(5-(Phenyl(pyridine-2-yl)methyl)thiophene-2-carbonyl)-L-arginine

ID: ALA4559463

PubChem CID: 155557799

Max Phase: Preclinical

Molecular Formula: C23H25N5O3S

Molecular Weight: 451.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)c1ccc(C(c2ccccc2)c2ccccn2)s1)C(=O)O

Standard InChI:  InChI=1S/C23H25N5O3S/c24-23(25)27-14-6-10-17(22(30)31)28-21(29)19-12-11-18(32-19)20(15-7-2-1-3-8-15)16-9-4-5-13-26-16/h1-5,7-9,11-13,17,20H,6,10,14H2,(H,28,29)(H,30,31)(H4,24,25,27)/t17-,20?/m0/s1

Standard InChI Key:  JMCWYUHSKMIRKD-DIMJTDRSSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   30.4136  -23.9974    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.1587  -23.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0539  -22.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2404  -22.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8530  -23.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8827  -24.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9024  -24.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5871  -23.6092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3111  -24.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0156  -23.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3308  -24.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6264  -25.2586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0548  -25.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9959  -22.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7003  -22.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6807  -21.4964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3850  -21.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3655  -20.2423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1092  -21.4624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0277  -23.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6138  -22.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0340  -21.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6248  -21.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7990  -21.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3839  -21.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7954  -22.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6083  -24.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7813  -24.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3662  -24.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7733  -25.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6041  -25.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0196  -24.8227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 11 13  2  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  5 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 20 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559463

   ---

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: 451.55

Molecular Weight (Monoisotopic): 451.1678

AlogP: 2.77

#Rotatable Bonds: 10

Polar Surface Area: 141.19

Molecular Species: ZWITTERION

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.28

CX Basic pKa: 11.98

CX LogP: 1.01

CX LogD: 1.01

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.18

Np Likeness Score: -0.60

References

1. Rowley JA, Reid RC, Poon EKY, Wu KC, Lim J, Lohman RJ, Hamidon JK, Yau MK, Halili MA, Durek T, Iyer A, Fairlie DP..  (2020)  Potent Thiophene Antagonists of Human Complement C3a Receptor with Anti-Inflammatory Activity.,  63  (2): [PMID:31910011] [10.1021/acs.jmedchem.9b00927]

Source

Source(1):

• Scientific Literature