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

ID: ALA2181307

PubChem CID: 71453914

Max Phase: Preclinical

Molecular Formula: C21H35N7O3

Molecular Weight: 433.56

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H35N7O3/c1-13(2)11-15(22)19(30)27-16(9-6-10-26-21(24)25)20(31)28-17(18(23)29)12-14-7-4-3-5-8-14/h3-5,7-8,13,15-17H,6,9-12,22H2,1-2H3,(H2,23,29)(H,27,30)(H,28,31)(H4,24,25,26)/t15-,16-,17-/m0/s1

Standard InChI Key:  ZVGJPQMEEYQNAU-ULQDDVLXSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   19.8252  -19.8025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2487  -19.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4751  -19.8315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0716  -19.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8493  -18.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2729  -17.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8735  -16.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0999  -17.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7710  -19.8898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1700  -20.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7464  -21.3148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9970  -20.6219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4993  -18.4023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3222  -18.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3464  -16.9879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7499  -17.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7216  -19.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5487  -19.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9480  -19.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5728  -17.7240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9964  -17.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2228  -17.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8234  -17.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5970  -16.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6227  -14.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0206  -15.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8448  -15.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2704  -14.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8726  -14.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0487  -14.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2470  -16.3239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4 13  1  0
 16 20  1  0
 23 31  1  0
  1  2  1  0
  2  4  1  0
  4  3  2  0
  2  5  1  1
  5  6  1  0
  6  7  1  0
  6  8  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 13 14  1  0
 14 16  1  0
 16 15  2  0
 14 17  1  6
 17 18  1  0
 18 19  1  0
 19  9  1  0
 20 21  1  0
 21 23  1  0
 23 22  2  0
 21 24  1  1
 24 26  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2181307

   H-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: 433.56

Molecular Weight (Monoisotopic): 433.2801

AlogP: -0.68

#Rotatable Bonds: 13

Polar Surface Area: 189.21

Molecular Species: BASE

HBA: 5

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.40

CX Basic pKa: 11.81

CX LogP: -0.78

CX LogD: -3.65

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.12

Np Likeness Score: 0.20

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