6-(3-Chloro-propylsulfanylmethyl)-4-dimethylamino-3,5,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

ID: ALA421456

Max Phase: Preclinical

Molecular Formula: C25H29ClN2O8S

Molecular Weight: 553.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)[C@@H]1C(=O)C(C(N)=O)=C(O)[C@@]2(O)C(=O)C3=C(O)c4c(O)cccc4[C@H](CSCCCCl)C3[C@H](O)C12

Standard InChI:  InChI=1S/C25H29ClN2O8S/c1-28(2)18-17-20(31)14-11(9-37-8-4-7-26)10-5-3-6-12(29)13(10)19(30)15(14)22(33)25(17,36)23(34)16(21(18)32)24(27)35/h3,5-6,11,14,17-18,20,29-31,34,36H,4,7-9H2,1-2H3,(H2,27,35)/t11-,14?,17?,18-,20-,25-/m0/s1

Standard InChI Key:  IUJWLJFAPCFVGG-BPCIZGIYSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  1  0  0  0  0  0999 V2000
    8.2167   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -6.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6417   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6542   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9417   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -6.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3542   -6.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9500   -4.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167   -7.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -7.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2125   -7.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3500   -7.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -7.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3667   -5.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -4.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0750   -6.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -3.8167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -7.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -3.8167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  1  0
  4  6  2  0
  5  1  1  0
  6  1  1  0
  7  4  1  0
  8  2  2  0
  9  2  1  0
 10  3  1  0
 11  8  1  0
 12  3  1  0
 13 14  1  0
 14  9  1  0
 15  4  1  0
 10 16  1  6
 17  6  1  0
 18  8  1  0
 19 11  2  0
  1 20  1  6
 21 15  2  0
 22  5  2  0
 23  7  2  0
 12 24  1  6
 25 15  1  0
 14 26  1  6
 27 13  2  0
 28 26  1  0
 29 19  1  0
 30 37  1  0
 31 36  1  0
 32 27  1  0
 33 19  1  0
 34 16  1  0
 35 16  1  0
 36 28  1  0
 37 31  1  0
  9 12  1  0
  7 10  1  0
 11 13  1  0
 33 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA421456

   ---

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: 553.03

Molecular Weight (Monoisotopic): 552.1333

AlogP: 0.84

#Rotatable Bonds: 7

Polar Surface Area: 181.62

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.56

CX Basic pKa: 6.20

CX LogP: -2.76

CX LogD: -5.13

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.16

Np Likeness Score: 0.97

References

1. Nelson ML, Park BH, Andrews JS, Georgian VA, Thomas RC, Levy SB..  (1993)  Inhibition of the tetracycline efflux antiport protein by 13-thio-substituted 5-hydroxy-6-deoxytetracyclines.,  36  (3): [PMID:8426364] [10.1021/jm00055a008]

2. Chu DT, Plattner JJ, Katz L..  (1996)  New directions in antibacterial research.,  39  (20): [PMID:8831751] [10.1021/jm960294s]

Source

Source(1):

• Scientific Literature