(1S,3'R,6'R,7'S,8'E,14'R)-6-chloro-7',14'-dihydroxy-11'-methyl-12'-oxo-3,4-dihydro-2H-spiro[naphthalene-1,21'-[19]oxa[1,11]diazatetracyclo[13.7.2.0(3,6).0(18,23)]tetracosa [8,15,17,23]tetraene]-14'-carboxylic acid

ID: ALA4452403

PubChem CID: 155523253

Max Phase: Preclinical

Molecular Formula: C32H37ClN2O6

Molecular Weight: 581.11

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C/C=C/[C@H](O)[C@@H]2CC[C@H]2CN2C[C@@]3(CCCc4cc(Cl)ccc43)COc3ccc(cc32)[C@@](O)(C(=O)O)CC1=O

Standard InChI:  InChI=1S/C32H37ClN2O6/c1-34-13-3-5-27(36)24-9-6-21(24)17-35-18-31(12-2-4-20-14-23(33)8-10-25(20)31)19-41-28-11-7-22(15-26(28)35)32(40,30(38)39)16-29(34)37/h3,5,7-8,10-11,14-15,21,24,27,36,40H,2,4,6,9,12-13,16-19H2,1H3,(H,38,39)/b5-3+/t21-,24+,27-,31-,32+/m0/s1

Standard InChI Key:  VANZETYGPYBBAA-OPWIFKSFSA-N

Molfile:  

 
     RDKit          2D

 43 48  0  0  0  0  0  0  0  0999 V2000
    5.0660  -10.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730   -9.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921   -9.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3765  -11.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1712  -11.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444   -8.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7745   -9.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7716   -8.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0563   -7.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0581   -9.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3401   -9.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6287   -9.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291  -10.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471  -10.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5256   -8.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276   -8.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9028  -10.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8497  -10.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5378  -11.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2794  -10.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3286  -10.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6398   -9.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0662   -9.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0538   -7.0539    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1149   -8.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5611   -7.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3631   -7.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8808   -8.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7375   -8.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7425   -8.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2997   -9.2611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3067   -9.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8639  -10.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7564  -10.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2750  -10.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0710  -10.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6892  -11.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8499   -8.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8960   -9.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1417   -8.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5857   -6.7425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9709   -7.1417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3208   -9.3459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  3 17  1  0
  4  5  1  0
  5 18  1  0
  6 11  2  0
 10  7  2  0
  7  8  1  0
  8  9  2  0
  9  6  1  0
 10 11  1  0
  1 10  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14  1  1  0
  3 15  1  0
 15 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
 21 23  1  0
  9 24  1  0
 23 25  1  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 23 34  1  0
 23 35  1  1
 35 36  1  0
 35 37  2  0
 31 38  1  0
 16 39  1  0
 26 40  1  0
 39 40  1  0
 27 41  1  1
 26 42  1  1
 16 43  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4452403

   ---

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: 581.11

Molecular Weight (Monoisotopic): 580.2340

AlogP: 3.89

#Rotatable Bonds: 1

Polar Surface Area: 110.54

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.43

CX Basic pKa: 4.74

CX LogP: 2.60

CX LogD: 0.58

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.44

Np Likeness Score: 0.65

References

1. Rescourio G, Gonzalez AZ, Jabri S, Belmontes B, Moody G, Whittington D, Huang X, Caenepeel S, Cardozo M, Cheng AC, Chow D, Dou H, Jones A, Kelly RC, Li Y, Lizarzaburu M, Lo MC, Mallari R, Meleza C, Rew Y, Simonovich S, Sun D, Turcotte S, Yan X, Wong SG, Yanez E, Zancanella M, Houze J, Medina JC, Hughes PE, Brown SP..  (2019)  Discovery and in Vivo Evaluation of Macrocyclic Mcl-1 Inhibitors Featuring an α-Hydroxy Phenylacetic Acid Pharmacophore or Bioisostere.,  62  (22): [PMID:31736296] [10.1021/acs.jmedchem.9b01310]

Source

Source(1):

• Scientific Literature