6-(4-Chloro-benzylsulfanylmethyl)-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: ALA125115

Max Phase: Preclinical

Molecular Formula: C29H29ClN2O8S

Molecular Weight: 601.08

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](CSCc4ccc(Cl)cc4)C3[C@H](O)C12

Standard InChI:  InChI=1S/C29H29ClN2O8S/c1-32(2)22-21-24(35)18-15(11-41-10-12-6-8-13(30)9-7-12)14-4-3-5-16(33)17(14)23(34)19(18)26(37)29(21,40)27(38)20(25(22)36)28(31)39/h3-9,15,18,21-22,24,33-35,38,40H,10-11H2,1-2H3,(H2,31,39)/t15-,18?,21?,22-,24-,29-/m0/s1

Standard InChI Key:  SHWWESHABXVDFA-RPGGHDGHSA-N

Molfile:  

     RDKit          2D

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    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
    4.9042   -3.8792    0.0000 S   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
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    2.0500   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1917   -7.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -2.6417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4792   -3.0542    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
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    9.2000   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 14  1  0
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 10 16  1  6
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 19 11  2  0
  1 20  1  6
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 22  5  2  0
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 12 24  1  6
 25 15  1  0
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 14 27  1  6
 28 13  2  0
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 30 38  1  0
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 32 29  1  0
 33 35  2  0
 34 36  1  0
 35 30  1  0
 36 30  2  0
 37 28  1  0
 38 26  1  0
 39 19  1  0
 40 16  1  0
 41 16  1  0
  9 12  1  0
  7 10  1  0
 11 13  1  0
 39 37  2  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA125115

   ---

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: 601.08

Molecular Weight (Monoisotopic): 600.1333

AlogP: 2.06

#Rotatable Bonds: 6

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: 2.57

CX Basic pKa: 6.22

CX LogP: -1.15

CX LogD: -3.47

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.27

Np Likeness Score: 0.64

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