6-tert-Butylsulfanylmethyl-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: ALA420159

Max Phase: Preclinical

Molecular Formula: C26H32N2O8S

Molecular Weight: 532.62

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

Standard InChI:  InChI=1S/C26H32N2O8S/c1-25(2,3)37-9-11-10-7-6-8-12(29)13(10)19(30)15-14(11)20(31)17-18(28(4)5)21(32)16(24(27)35)23(34)26(17,36)22(15)33/h6-8,11,14,17-18,20,29-31,34,36H,9H2,1-5H3,(H2,27,35)/t11-,14?,17?,18-,20-,26-/m0/s1

Standard InChI Key:  JZEGWEVJSMZTCF-RJRXTTTASA-N

Molfile:  

     RDKit          2D

 37 40  0  0  1  0  0  0  0  0999 V2000
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    9.9042   -5.1500    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
    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
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    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
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  2  5  1  0
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 14 13  1  0
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 13 16  1  6
 10 17  1  6
 18  6  1  0
 19  8  1  0
 20 11  2  0
 21 16  1  0
  1 22  1  6
 23 15  2  0
 24  5  2  0
 25  7  2  0
 26 21  1  0
 12 27  1  6
 28 15  1  0
 29 14  2  0
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 31 29  1  0
 32 20  1  0
 33 17  1  0
 34 17  1  0
 35 26  1  0
 36 26  1  0
 37 26  1  0
  9 12  1  0
  7 10  1  0
 11 14  1  0
 32 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA420159

   ---

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: 532.62

Molecular Weight (Monoisotopic): 532.1879

AlogP: 1.01

#Rotatable Bonds: 4

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: 2.48

CX Basic pKa: 6.34

CX LogP: -2.65

CX LogD: -4.83

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.31

Np Likeness Score: 0.91

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