MePhe-Ala-Ala-Gly-Gly-MePhe-NH2

ID: ALA237413

PubChem CID: 23730841

Max Phase: Preclinical

Molecular Formula: C30H41N7O6

Molecular Weight: 595.70

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CN[C@@H](Cc1ccccc1)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)NCC(=O)NCC(=O)N(C)[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C30H41N7O6/c1-19(35-29(42)20(2)36-30(43)23(32-3)15-21-11-7-5-8-12-21)28(41)34-17-25(38)33-18-26(39)37(4)24(27(31)40)16-22-13-9-6-10-14-22/h5-14,19-20,23-24,32H,15-18H2,1-4H3,(H2,31,40)(H,33,38)(H,34,41)(H,35,42)(H,36,43)/t19-,20-,23-,24-/m0/s1

Standard InChI Key:  GDFUCYRWLGGIGG-TZYAJKAJSA-N

Molfile:  

     RDKit          2D

 43 44  0  0  1  0  0  0  0  0999 V2000
   14.2083  -10.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9228   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6373  -10.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3517   -9.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6373  -11.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4939   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0662  -10.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7807   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9228   -9.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2083   -8.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2111   -7.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4975   -7.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7820   -7.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7847   -8.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4989   -9.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0662  -11.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4952  -10.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7807   -9.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2096   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9241  -10.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2096   -9.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9241  -11.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6386   -9.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3530  -10.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0675   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7820  -10.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0675   -9.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4965   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2109  -10.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2109  -11.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9254   -9.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6399  -10.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9254   -9.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6399  -11.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3543   -9.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0688  -10.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0639  -11.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7775  -11.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4930  -11.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4903  -10.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7761   -9.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9254  -11.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3543  -11.5875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 20 22  2  0
  1  6  1  0
 20 23  1  0
 11 12  1  0
 23 24  1  0
  1  2  1  0
 24 25  1  0
 12 13  2  0
 25 26  1  0
  4  7  1  0
 25 27  2  0
 13 14  1  0
 26 28  1  0
  3  4  1  0
 28 29  1  0
 14 15  2  0
 29 30  2  0
 15 10  1  0
 29 31  1  0
  7  8  1  0
 31 32  1  0
  7 16  1  6
 31 33  1  0
 32 34  1  0
  8 17  1  0
 32 35  1  1
  2  9  1  1
 35 36  1  0
  8 18  2  0
 36 37  2  0
  3  5  2  0
 37 38  1  0
 17 19  1  0
 38 39  2  0
  9 10  1  0
 39 40  1  0
 19 20  1  0
 40 41  2  0
 41 36  1  0
  2  3  1  0
 34 42  2  0
 19 21  1  1
 34 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA237413

   Me-Phe-Ala-Ala-Gly-Gly-N(Me)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: 595.70

Molecular Weight (Monoisotopic): 595.3118

AlogP: -1.39

#Rotatable Bonds: 16

Polar Surface Area: 191.83

Molecular Species: NEUTRAL

HBA: 7

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.90

CX Basic pKa: 8.34

CX LogP: -1.24

CX LogD: -2.22

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.14

Np Likeness Score: -0.22

References

1. Hess S, Ovadia O, Shalev DE, Senderovich H, Qadri B, Yehezkel T, Salitra Y, Sheynis T, Jelinek R, Gilon C, Hoffman A..  (2007)  Effect of structural and conformation modifications, including backbone cyclization, of hydrophilic hexapeptides on their intestinal permeability and enzymatic stability.,  50  (24): [PMID:17983214] [10.1021/jm070836d]

Source

Source(1):

• Scientific Literature