(R)-5-((7-Chloro-10-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-3-methyl-1-oxo-6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)methyl)furan-2-carboxylic Acid

ID: ALA4521315

PubChem CID: 118394699

Max Phase: Preclinical

Molecular Formula: C35H36Cl2N4O5

Molecular Weight: 663.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(OCCCc2c3n(c4c(-c5c(C)nn(C)c5C)c(Cl)ccc24)C[C@@H](C)N(Cc2ccc(C(=O)O)o2)C3=O)cc(C)c1Cl

Standard InChI:  InChI=1S/C35H36Cl2N4O5/c1-18-14-24(15-19(2)31(18)37)45-13-7-8-25-26-10-11-27(36)30(29-21(4)38-39(6)22(29)5)32(26)41-16-20(3)40(34(42)33(25)41)17-23-9-12-28(46-23)35(43)44/h9-12,14-15,20H,7-8,13,16-17H2,1-6H3,(H,43,44)/t20-/m1/s1

Standard InChI Key:  DBLYUECFQBVGCM-HXUWFJFHSA-N

Molfile:  

 
     RDKit          2D

 46 51  0  0  0  0  0  0  0  0999 V2000
    2.6606  -14.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595  -15.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675  -16.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658  -14.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744  -14.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0746  -15.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8533  -15.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528  -14.4124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3602  -13.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198  -13.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650  -12.3388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9477  -12.3412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977  -13.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433  -11.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454  -16.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5491  -17.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5411  -17.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2448  -18.3510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9212  -13.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2369  -19.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237  -19.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5154  -20.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2197  -20.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9337  -20.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9385  -19.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2128  -21.6166    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.6389  -20.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8036  -20.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8529  -14.5641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3340  -15.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1432  -15.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4777  -14.3947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9967  -13.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1811  -13.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7978  -13.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6228  -15.8025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2928  -14.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7040  -15.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3760  -15.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9853  -16.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6916  -15.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5186  -15.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4394  -16.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4348  -17.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1251  -15.8615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3296  -12.9865    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
  6  7  1  0
  7 30  2  0
 29  5  1  0
  1  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
  4  9  1  0
 11 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 24 27  1  0
 22 28  1  0
 29 30  1  0
 29 34  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 10 35  1  0
 31 36  2  0
 32 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 38  1  0
 41 43  1  0
 43 44  2  0
 43 45  1  0
 33 46  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4521315

   US10533010, Example I-123

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: 663.60

Molecular Weight (Monoisotopic): 662.2063

AlogP: 7.93

#Rotatable Bonds: 9

Polar Surface Area: 102.73

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.86

CX Basic pKa: 3.46

CX LogP: 6.40

CX LogD: 3.60

Aromatic Rings: 5

Heavy Atoms: 46

QED Weighted: 0.16

Np Likeness Score: -0.83

References

1. Lee T, Christov PP, Shaw S, Tarr JC, Zhao B, Veerasamy N, Jeon KO, Mills JJ, Bian Z, Sensintaffar JL, Arnold AL, Fogarty SA, Perry E, Ramsey HE, Cook RS, Hollingshead M, Davis Millin M, Lee KM, Koss B, Budhraja A, Opferman JT, Kim K, Arteaga CL, Moore WJ, Olejniczak ET, Savona MR, Fesik SW..  (2019)  Discovery of Potent Myeloid Cell Leukemia-1 (Mcl-1) Inhibitors That Demonstrate in Vivo Activity in Mouse Xenograft Models of Human Cancer.,  62  (8): [PMID:30929420] [10.1021/acs.jmedchem.8b01991]

Source

Source(1):

• Scientific Literature