4-methyl-7-(3-(4-((((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)propoxy)-2H-chromen-2-one

ID: ALA5285620

Max Phase: Preclinical

Molecular Formula: C31H39N3O8

Molecular Weight: 581.67

Names and Identifiers

Canonical SMILES:  Cc1cc(=O)oc2cc(OCCCn3cc(CO[C@H]4O[C@@H]5O[C@@]6(C)CC[C@H]7[C@H](C)CC[C@@H]([C@H]4C)[C@@]57OO6)nn3)ccc12

Standard InChI:  InChI=1S/C31H39N3O8/c1-18-6-9-25-20(3)28(39-29-31(25)24(18)10-11-30(4,40-29)41-42-31)37-17-21-16-34(33-32-21)12-5-13-36-22-7-8-23-19(2)14-27(35)38-26(23)15-22/h7-8,14-16,18,20,24-25,28-29H,5-6,9-13,17H2,1-4H3/t18-,20-,24+,25+,28+,29-,30-,31-/m1/s1

Standard InChI Key:  DTECIBBZWUIRES-JOFFVHFSSA-N

Molfile:  

 
     RDKit          2D

 45 51  0  0  0  0  0  0  0  0999 V2000
   -0.1868    0.6216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254    1.3361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264    1.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801    1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9938    0.7932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7949    2.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5097    1.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245    2.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392    1.6140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6540    2.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6540    1.2010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6540    2.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687    3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1659    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4683    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0559    1.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1769    0.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9460    2.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3962    2.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2313    1.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0254    3.7633    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687    4.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0835    4.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6540    4.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392    4.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392    3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245    3.6761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2245    2.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5097    3.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509    1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636    0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2890    0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7017    1.3361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270    1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7629    2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1757    1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665    0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9415    0.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1804   -0.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012   -0.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4068    0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9945    1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4072    2.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4138   -0.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  3  4  2  0
  5  4  1  0
  1  5  2  0
  6  4  1  0
  7  6  1  0
  8  7  1  1
  9  8  1  0
 10  9  1  0
 10 11  1  1
 12 10  1  0
 13 12  1  0
 14 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  6
 18 19  1  0
 12 19  1  6
 16 20  1  0
 10 20  1  0
 13 21  1  6
 13 22  1  0
 22 23  1  6
 24 22  1  0
 25 24  1  0
 26 25  1  0
 12 26  1  0
 26 27  1  6
 28 26  1  0
  8 28  1  0
 28 29  1  1
  2 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 35 34  2  0
 36 35  1  0
 37 36  2  0
 38 37  1  0
 39 38  2  0
 34 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  2  0
 37 43  1  0
 43 44  1  0
 41 45  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285620

   ---

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: 581.67

Molecular Weight (Monoisotopic): 581.2737

AlogP: 4.89

#Rotatable Bonds: 8

Polar Surface Area: 116.30

Molecular Species: NEUTRAL

HBA: 11

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.15

CX LogD: 5.15

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.21

Np Likeness Score: 1.11

References

1. Gao F, Sun Z, Kong F, Xiao J..  (2020)  Artemisinin-derived hybrids and their anticancer activity.,  188  [PMID:31945642] [10.1016/j.ejmech.2020.112044]

Source

Source(1):

• Scientific Literature