(S)-3-hydroxypropyl 6-chloro-4-(1-cyclopropylethyl)-3-oxo-3,4-dihydropyrazin-2-yl(2,6-dichloro-4-(difluoromethoxy)phenyl)carbamate

ID: ALA4087161

PubChem CID: 137643390

Max Phase: Preclinical

Molecular Formula: C20H20Cl3F2N3O5

Molecular Weight: 526.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](C1CC1)n1cc(Cl)nc(N(C(=O)OCCCO)c2c(Cl)cc(OC(F)F)cc2Cl)c1=O

Standard InChI:  InChI=1S/C20H20Cl3F2N3O5/c1-10(11-3-4-11)27-9-15(23)26-17(18(27)30)28(20(31)32-6-2-5-29)16-13(21)7-12(8-14(16)22)33-19(24)25/h7-11,19,29H,2-6H2,1H3/t10-/m0/s1

Standard InChI Key:  SKAYQQFMGIMCKB-JTQLQIEISA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    2.9459  -15.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459  -16.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6579  -16.8669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699  -16.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699  -15.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6579  -15.2169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6579  -14.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3724  -13.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9434  -13.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958  -13.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7833  -13.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320  -16.8722    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0838  -16.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0856  -15.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0826  -17.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3665  -18.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3650  -18.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794  -19.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969  -18.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7948  -18.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6532  -17.6923    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5085  -17.6927    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0793  -20.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3648  -20.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6503  -20.1703    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647  -21.4080    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989  -16.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5127  -16.8742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001  -15.6356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2278  -16.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9418  -16.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6569  -16.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3707  -16.8783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
 10  8  1  0
 11 10  1  0
  8 11  1  0
  2 12  1  0
  4 13  1  0
  5 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 16 21  1  0
 20 22  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 13 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087161

   ---

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: 526.75

Molecular Weight (Monoisotopic): 525.0437

AlogP: 5.43

#Rotatable Bonds: 9

Polar Surface Area: 93.89

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.70

CX LogD: 4.70

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: -0.75

References

1. Hartz RA, Vrudhula VM, Ahuja VT, Grace JE, Lodge NJ, Bronson JJ, Macor JE..  (2017)  Synthesis and evaluation of prodrugs of corticotropin-releasing factor-1 (CRF1) receptor antagonist BMS-665053 leading to improved oral bioavailability.,  27  (6): [PMID:28223020] [10.1016/j.bmcl.2017.02.015]

Source

Source(1):

• Scientific Literature