4-Dimethylamino-3,5,10,12,12a-pentahydroxy-1,11-dioxo-6-phenylmethanesulfinylmethyl-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

ID: ALA124794

Max Phase: Preclinical

Molecular Formula: C29H30N2O9S

Molecular Weight: 582.63

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](C[S+]([O-])Cc4ccccc4)C3[C@H](O)C12

Standard InChI:  InChI=1S/C29H30N2O9S/c1-31(2)22-21-24(34)18-15(12-41(40)11-13-7-4-3-5-8-13)14-9-6-10-16(32)17(14)23(33)19(18)26(36)29(21,39)27(37)20(25(22)35)28(30)38/h3-10,15,18,21-22,24,32-34,37,39H,11-12H2,1-2H3,(H2,30,38)/t15-,18?,21?,22-,24-,29-,41?/m0/s1

Standard InChI Key:  GCIJODSHNHYEEA-CPOVSRRCSA-N

Molfile:  

     RDKit          2D

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    8.7327   -4.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5805   -4.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4233   -4.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0151   -3.3987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5694   -6.7119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4521   -4.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5772   -3.4002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -3.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1613   -5.4903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7006   -4.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7148   -6.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9788   -2.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855   -4.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9888   -5.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2966   -2.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2679   -3.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9797   -2.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2570   -1.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5452   -3.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5419   -2.1668    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
 16 17  1  0
 13 17  1  6
 10 18  1  6
 19  6  1  0
 20  8  1  0
 21 11  2  0
  1 22  1  6
 23 15  2  0
 24 16  1  0
 25  5  2  0
 26  7  2  0
 12 27  1  6
 28 16  1  0
 29 15  1  0
 30 14  2  0
 31 21  1  0
 32 28  1  0
 33 30  1  0
 34 21  1  0
 35 18  1  0
 36 18  1  0
 37 32  1  0
 38 32  2  0
 39 38  1  0
 40 37  2  0
 41 39  2  0
  9 12  1  0
  7 10  1  0
 11 14  1  0
 34 33  2  0
 41 40  1  0
M  CHG  2  16   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA124794

   ---

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: 582.63

Molecular Weight (Monoisotopic): 582.1672

AlogP: 0.42

#Rotatable Bonds: 6

Polar Surface Area: 204.68

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.40

CX Basic pKa: 5.09

CX LogP: -3.73

CX LogD: -6.41

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.20

Np Likeness Score: 0.98

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