2-Amino-N-[6-(3-tert-butyl-4-hydroxy-benzyl)-2,5,8-trioxo-1,4,7triaza-cyclotridec-9-yl]-3-phenyl-propionamide

ID: ALA2371264

PubChem CID: 10864575

Max Phase: Preclinical

Molecular Formula: C30H41N5O5

Molecular Weight: 551.69

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(C[C@@H]2NC(=O)[C@@H](NC(=O)[C@@H](N)Cc3ccccc3)CCCCNC(=O)CNC2=O)ccc1O

Standard InChI:  InChI=1S/C30H41N5O5/c1-30(2,3)21-15-20(12-13-25(21)36)17-24-28(39)33-18-26(37)32-14-8-7-11-23(29(40)35-24)34-27(38)22(31)16-19-9-5-4-6-10-19/h4-6,9-10,12-13,15,22-24,36H,7-8,11,14,16-18,31H2,1-3H3,(H,32,37)(H,33,39)(H,34,38)(H,35,40)/t22-,23-,24-/m0/s1

Standard InChI Key:  WQCVKFYFRFRIGI-HJOGWXRNSA-N

Molfile:  

     RDKit          2D

 40 42  0  0  0  0  0  0  0  0999 V2000
    6.3165   -1.8325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5594   -2.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8422   -2.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144   -2.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -1.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2499   -3.0554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2899   -2.4458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5660   -1.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0431   -2.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9354   -4.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8690   -2.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1134   -2.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2715   -5.1246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8338   -0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7623   -1.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4074   -1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0703   -1.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6843   -3.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2149   -0.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3508   -1.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2848   -3.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935   -3.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5721   -5.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2825   -0.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7992   -1.7393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4712   -0.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -2.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6375   -0.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4563   -5.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7306   -1.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4961   -2.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6608   -2.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8723   -3.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -1.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -3.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6759   -4.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1052   -4.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0233   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6328   -1.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0427   -1.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  7  1  0
  5  1  1  0
  6  3  1  0
  9  7  1  6
  8 15  2  0
  9  2  1  0
 10 21  1  0
 11  4  1  0
 12  8  1  0
 13 10  1  0
 14 24  2  0
 15 19  1  0
  5 16  1  1
 17  2  2  0
 18  4  2  0
 19 16  1  0
 20  3  2  0
 21  6  1  0
 11 22  1  6
 23 10  2  0
 24 26  1  0
 25 11  1  0
 26 19  2  0
 27 22  1  0
 28 14  1  0
 29 36  1  0
 30 12  1  0
 31 12  1  0
 32 12  1  0
 33  9  1  0
 34 27  2  0
 35 27  1  0
 36 37  1  0
 37 33  1  0
 38 35  2  0
 39 34  1  0
 40 38  1  0
 14  8  1  0
 13 29  1  0
 40 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2371264

   H-Phe-Lys(1)-Tyr(3-tBu)-Gly-(1)

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: 551.69

Molecular Weight (Monoisotopic): 551.3108

AlogP: 1.19

#Rotatable Bonds: 6

Polar Surface Area: 162.65

Molecular Species: NEUTRAL

HBA: 6

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.08

CX Basic pKa: 7.71

CX LogP: 1.71

CX LogD: 1.23

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.32

Np Likeness Score: 0.64

References

1. Haramura M, Okamachi A, Tsuzuki K, Yogo K, Ikuta M, Kozono T, Takanashi H, Murayama E..  (2002)  Design and synthesis of motilin antagonists derived from the [1-4] fragment of porcine motilin.,  45  (3): [PMID:11806718] [10.1021/jm010332u]

Source

Source(1):

• Scientific Literature