3-bromo-7-(5-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)pentyloxy)-4-methyl-2H-chromen-2-one

ID: ALA4474108

PubChem CID: 155536529

Max Phase: Preclinical

Molecular Formula: C26H30BrNO5

Molecular Weight: 516.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)CN(CCCCCOc1ccc3c(C)c(Br)c(=O)oc3c1)CC2

Standard InChI:  InChI=1S/C26H30BrNO5/c1-17-21-8-7-20(15-22(21)33-26(29)25(17)27)32-12-6-4-5-10-28-11-9-18-13-23(30-2)24(31-3)14-19(18)16-28/h7-8,13-15H,4-6,9-12,16H2,1-3H3

Standard InChI Key:  SVZFJRJPPXMZOB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    3.0237  -12.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226  -13.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7306  -13.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7289  -12.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375  -12.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363  -13.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1425  -13.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8544  -13.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8555  -12.7476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448  -12.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5642  -12.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2710  -12.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9797  -12.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159  -12.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083  -12.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3146  -13.9768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072  -13.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6864  -12.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3951  -12.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1018  -12.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8115  -12.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5165  -12.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5194  -11.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8131  -11.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2301  -11.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2217  -12.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9195  -12.7711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6302  -12.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6386  -11.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9363  -11.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3331  -12.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3509  -11.1575    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.9436  -10.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
  1 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 26  1  0
 25 23  1  0
 23 24  2  0
 24 21  1  0
 25 26  2  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 28 31  2  0
 29 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474108

   ---

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: 516.43

Molecular Weight (Monoisotopic): 515.1307

AlogP: 5.49

#Rotatable Bonds: 9

Polar Surface Area: 61.14

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.19

CX LogP: 5.24

CX LogD: 4.39

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: -0.36

References

1. Rullo M, Niso M, Pisani L, Carrieri A, Colabufo NA, Cellamare S, Altomare CD..  (2019)  1,2,3,4-Tetrahydroisoquinoline/2H-chromen-2-one conjugates as nanomolar P-glycoprotein inhibitors: Molecular determinants for affinity and selectivity over multidrug resistance associated protein 1.,  161  [PMID:30384046] [10.1016/j.ejmech.2018.10.043]

Source

Source(1):

• Scientific Literature