(S)-N-((S)-1-((S)-1-((S)-1-amino-1-oxo-3-phenylpropan-2-ylamino)-5-guanidino-1-oxopentan-2-ylamino)-4-methyl-1-oxopentan-2-yl)pyrrolidine-2-carboxamide

ID: ALA2181306

PubChem CID: 71455644

Max Phase: Preclinical

Molecular Formula: C26H42N8O4

Molecular Weight: 530.67

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@@H]1CCCN1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C26H42N8O4/c1-16(2)14-21(34-23(36)18-10-6-12-30-18)25(38)32-19(11-7-13-31-26(28)29)24(37)33-20(22(27)35)15-17-8-4-3-5-9-17/h3-5,8-9,16,18-21,30H,6-7,10-15H2,1-2H3,(H2,27,35)(H,32,38)(H,33,37)(H,34,36)(H4,28,29,31)/t18-,19-,20-,21-/m0/s1

Standard InChI Key:  AWVQBUHYVKKMTF-TUFLPTIASA-N

Molfile:  

     RDKit          2D

 38 39  0  0  0  0  0  0  0  0999 V2000
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    6.2567  -16.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3693  -14.7184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7742  -15.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5338  -16.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910  -16.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8637  -17.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5970  -15.4536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0182  -14.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2458  -15.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406  -14.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6171  -14.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0425  -13.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414  -12.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8690  -13.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5395  -15.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9360  -16.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5148  -16.9643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7626  -16.2724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2659  -14.0515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0884  -14.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1126  -12.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4895  -14.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3160  -14.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7171  -15.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3402  -13.3744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7615  -12.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891  -13.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5880  -12.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3646  -11.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3903  -10.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7858  -11.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6095  -11.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0370  -10.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6374   -9.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8141   -9.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0134  -11.9764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  8  1  0
 11 20  1  0
 23 27  1  0
 30 38  1  0
  1  2  1  0
  2  4  1  6
  4  3  2  0
  2  5  1  0
  6  7  1  0
  7  5  1  0
  6  1  1  0
  8  9  1  0
  9 11  1  0
 11 10  2  0
  9 12  1  1
 12 13  1  0
 13 14  1  0
 13 15  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 20 21  1  0
 21 23  1  0
 23 22  2  0
 21 24  1  6
 24 25  1  0
 25 26  1  0
 26 16  1  0
 27 28  1  0
 28 30  1  0
 30 29  2  0
 28 31  1  1
 31 33  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2181306

   H-Pro-Leu-Arg-Phe-NH2

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 530.67

Molecular Weight (Monoisotopic): 530.3329

AlogP: -0.77

#Rotatable Bonds: 15

Polar Surface Area: 204.32

Molecular Species: BASE

HBA: 6

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.05

CX Basic pKa: 11.69

CX LogP: -0.92

CX LogD: -5.00

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.08

Np Likeness Score: 0.07

References

1. Nichols R, Bass C, Demers L, Larsen B, Li E, Blewett N, Converso-Baran K, Russell MW, Westfall MV..  (2012)  Structure-activity studies of RFamide-related peptide-1 identify a functional receptor antagonist and novel cardiac myocyte signaling pathway involved in contractile performance.,  55  (17): [PMID:22909119] [10.1021/jm300760m]

Source

Source(1):

• Scientific Literature