1-(((3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)-3-(((3S,5aR,6S,8aR,9S,12R,12aS)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)propan-2-ol

ID: ALA5287969

Max Phase: Preclinical

Molecular Formula: C33H52O11

Molecular Weight: 624.77

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC[C@H]2[C@@H](C)C(OCC(O)COC3O[C@@H]4O[C@]5(C)CC[C@@H]6[C@@H](C)CC[C@H]([C@@H]3C)[C@]46OO5)O[C@H]3O[C@@]4(C)CC[C@@H]1[C@]32OO4

Standard InChI:  InChI=1S/C33H52O11/c1-17-7-9-24-19(3)26(37-28-32(24)22(17)11-13-30(5,39-28)41-43-32)35-15-21(34)16-36-27-20(4)25-10-8-18(2)23-12-14-31(6)40-29(38-27)33(23,25)44-42-31/h17-29,34H,7-16H2,1-6H3/t17-,18+,19-,20+,21?,22+,23-,24+,25-,26?,27?,28+,29-,30-,31+,32-,33+

Standard InChI Key:  OWMLCUDUBMKZIQ-NWBCVEIVSA-N

Molfile:  

 
     RDKit          2D

 50 57  0  0  0  0  0  0  0  0999 V2000
   -2.7986    3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    2.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1675    2.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224    1.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6492    0.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7408    1.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4267    2.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -0.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -1.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -1.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -2.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -2.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329   -2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578   -1.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    0.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1705    0.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0058    1.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6492    2.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571    1.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9084    2.0852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365    0.7957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7956    1.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3718    3.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578    3.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7133    2.8535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0274    2.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0822    0.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6310    1.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444    0.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444   -0.0823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578    1.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7712    0.7408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7712   -0.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705   -2.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705   -1.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -3.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1675   -3.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444   -3.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2347   -1.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578   -0.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993   -0.8231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462   -2.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3322   -2.3321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1097   -2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -3.3748    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705   -0.9054    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705   -0.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224    0.4389    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571    3.1004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5120    3.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  6  7  1  0
  7  3  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  0
 12 11  1  0
 10 14  1  0
  4 15  1  0
 15  5  1  0
  5 16  1  6
  5 17  1  0
 17 18  1  0
 18  2  1  0
  5 19  1  0
 19 20  1  0
  3 20  1  6
  4 21  1  0
 21 22  1  0
 22  6  1  0
  7 23  1  0
 23 24  1  0
 24  1  1  0
  7 25  1  6
  6 26  1  1
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33  8  1  0
 34 12  1  0
 35 34  1  0
  9 35  1  0
 12 36  1  6
 37 11  1  0
 38 37  1  0
 13 38  1  0
 39 13  1  0
 14 39  1  0
 14 40  1  0
 40 33  1  0
 14 41  1  6
 13 42  1  0
 42 43  1  0
 10 43  1  6
 13 44  1  6
 11 45  1  6
  9 46  1  6
  8 47  1  1
  4 48  1  6
  2 49  1  6
  1 50  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5287969

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 624.77

Molecular Weight (Monoisotopic): 624.3510

AlogP: 4.80

#Rotatable Bonds: 6

Polar Surface Area: 112.53

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.67

CX Basic pKa: ┄

CX LogP: 6.16

CX LogD: 6.16

Aromatic Rings: ┄

Heavy Atoms: 44

QED Weighted: 0.41

Np Likeness Score: 1.82

References

1. Fröhlich T, Çapcı Karagöz A, Reiter C, Tsogoeva SB..  (2016)  Artemisinin-Derived Dimers: Potent Antimalarial and Anticancer Agents.,  59  (16): [PMID:27010926] [10.1021/acs.jmedchem.5b01380]

Source

Source(1):

• Scientific Literature