4alpha-(6-bromopyridine-2-acyl)-4-desoxy-podophyllotoxin

ID: ALA4583480

PubChem CID: 155561738

Max Phase: Preclinical

Molecular Formula: C28H24BrNO9

Molecular Weight: 598.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@H](OC(=O)c3cccc(Br)n3)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

Standard InChI:  InChI=1S/C28H24BrNO9/c1-33-20-7-13(8-21(34-2)26(20)35-3)23-14-9-18-19(38-12-37-18)10-15(14)25(16-11-36-28(32)24(16)23)39-27(31)17-5-4-6-22(29)30-17/h4-10,16,23-25H,11-12H2,1-3H3/t16-,23+,24-,25-/m0/s1

Standard InChI Key:  CCDBRLHAQUXQMV-RGWZMNCVSA-N

Molfile:  

 
     RDKit          2D

 41 46  0  0  0  0  0  0  0  0999 V2000
   30.0864  -17.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0851  -16.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8003  -16.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7993  -17.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5155  -17.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5172  -16.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3718  -17.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3727  -16.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5882  -16.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1005  -17.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5826  -17.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2368  -16.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2344  -17.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0199  -17.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5099  -17.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0279  -16.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5166  -18.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8007  -19.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7996  -20.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5141  -20.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2264  -20.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2249  -19.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5173  -15.4720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8029  -15.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8029  -14.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0884  -15.4720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5142  -21.2488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7997  -21.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9416  -20.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9430  -21.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0847  -20.4229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0837  -21.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2735  -18.5879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2344  -18.3656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.2368  -15.8889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.5221  -13.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5225  -13.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8085  -12.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0927  -13.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0958  -13.8272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3784  -12.5942    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
  1  4  2  0
  3  2  2  0
  2  8  1  0
  3  4  1  0
  3  6  1  0
  4  5  1  0
  5 13  1  0
 12  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  5 17  1  6
  6 23  1  6
 23 24  1  0
 24 25  1  0
 24 26  2  0
 20 27  1  0
 27 28  1  0
 21 29  1  0
 29 30  1  0
 19 31  1  0
 31 32  1  0
 14 33  2  0
 13 34  1  1
 12 35  1  6
 25 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 25  1  0
 39 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4583480

   ---

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: 598.40

Molecular Weight (Monoisotopic): 597.0634

AlogP: 4.43

#Rotatable Bonds: 6

Polar Surface Area: 111.64

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.06

CX LogD: 4.06

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.30

Np Likeness Score: 0.86

References

1. Zhang L, Chen F, Zhang Z, Chen Y, Lin Y, Wang J..  (2016)  Design, synthesis and evaluation of the multidrug resistance-reversing activity of pyridine acid esters of podophyllotoxin in human leukemia cells.,  26  (18): [PMID:27503681] [10.1016/j.bmcl.2016.07.072]

Source

Source(1):

• Scientific Literature