4-(3-(4-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)methyl)-1H-1,2,3-triazol-1-yl)propylamino)-2,7-bis(3-(dimethylamino)propyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone

ID: ALA4527280

PubChem CID: 155544779

Max Phase: Preclinical

Molecular Formula: C42H58N8O15

Molecular Weight: 914.97

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)CCCN1C(=O)c2ccc3c4c(c(NCCCn5cc(CO[C@@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)nn5)cc(c24)C1=O)C(=O)N(CCCN(C)C)C3=O

Standard InChI:  InChI=1S/C42H58N8O15/c1-46(2)11-6-14-49-37(58)22-8-9-23-29-28(22)24(39(49)60)16-25(30(29)40(61)50(38(23)59)15-7-12-47(3)4)43-10-5-13-48-17-21(44-45-48)20-62-41-35(57)33(55)36(27(19-52)64-41)65-42-34(56)32(54)31(53)26(18-51)63-42/h8-9,16-17,26-27,31-36,41-43,51-57H,5-7,10-15,18-20H2,1-4H3/t26-,27-,31-,32+,33-,34-,35-,36-,41-,42-/m1/s1

Standard InChI Key:  CCIJNOMNQVUOGJ-JBVNVQTASA-N

Molfile:  

 
     RDKit          2D

 66 72  0  0  0  0  0  0  0  0999 V2000
    2.7559   -3.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0496   -4.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549   -5.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -5.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -5.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -4.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3487   -5.4397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7505   -2.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0402   -2.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -3.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -6.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735   -5.4315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810   -5.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5866   -5.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2919   -5.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2956   -4.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5877   -3.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8762   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6739   -5.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5849   -6.2492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0045   -3.8025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -3.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1673   -2.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9983   -5.4373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3679   -3.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9684   -4.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4473   -6.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8429   -5.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1513   -4.6897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1829   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6040   -4.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4151   -4.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8113   -3.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3902   -3.2198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5729   -3.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6284   -3.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1501   -2.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7862   -2.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6032   -2.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9992   -1.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8162   -1.7610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2122   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2374   -2.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6286   -6.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2102   -5.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4001   -5.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0024   -6.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4208   -6.7855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2370   -6.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1853   -6.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6577   -7.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0228   -7.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2057   -7.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8076   -8.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9905   -8.2371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5924   -8.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5715   -7.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7206   -3.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9038   -4.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4740   -3.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6572   -3.3475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7141   -4.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4199   -3.7962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2007   -4.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1533   -2.7037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3854   -2.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  1
  1  8  1  1
  8  9  1  0
  2 10  1  6
  4 11  1  6
  5 12  1  6
 12 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  1
 14 20  1  1
 16 21  1  1
 18 22  1  1
 22 23  1  0
 15 24  1  6
 25 26  2  0
 26 46  1  0
 30 25  1  0
 31 45  1  0
 44 27  2  0
 27 28  1  0
 28 32  2  0
 26 29  1  0
 30 31  2  0
 30 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  2  0
 35 37  2  0
 34 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 41 43  1  0
 44 45  1  0
 44 49  1  0
 45 46  2  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 47 50  2  0
 49 51  2  0
 48 52  1  0
 52 53  1  0
 53 54  1  0
 54 55  1  0
 55 56  1  0
 55 57  1  0
 58 29  1  0
 58 59  1  0
 59 60  1  0
 60 61  1  0
 21 62  1  0
 62 63  1  0
 63 64  2  0
 64 61  1  0
 61 65  1  0
 65 66  2  0
 66 63  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527280

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 914.97

Molecular Weight (Monoisotopic): 914.4022

AlogP: -2.83

#Rotatable Bonds: 20

Polar Surface Area: 302.51

Molecular Species: BASE

HBA: 21

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 23

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.94

CX Basic pKa: 9.60

CX LogP: -3.19

CX LogD: -6.97

Aromatic Rings: 3

Heavy Atoms: 65

QED Weighted: 0.04

Np Likeness Score: 0.08

References

1. Zuffo M, Stucchi A, Campos-Salinas J, Cabello-Donayre M, Martínez-García M, Belmonte-Reche E, Pérez-Victoria JM, Mergny JL, Freccero M, Morales JC, Doria F..  (2019)  Carbohydrate-naphthalene diimide conjugates as potential antiparasitic drugs: Synthesis, evaluation and structure-activity studies.,  163  [PMID:30503943] [10.1016/j.ejmech.2018.11.043]

Source

Source(1):

• Scientific Literature