6-(2,3-Dihydroxy-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: ALA338852

Max Phase: Preclinical

Molecular Formula: C25H30N2O10S

Molecular Weight: 550.59

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](CSCC(O)CO)C3[C@H](O)C12

Standard InChI:  InChI=1S/C25H30N2O10S/c1-27(2)18-17-20(32)14-11(8-38-7-9(29)6-28)10-4-3-5-12(30)13(10)19(31)15(14)22(34)25(17,37)23(35)16(21(18)33)24(26)36/h3-5,9,11,14,17-18,20,28-32,35,37H,6-8H2,1-2H3,(H2,26,36)/t9?,11-,14?,17?,18-,20-,25-/m0/s1

Standard InChI Key:  CIDMBMACWOWJQY-UPSYKXGESA-N

Molfile:  

     RDKit          2D

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   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
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   11.0750   -6.3292    0.0000 N   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
    6.0792   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2250   -2.5792    0.0000 O   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
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    3.9417   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  5  1  0
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  4  6  2  0
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  7  4  1  0
  8  2  2  0
  9  2  1  0
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 13 14  1  0
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 15  4  1  0
 10 16  1  6
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 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
 26 27  1  0
 14 27  1  6
 28 13  2  0
 29 33  1  0
 30 19  1  0
 31 29  1  0
 32 38  1  0
 33 26  1  0
 34 28  1  0
 35 19  1  0
 36 16  1  0
 37 16  1  0
 38 29  1  0
  9 12  1  0
  7 10  1  0
 11 13  1  0
 35 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA338852

   ---

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: 550.59

Molecular Weight (Monoisotopic): 550.1621

AlogP: -1.44

#Rotatable Bonds: 7

Polar Surface Area: 222.08

Molecular Species: ACID

HBA: 12

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.56

CX Basic pKa: 6.22

CX LogP: -4.96

CX LogD: -7.28

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.18

Np Likeness Score: 1.19

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