3-(9-Carbamoyl-7-dimethylamino-1,6,8,10a,11-pentahydroxy-10,12-dioxo-5,5a,6,6a,7,10,10a,12-octahydro-naphthacen-5-ylmethylsulfanyl)-propionic acid

ID: ALA332172

Max Phase: Preclinical

Molecular Formula: C25H28N2O10S

Molecular Weight: 548.57

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](CSCCC(=O)O)C3[C@H](O)C12

Standard InChI:  InChI=1S/C25H28N2O10S/c1-27(2)18-17-20(32)14-10(8-38-7-6-12(29)30)9-4-3-5-11(28)13(9)19(31)15(14)22(34)25(17,37)23(35)16(21(18)33)24(26)36/h3-5,10,14,17-18,20,28,31-32,35,37H,6-8H2,1-2H3,(H2,26,36)(H,29,30)/t10-,14?,17?,18-,20-,25-/m0/s1

Standard InChI Key:  FHHSWCLOBHNGIS-XBEAGTRSSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  1  0  0  0  0  0999 V2000
    8.2167   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -6.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6417   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6542   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9417   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -6.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   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
    8.9167   -7.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -7.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2125   -7.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3500   -7.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -7.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3667   -5.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -5.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -4.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0750   -6.3292    0.0000 N   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
    4.6542   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -3.8167    0.0000 O   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
    4.6542   -7.5417    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
    3.9417   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667   -3.8417    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 14  1  0
 14  9  1  0
 15  4  1  0
 10 16  1  6
 17  6  1  0
 18 25  1  0
 19  8  1  0
 20 11  2  0
  1 21  1  6
 22 15  2  0
 23  5  2  0
 24  7  2  0
 25 34  1  0
 26 18  2  0
 12 27  1  6
 28 15  1  0
 14 29  1  6
 30 13  2  0
 31 18  1  0
 32 29  1  0
 33 20  1  0
 34 32  1  0
 35 30  1  0
 36 20  1  0
 37 16  1  0
 38 16  1  0
  9 12  1  0
  7 10  1  0
 11 13  1  0
 36 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA332172

   ---

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: 548.57

Molecular Weight (Monoisotopic): 548.1465

AlogP: -0.32

#Rotatable Bonds: 7

Polar Surface Area: 218.92

Molecular Species: ACID

HBA: 11

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.53

CX Basic pKa: 6.23

CX LogP: -3.95

CX LogD: -9.45

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.17

Np Likeness Score: 0.99

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