(4S,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)-9-(Nmethoxyglycyl)amino-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

ID: ALA2419637

PubChem CID: 73349174

Max Phase: Preclinical

Molecular Formula: C25H30N4O10

Molecular Weight: 546.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CONCC(=O)Nc1ccc2c(c1O)C(=O)C1=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]3[C@@H](O)[C@@H]1[C@H]2C

Standard InChI:  InChI=1S/C25H30N4O10/c1-8-9-5-6-10(28-11(30)7-27-39-4)18(31)13(9)19(32)14-12(8)20(33)16-17(29(2)3)21(34)15(24(26)37)23(36)25(16,38)22(14)35/h5-6,8,12,16-17,20,27,31,33-35,38H,7H2,1-4H3,(H2,26,37)(H,28,30)/t8-,12+,16+,17-,20-,25-/m0/s1

Standard InChI Key:  BJYZLQVUQXVZRN-XPEKFKQWSA-N

Molfile:  

     RDKit          2D

 41 44  0  0  0  0  0  0  0  0999 V2000
   12.8522   -7.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4242   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2678   -7.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1423   -8.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5497   -8.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8563   -6.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2720   -6.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7225   -8.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4366   -6.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0044   -7.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7225   -6.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0127   -6.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5621   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1464   -6.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9777   -8.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5456   -8.9932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7143   -8.9891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5745   -5.7080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2945   -8.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8439   -8.5805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9695   -9.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1341   -8.9891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9901   -6.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6917   -7.7840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2945   -6.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3028   -8.9891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5846   -6.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5846   -7.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2843   -5.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8687   -5.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7638   -7.3134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8563   -6.1207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8772   -8.1683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1692   -7.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4618   -8.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1687   -6.9429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7538   -7.7611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0464   -8.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3384   -7.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7215   -5.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1517   -5.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  2  0
  3  5  1  0
  4  1  1  0
  5  1  1  0
  6  1  1  0
  7 13  1  0
  8  2  1  0
  9 14  1  0
 10  8  1  0
 11  9  1  0
 12 11  1  0
 13  6  1  0
 14  6  1  0
 15  3  1  0
 16  5  2  0
 17  8  2  0
 13 18  1  6
 19 10  1  0
  1 20  1  6
 21 15  2  0
 22  4  1  0
 23  7  1  0
 24 15  1  0
 25 12  1  0
 26 19  1  0
 27 25  2  0
 28 19  2  0
 29 18  1  0
 30 18  1  0
  9 31  1  6
  6 32  1  6
  9  2  1  0
  3  7  2  0
 12 10  2  0
 27 28  1  0
 28 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 35 37  1  0
 37 38  1  0
 38 39  1  0
 11 40  1  6
 14 41  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2419637

   (4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-9-[[2-(methoxyamino)acetyl]amino]-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide

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: 546.53

Molecular Weight (Monoisotopic): 546.1962

AlogP: -1.26

#Rotatable Bonds: 6

Polar Surface Area: 231.98

Molecular Species: ACID

HBA: 12

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.75

CX Basic pKa: 7.78

CX LogP: -4.51

CX LogD: -5.00

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.12

Np Likeness Score: 1.36

References

1. Zhang J, Ponomareva LV, Marchillo K, Zhou M, Andes DR, Thorson JS..  (2013)  Synthesis and antibacterial activity of doxycycline neoglycosides.,  76  (9): [PMID:23987662] [10.1021/np4003096]

Source

Source(1):

• Scientific Literature