4-Dimethylamino-6-ethylsulfanylmethyl-3,5,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

ID: ALA125490

Max Phase: Preclinical

Molecular Formula: C24H28N2O8S

Molecular Weight: 504.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSC[C@H]1c2cccc(O)c2C(=O)C2=C(O)[C@]3(O)C(O)=C(C(N)=O)C(=O)[C@@H](N(C)C)C3[C@@H](O)C21

Standard InChI:  InChI=1S/C24H28N2O8S/c1-4-35-8-10-9-6-5-7-11(27)12(9)18(28)14-13(10)19(29)16-17(26(2)3)20(30)15(23(25)33)22(32)24(16,34)21(14)31/h5-7,10,13,16-17,19,27,29,31-32,34H,4,8H2,1-3H3,(H2,25,33)/t10-,13?,16?,17-,19-,24-/m0/s1

Standard InChI Key:  UOXCZKZLFAZKJN-DTZWRUDESA-N

Molfile:  

     RDKit          2D

 35 38  0  0  1  0  0  0  0  0999 V2000
    7.7542   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -6.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7625   -5.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1792   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4625   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1875   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4750   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -6.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8917   -6.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -4.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542   -7.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -7.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -6.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7500   -7.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8792   -7.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -7.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042   -5.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -4.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042   -6.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -3.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -7.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2000   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  2  0
  3  1  1  0
  4  6  2  0
  5  1  1  0
  6  1  1  0
  7  4  1  0
  8  2  1  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  2  0
 19 11  2  0
  1 20  1  6
 21 15  2  0
 22  5  1  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 27  1  0
 31 19  1  0
 32 16  1  0
 33 16  1  0
 34 28  1  0
 35 34  1  0
  9 12  1  0
  7 10  1  0
 11 13  1  0
 31 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA125490

   ---

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: 504.56

Molecular Weight (Monoisotopic): 504.1566

AlogP: 0.39

#Rotatable Bonds: 5

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: 2.81

CX Basic pKa: 5.77

CX LogP: -2.84

CX LogD: -3.84

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: 1.07

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]

Source

Source(1):

• Scientific Literature