJRPKKDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2316683

   (1R,2R,5R,7R,8R,9R,11R,12E,13S,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-12-[(E)-3-quinolin-3-ylprop-2-enoxy]imino-3,15,17-trioxabicyclo[12.3.0]heptadecane-4,6,16-trione

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: 795.97

Molecular Weight (Monoisotopic): 795.4306

AlogP: 5.97

#Rotatable Bonds: 9

Polar Surface Area: 164.54

Molecular Species: NEUTRAL

HBA: 14

HBD: 1

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.93

CX Basic pKa: 8.27

CX LogP: 7.03

CX LogD: 6.42

Aromatic Rings: 2

Heavy Atoms: 57

QED Weighted: 0.14

Np Likeness Score: 1.02

References

1. Liang JH, An K, Lv W, Cushman M, Wang H, Xu YC..  (2013)  Synthesis, antibacterial activity and docking of 14-membered 9-O-(3-arylalkyl) oxime 11,12-cyclic carbonate ketolides.,  59  [PMID:23202851] [10.1016/j.ejmech.2012.10.054]

2. Liang JH, Lv W, Li XL, An K, Cushman M, Wang H, Xu YC..  (2013)  Synthesis and antibacterial activity of 9-oxime ether non-ketolides, and novel binding mode of alkylides with bacterial rRNA.,  23  (5): [PMID:23375796] [10.1016/j.bmcl.2012.12.070]

3. Han X, Lv W, Guo SY, Cushman M, Liang JH..  (2015)  Synthesis and structure-activity relationships of novel 9-oxime acylides with improved bactericidal activity.,  23  (19): [PMID:26349628] [10.1016/j.bmc.2015.08.020]

4. Tian JC, Han X, Lv W, Li YX, Wang H, Fan BZ, Cushman M, Liang JH..  (2017)  Design, synthesis and structure-bactericidal activity relationships of novel 9-oxime ketolides and reductive epimers of acylides.,  27  (7): [PMID:28256375] [10.1016/j.bmcl.2017.02.041]

Source

Source(1):

• Scientific Literature