(S)-2-amino-N1-((S)-1-((S)-2-((S)-1-((S)-1-((S)-1-amino-1-oxo-3-phenylpropan-2-ylamino)-5-guanidino-1-oxopentan-2-ylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)pyrrolidin-1-yl)-4-methyl-1-oxopentan-2-yl)succinamide

ID: ALA2181304

PubChem CID: 71452084

Max Phase: Preclinical

Molecular Formula: C36H59N11O7

Molecular Weight: 757.94

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(N)=O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C36H59N11O7/c1-20(2)16-26(45-34(53)28-13-9-15-47(28)35(54)27(17-21(3)4)46-31(50)23(37)19-29(38)48)33(52)43-24(12-8-14-42-36(40)41)32(51)44-25(30(39)49)18-22-10-6-5-7-11-22/h5-7,10-11,20-21,23-28H,8-9,12-19,37H2,1-4H3,(H2,38,48)(H2,39,49)(H,43,52)(H,44,51)(H,45,53)(H,46,50)(H4,40,41,42)/t23-,24-,25-,26-,27-,28-/m0/s1

Standard InChI Key:  HXUIOTWFFCZTGT-QUQVWLGBSA-N

Molfile:  

     RDKit          2D

 54 55  0  0  0  0  0  0  0  0999 V2000
    5.2265  -25.6395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0591  -25.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0338  -24.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4607  -24.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4789  -26.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837  -27.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5105  -27.7529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2647  -27.0545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2797  -24.8838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6813  -24.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9019  -23.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5003  -24.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2545  -23.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6495  -22.7287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2227  -22.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4685  -22.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8909  -24.7833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7160  -24.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8281  -23.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2312  -24.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9919  -25.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6509  -25.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3207  -26.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0546  -24.0487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4781  -23.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7046  -24.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3011  -23.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0787  -22.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5022  -21.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1029  -21.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3293  -21.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0004  -24.1360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3993  -24.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9758  -25.5610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2264  -24.8681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7287  -22.6486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5517  -22.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5758  -21.2342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9793  -21.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9510  -23.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7780  -23.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1775  -24.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8023  -21.9703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2258  -21.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4522  -21.9993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0529  -21.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8264  -20.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8520  -19.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2499  -19.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0743  -19.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4999  -19.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1020  -18.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2782  -18.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4764  -20.5702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
 12 17  1  0
 20 24  1  0
 27 36  1  0
 39 43  1  0
 46 54  1  0
  1  2  1  0
  2  4  1  0
  4  3  2  0
  2  5  1  6
  5  6  1  0
  6  7  2  0
  6  8  1  0
  9 10  1  0
 10 12  1  0
 12 11  2  0
 10 13  1  1
 13 14  1  0
 14 15  1  0
 14 16  1  0
 17 18  1  0
 18 20  1  6
 20 19  2  0
 18 21  1  0
 22 23  1  0
 23 21  1  0
 22 17  1  0
 24 25  1  0
 25 27  1  0
 27 26  2  0
 25 28  1  1
 28 29  1  0
 29 30  1  0
 29 31  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 36 37  1  0
 37 39  1  0
 39 38  2  0
 37 40  1  6
 40 41  1  0
 41 42  1  0
 42 32  1  0
 43 44  1  0
 44 46  1  0
 46 45  2  0
 44 47  1  1
 47 49  1  0
 48 49  2  0
 49 50  1  0
 50 51  2  0
 51 52  1  0
 52 53  2  0
 53 48  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2181304

   H-Asn-Leu-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: 757.94

Molecular Weight (Monoisotopic): 757.4599

AlogP: -1.80

#Rotatable Bonds: 22

Polar Surface Area: 310.81

Molecular Species: BASE

HBA: 9

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 14

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.83

CX Basic pKa: 11.58

CX LogP: -2.50

CX LogD: -4.56

Aromatic Rings: 1

Heavy Atoms: 54

QED Weighted: 0.04

Np Likeness Score: -0.04

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