(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)-6-(3-isobutylguanidino)hexanamide

ID: ALA4288785

PubChem CID: 145990522

Max Phase: Preclinical

Molecular Formula: C45H63N11O8

Molecular Weight: 886.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CNC(=N)NCCCC[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

Standard InChI:  InChI=1S/C45H63N11O8/c1-29(2)26-51-45(48)49-21-13-12-20-33(41(61)54-34(40(47)60)22-30-14-6-3-7-15-30)53-43(63)36(24-32-18-10-5-11-19-32)55-44(64)37(28-57)56-42(62)35(23-31-16-8-4-9-17-31)52-39(59)27-50-38(58)25-46/h3-11,14-19,29,33-37,57H,12-13,20-28,46H2,1-2H3,(H2,47,60)(H,50,58)(H,52,59)(H,53,63)(H,54,61)(H,55,64)(H,56,62)(H3,48,49,51)/t33-,34-,35-,36-,37-/m0/s1

Standard InChI Key:  UKFYGZNEYFRKRR-LTLCPEALSA-N

Molfile:  

     RDKit          2D

 64 66  0  0  0  0  0  0  0  0999 V2000
   40.0636  -25.1557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3373  -25.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6351  -25.1140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3132  -26.3718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0634  -24.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7778  -23.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7776  -23.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4921  -22.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4877  -21.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2022  -21.4418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7733  -21.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4877  -22.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0587  -21.8543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9167  -21.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6311  -21.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3456  -21.8543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6311  -20.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0601  -21.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7745  -21.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0601  -20.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7745  -20.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4889  -20.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2029  -20.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2034  -19.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4838  -18.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7728  -19.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7745  -22.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4890  -21.4418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2035  -21.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9179  -21.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2035  -22.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9179  -23.0918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6325  -21.8543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9179  -20.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3470  -21.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0614  -21.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3470  -20.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0614  -20.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7761  -20.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4901  -20.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4906  -19.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7711  -18.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0600  -19.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0614  -22.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.7759  -21.4418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4904  -21.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2048  -21.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9193  -21.8543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2048  -20.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6338  -21.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3482  -21.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0627  -21.4418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.3482  -22.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6338  -20.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3482  -20.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0612  -20.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7752  -20.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7757  -19.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0561  -18.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3451  -19.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0154  -26.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7416  -26.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4437  -26.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7656  -25.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  5  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9 10  1  0
  9 11  1  0
  9 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  1
 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
 19 27  2  0
 19 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  6
 31 32  1  0
 30 33  1  0
 30 34  2  0
 33 35  1  0
 35 36  1  0
 35 37  1  1
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  2  0
 43 38  1  0
 36 44  2  0
 36 45  1  0
 45 46  1  0
 46 47  1  0
 46  8  1  6
 47 48  1  0
 47 49  2  0
 48 50  1  0
 50 51  1  0
 51 52  1  0
 51 53  2  0
 50 54  1  1
 54 55  1  0
 55 56  2  0
 56 57  1  0
 57 58  2  0
 58 59  1  0
 59 60  2  0
 60 55  1  0
  4 61  1  0
 61 62  1  0
 62 63  1  0
 62 64  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4288785

   ---

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: 886.07

Molecular Weight (Monoisotopic): 885.4861

AlogP: -1.37

#Rotatable Bonds: 27

Polar Surface Area: 311.85

Molecular Species: BASE

HBA: 10

HBD: 12

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 14

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.45

CX Basic pKa: 11.70

CX LogP: -1.39

CX LogD: -3.75

Aromatic Rings: 3

Heavy Atoms: 64

QED Weighted: 0.02

Np Likeness Score: -0.03

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