US9340517, 478

ID: ALA3986831

PubChem CID: 127054280

Max Phase: Preclinical

Molecular Formula: C31H40Cl2N4O4

Molecular Weight: 603.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](CN1CC[C@H](CNC(=O)c2ccc(Cl)c(Cl)c2)N[C@H](CCN2CCC(C(=O)O)CC2)C1=O)c1ccccc1

Standard InChI:  InChI=1S/C31H40Cl2N4O4/c1-2-21(22-6-4-3-5-7-22)20-37-17-12-25(19-34-29(38)24-8-9-26(32)27(33)18-24)35-28(30(37)39)13-16-36-14-10-23(11-15-36)31(40)41/h3-9,18,21,23,25,28,35H,2,10-17,19-20H2,1H3,(H,34,38)(H,40,41)/t21-,25-,28-/m1/s1

Standard InChI Key:  LBTPHRXHXMLVPM-LFGPKHSOSA-N

Molfile:  

     RDKit          2D

 41 44  0  0  1  0  0  0  0  0999 V2000
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    3.7225    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703    0.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510   -0.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852   -0.3846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    1.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245    2.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    3.5008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702    4.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    4.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444    5.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4139    6.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1852    8.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7870    8.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041   10.0737    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6175    7.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4990    8.3831    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8462    6.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -0.3847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048   -2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9016   -3.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5555   -4.3709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0513   -4.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7022   -5.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8572   -7.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614   -6.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7106   -5.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5056   -8.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8282   -9.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7021   -8.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -2.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342    0.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6545    1.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1169    0.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5590   -0.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5388   -1.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0764   -1.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 13  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  1
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 25  1  0
 28 31  1  0
 31 32  2  0
 31 33  1  0
 22 34  1  0
 34  5  1  0
 34 35  2  0
  3 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986831

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 603.59

Molecular Weight (Monoisotopic): 602.2427

AlogP: 4.66

#Rotatable Bonds: 11

Polar Surface Area: 101.98

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.71

CX Basic pKa: 9.20

CX LogP: 1.40

CX LogD: 1.41

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.35

Np Likeness Score: -0.63

References

1.  (2016)  Methods of modulating the activity of the MC5 receptor and treatment of conditions related to this receptor, 

Source

Source(1):

• BindingDB Database