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

ID: ALA2419635

PubChem CID: 73350752

Max Phase: Preclinical

Molecular Formula: C30H38N4O14

Molecular Weight: 678.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CON(CC(=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)C1OC[C@@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C30H38N4O14/c1-9-10-5-6-11(32-13(36)7-34(47-4)29-25(42)21(38)12(35)8-48-29)20(37)15(10)22(39)16-14(9)23(40)18-19(33(2)3)24(41)17(28(31)45)27(44)30(18,46)26(16)43/h5-6,9,12,14,18-19,21,23,25,29,35,37-38,40-43,46H,7-8H2,1-4H3,(H2,31,45)(H,32,36)/t9-,12+,14+,18+,19-,21+,23-,25-,29?,30-/m0/s1

Standard InChI Key:  ORSHVJKTRLRIAW-JEQHZVMPSA-N

Molfile:  

     RDKit          2D

 50 54  0  0  0  0  0  0  0  0999 V2000
   12.7399  -24.0347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0275  -24.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0275  -25.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7399  -25.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3151  -25.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3151  -26.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6068  -25.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8943  -25.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6068  -24.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3151  -24.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8705  -24.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4358  -24.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2928  -24.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1573  -24.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5713  -24.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8747  -23.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2969  -23.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7308  -24.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4482  -23.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0094  -24.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7308  -22.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0176  -23.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5838  -22.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1614  -22.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0060  -24.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5672  -25.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7226  -25.2694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5961  -21.9729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2961  -24.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8622  -24.8589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9977  -25.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1490  -25.2694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0185  -22.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7234  -24.0586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2961  -22.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3045  -25.2694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5829  -23.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5829  -24.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3094  -21.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8871  -21.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7723  -23.5859    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.8747  -22.3875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8722  -24.4447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7298  -21.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1668  -21.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1609  -24.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4501  -24.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1604  -23.2137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7382  -23.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0270  -22.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  1
  3  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
  2 10  1  0
  1  2  1  0
 12 14  2  0
 13 15  1  0
 14 11  1  0
 15 11  1  0
 16 11  1  0
 17 23  1  0
 18 12  1  0
 19 24  1  0
 20 18  1  0
 21 19  1  0
 22 21  1  0
 23 16  1  0
 24 16  1  0
 25 13  1  0
 26 15  2  0
 27 18  2  0
 23 28  1  6
 29 20  1  0
 11 30  1  6
 31 25  2  0
 32 14  1  0
 33 17  1  0
 34 25  1  0
 35 22  1  0
 36 29  1  0
 37 35  2  0
 38 29  2  0
 39 28  1  0
 40 28  1  0
 19 41  1  6
 16 42  1  6
 19 12  1  0
 13 17  2  0
 22 20  2  0
 37 38  1  0
 38 43  1  0
 21 44  1  6
 24 45  1  6
 43 46  1  0
 46 47  1  0
 46 48  2  0
 47  1  1  0
  1 49  1  0
 49 50  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2419635

   (4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-9-[[2-[methoxy-[(3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]amino]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: 678.65

Molecular Weight (Monoisotopic): 678.2385

AlogP: -3.11

#Rotatable Bonds: 7

Polar Surface Area: 293.11

Molecular Species: ACID

HBA: 16

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.87

CX Basic pKa: 7.78

CX LogP: -6.34

CX LogD: -6.84

Aromatic Rings: 1

Heavy Atoms: 48

QED Weighted: 0.08

Np Likeness Score: 1.12

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