(S)-2-((S)-3-((S)-5-guanidino-2-palmitamidopentanamido)-3-(naphthalen-1-yl)propanamido)-3-phenylpropanoic acid

ID: ALA4286093

PubChem CID: 145993093

Max Phase: Preclinical

Molecular Formula: C44H64N6O5

Molecular Weight: 757.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(=O)N[C@@H](Cc1ccccc1)C(=O)O)c1cccc2ccccc12

Standard InChI:  InChI=1S/C44H64N6O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-29-40(51)48-37(28-21-30-47-44(45)46)42(53)50-38(36-27-20-25-34-24-18-19-26-35(34)36)32-41(52)49-39(43(54)55)31-33-22-15-14-16-23-33/h14-16,18-20,22-27,37-39H,2-13,17,21,28-32H2,1H3,(H,48,51)(H,49,52)(H,50,53)(H,54,55)(H4,45,46,47)/t37-,38-,39-/m0/s1

Standard InChI Key:  KOEOPUGYYQQUHH-IGMOWHQGSA-N

Molfile:  

     RDKit          2D

 55 57  0  0  0  0  0  0  0  0999 V2000
   19.9028  -10.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1975  -10.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4867  -10.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4811   -9.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7724   -9.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7668   -8.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0581   -7.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0525   -7.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3417   -6.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3361   -5.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6274   -5.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6218   -4.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9131   -4.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9075   -3.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1967   -3.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1932   -2.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8972   -9.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6136  -10.7565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4917  -12.9982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0571  -13.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8542  -12.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2392  -13.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4421  -14.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3924  -15.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0073  -15.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1858  -15.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7510  -15.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1360  -16.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9539  -16.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8008  -14.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5140  -11.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4772  -10.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1705  -10.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1400   -9.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8333   -9.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5552   -9.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5837  -10.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3056  -10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3361  -11.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6428  -11.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9209  -11.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8924  -10.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7554  -10.3827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7989   -7.9191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8141   -7.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1096   -6.6756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5317   -6.7031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3333  -10.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0226  -11.6028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0378  -10.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3464   -9.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0661   -9.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0813   -8.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0918  -12.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2747  -12.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  1 17  2  0
  1 18  1  0
 22 30  1  0
 19 20  1  0
 20 22  1  0
 22 21  2  0
 20 23  1  1
 23 25  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 32 31  1  6
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 33 42  2  0
 37 42  1  0
 32 33  1  0
 32 43  1  0
 50 43  1  0
 44 45  1  0
 45 46  1  0
 45 47  2  0
 18 48  1  0
 48 50  1  0
 50 49  2  0
 48 51  1  1
 51 52  1  0
 52 53  1  0
 53 44  1  0
 31 54  1  0
 54 55  2  0
 54 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4286093

   ---

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: 757.03

Molecular Weight (Monoisotopic): 756.4938

AlogP: 7.43

#Rotatable Bonds: 28

Polar Surface Area: 186.50

Molecular Species: ZWITTERION

HBA: 5

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 3.83

CX Basic pKa: 11.92

CX LogP: 6.19

CX LogD: 6.19

Aromatic Rings: 3

Heavy Atoms: 55

QED Weighted: 0.02

Np Likeness Score: -0.05

References

1. Naik H, Gauthier T, Singh S, Jois S..  (2018)  Design of novel lipidated peptidomimetic conjugates for targeting EGFR heterodimerization in HER2 + cancer.,  28  (22): [PMID:30314880] [10.1016/j.bmcl.2018.10.005]

Source

Source(1):

• Scientific Literature