6-Cyclohexylsulfanylmethyl-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: ALA339999

Max Phase: Preclinical

Molecular Formula: C28H34N2O8S

Molecular Weight: 558.65

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](CSC4CCCCC4)C3[C@H](O)C12

Standard InChI:  InChI=1S/C28H34N2O8S/c1-30(2)21-20-23(33)17-14(11-39-12-7-4-3-5-8-12)13-9-6-10-15(31)16(13)22(32)18(17)25(35)28(20,38)26(36)19(24(21)34)27(29)37/h6,9-10,12,14,17,20-21,23,31-33,36,38H,3-5,7-8,11H2,1-2H3,(H2,29,37)/t14-,17?,20?,21-,23-,28-/m0/s1

Standard InChI Key:  HYCVENHJHWGJDJ-SMHFBFMPSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  1  0  0  0  0  0999 V2000
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    6.3292   -6.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    4.9042   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6167   -4.2917    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
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    7.7500   -7.1875    0.0000 O   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
    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
    4.1875   -5.1250    0.0000 C   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
    4.1042   -4.0917    0.0000 C   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
    9.2000   -3.9042    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
    3.5167   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -5.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -4.5042    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  9  1  0
 14 13  1  0
 15  4  1  0
 13 16  1  6
 10 17  1  6
 18  6  1  0
 19  8  1  0
 20 11  2  0
  1 21  1  6
 22 16  1  0
 23 15  2  0
 24  5  2  0
 25  7  2  0
 12 26  1  6
 27 15  1  0
 28 14  2  0
 29 20  1  0
 30 22  1  0
 31 28  1  0
 32 20  1  0
 33 17  1  0
 34 17  1  0
 35 30  1  0
 36 30  1  0
 37 36  1  0
 38 35  1  0
 39 37  1  0
  9 12  1  0
  7 10  1  0
 11 14  1  0
 32 31  2  0
 39 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA339999

   ---

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: 558.65

Molecular Weight (Monoisotopic): 558.2036

AlogP: 1.54

#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: 2.52

CX Basic pKa: 6.27

CX LogP: -1.79

CX LogD: -4.01

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.29

Np Likeness Score: 0.92

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