((1S,2S,4R)-4-((R)-1-(4-methoxyphenyl)ethylamino)-2-(thiophen-3-yl)cyclohexyl)(4-(5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)methanone

ID: ALA1940366

PubChem CID: 57394808

Max Phase: Preclinical

Molecular Formula: C27H32F3N5O2S2

Molecular Weight: 579.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc([C@@H](C)N[C@@H]2CC[C@H](C(=O)N3CCN(c4nnc(C(F)(F)F)s4)CC3)[C@@H](c3ccsc3)C2)cc1

Standard InChI:  InChI=1S/C27H32F3N5O2S2/c1-17(18-3-6-21(37-2)7-4-18)31-20-5-8-22(23(15-20)19-9-14-38-16-19)24(36)34-10-12-35(13-11-34)26-33-32-25(39-26)27(28,29)30/h3-4,6-7,9,14,16-17,20,22-23,31H,5,8,10-13,15H2,1-2H3/t17-,20-,22+,23-/m1/s1

Standard InChI Key:  HOVSLXHXZHFJMS-ZZNFJVAJSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
    0.8708    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5829   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2949   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2949    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5829    0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0105    0.5604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7238    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395    0.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7214   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1531    0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8682    0.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8711    1.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1528    1.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406    1.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5862    1.7829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000    1.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824   -1.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9150   -2.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700   -3.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -3.1782    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498   -2.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570   -1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581   -0.6771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582   -1.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5616    0.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    0.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    0.1525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2742   -1.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    0.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894    1.3934    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5981    1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0165    0.8559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4662    0.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9291    2.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401    2.9906    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7491    2.4174    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458    3.0458    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  8 10  1  1
  3  4  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 18  2  0
  3 18  1  6
  9 11  2  0
  2 23  1  1
  4  5  1  0
 23 24  1  0
 11 12  1  0
 23 25  2  0
 24 26  1  0
  5  6  1  0
 12 13  2  0
 13 14  1  0
  5  7  1  1
 24 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 14 15  2  0
 28 31  1  0
 31 32  1  0
 15  9  1  0
  1  2  1  0
 13 16  1  0
  7  8  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 31  2  0
 16 17  1  0
 33 36  1  0
 18 19  1  0
 36 37  1  0
  1  6  1  0
 36 38  1  0
  8  9  1  0
 36 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1940366

   [(1S,2S,4R)-4-[[(1R)-1-(4-methoxyphenyl)ethyl]amino]-2-thiophen-3-ylcyclohexyl]-[4-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]piperazin-1-yl]methanone

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: 579.71

Molecular Weight (Monoisotopic): 579.1950

AlogP: 5.58

#Rotatable Bonds: 7

Polar Surface Area: 70.59

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.51

CX LogP: 5.11

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.39

Np Likeness Score: -1.48

References

1. Anthony Romero F, Hastings NB, Moningka R, Guo Z, Wang M, Di Salvo J, Lei Y, Trusca D, Deng Q, Tong V, Terebetski JL, Ball RG, Ujjainwalla F..  (2012)  The discovery of potent antagonists of NPBWR1 (GPR7).,  22  (2): [PMID:22197390] [10.1016/j.bmcl.2011.11.126]

Source

Source(1):

• Scientific Literature