(1R,3S,6R)-4,6-Diamino-2-[2-(3-amino-propylamino)-ethoxy]-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexanol

ID: ALA371500

PubChem CID: 44404593

Max Phase: Preclinical

Molecular Formula: C22H32F3N5O3S

Molecular Weight: 503.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCNCCOC1[C@@H](OCSc2ccnc3cc(C(F)(F)F)ccc23)C(N)C[C@@H](N)[C@H]1O

Standard InChI:  InChI=1S/C22H32F3N5O3S/c23-22(24,25)13-2-3-14-17(10-13)30-7-4-18(14)34-12-33-20-16(28)11-15(27)19(31)21(20)32-9-8-29-6-1-5-26/h2-4,7,10,15-16,19-21,29,31H,1,5-6,8-9,11-12,26-28H2/t15-,16?,19-,20+,21?/m1/s1

Standard InChI Key:  WYNYJAPRXMNOGA-ZNSMGHQKSA-N

Molfile:  

     RDKit          2D

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  5 23  1  1
 24  6  1  0
  2 25  1  6
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 27 14  2  0
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 29 32  1  0
 30 31  1  0
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 32 30  1  0
 33 34  1  0
 34 22  1  0
  5  8  1  0
 13  9  1  0
 11 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA371500

   (1R,3S,6R)-4,6-diamino-2-[2-(3-aminopropylamino)ethoxy]-3-[[7-(trifluoromethyl)quinolin-4-yl]sulfanylmethoxy]cyclohexan-1-ol

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: 503.59

Molecular Weight (Monoisotopic): 503.2178

AlogP: 1.43

#Rotatable Bonds: 11

Polar Surface Area: 141.67

Molecular Species: BASE

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.53

CX Basic pKa: 10.17

CX LogP: -0.01

CX LogD: -6.06

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.17

Np Likeness Score: -0.21

References

1. Wang X, Migawa MT, Sannes-Lowery KA, Swayze EE..  (2005)  The synthesis and 16S A-site rRNA recognition of carbohydrate-free aminoglycosides.,  15  (22): [PMID:16168642] [10.1016/j.bmcl.2005.08.027]

Source

Source(1):

• Scientific Literature