(S)-N-((S)-1-amino-1-oxo-3-phenylpropan-2-yl)-2-((2S,5S,8S)-14-amino-2,8-dibenzyl-5-(hydroxymethyl)-4,7,10,13-tetraoxo-3,6,9,12-tetraazatetradecanamido)-5-(azetidine-1-carboximidamido)pentanamide

ID: ALA4285426

PubChem CID: 145993280

Max Phase: Preclinical

Molecular Formula: C43H57N11O8

Molecular Weight: 856.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CN)C(=O)N[C@@H](Cc1ccccc1)C(N)=O)N1CCC1

Standard InChI:  InChI=1S/C43H57N11O8/c44-25-36(56)48-26-37(57)49-33(23-29-14-6-2-7-15-29)40(60)53-35(27-55)42(62)52-34(24-30-16-8-3-9-17-30)41(61)50-31(18-10-19-47-43(46)54-20-11-21-54)39(59)51-32(38(45)58)22-28-12-4-1-5-13-28/h1-9,12-17,31-35,55H,10-11,18-27,44H2,(H2,45,58)(H2,46,47)(H,48,56)(H,49,57)(H,50,61)(H,51,59)(H,52,62)(H,53,60)/t31-,32-,33-,34-,35-/m0/s1

Standard InChI Key:  YGCUNPUGGWOAFR-ZZTWKDBPSA-N

Molfile:  

     RDKit          2D

 62 65  0  0  0  0  0  0  0  0999 V2000
   39.6349   -5.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3474   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0583   -3.5073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6324   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3474   -4.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9173   -3.9178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7734   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4884   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2034   -3.9178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4884   -2.6823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9185   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6335   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9185   -2.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6335   -2.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3484   -2.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0588   -2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0593   -1.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3434   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6318   -1.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6335   -4.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3485   -3.5073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0594   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7745   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0594   -4.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7745   -5.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4895   -3.9178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7745   -2.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.2045   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9196   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2045   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9196   -2.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6349   -2.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3495   -2.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3499   -1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6298   -1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9182   -1.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9196   -4.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6347   -3.5073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.3498   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0648   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3498   -4.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7757   -3.9178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.0648   -2.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4907   -3.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2058   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9208   -3.5073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.2058   -4.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4907   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2058   -2.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9193   -2.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6338   -2.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6343   -1.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9142   -1.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2026   -1.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6347   -5.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9198   -6.3943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9200   -7.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2050   -7.6340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6351   -7.6337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8462   -8.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6432   -8.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4306   -7.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  2  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  1
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 20  2  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  6
 24 25  1  0
 23 26  1  0
 23 27  2  0
 26 28  1  0
 28 29  1  0
 28 30  1  1
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
 29 37  2  0
 29 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  1  6
 40 42  1  0
 40 43  2  0
 42 44  1  0
 44 45  1  0
 45 46  1  0
 45 47  2  0
 44 48  1  1
 48 49  1  0
 49 50  2  0
 50 51  1  0
 51 52  2  0
 52 53  1  0
 53 54  2  0
 54 49  1  0
 41 55  1  0
 55  1  1  0
  1 56  1  0
 56 57  1  0
 57 58  2  0
 57 59  1  0
 59 60  1  0
 60 61  1  0
 61 62  1  0
 62 59  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4285426

   ---

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: 856.00

Molecular Weight (Monoisotopic): 855.4392

AlogP: -2.30

#Rotatable Bonds: 24

Polar Surface Area: 303.06

Molecular Species: BASE

HBA: 10

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.66

CX Basic pKa: 11.55

CX LogP: -3.02

CX LogD: -5.28

Aromatic Rings: 3

Heavy Atoms: 62

QED Weighted: 0.03

Np Likeness Score: -0.17

References

1. Alim K, Lefranc B, Sopkova-de Oliveira Santos J, Dubessy C, Picot M, Boutin JA, Vaudry H, Chartrel N, Vaudry D, Chuquet J, Leprince J..  (2018)  Design, Synthesis, Molecular Dynamics Simulation, and Functional Evaluation of a Novel Series of 26RFa Peptide Analogues Containing a Mono- or Polyalkyl Guanidino Arginine Derivative.,  61  (22): [PMID:30358997] [10.1021/acs.jmedchem.8b01332]

2. Georgsson, Jennie J and 15 more authors.  2014-07-24  GPR103 antagonists demonstrating anorexigenic activity in vivo: design and development of pyrrolo[2,3-c]pyridines that mimic the C-terminal Arg-Phe motif of QRFP26.  [PMID:24937104]

Source

Source(1):

• Scientific Literature