CH3(Ph)CH(CO)His-Trp-Ala-Val-DAla-His-DPro(psi)Phe-NH2 (S)

ID: ALA2111953

PubChem CID: 10260590

Max Phase: Preclinical

Molecular Formula: C57H72N14O8

Molecular Weight: 1081.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)[C@H](C)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H](C)c1ccccc1)C(=O)N[C@H](C)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N1CCC[C@@H]1CN[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C57H72N14O8/c1-33(2)49(56(78)66-35(4)52(74)69-48(26-41-29-60-32-64-41)57(79)71-22-14-19-42(71)30-62-45(50(58)72)23-37-15-8-6-9-16-37)70-53(75)36(5)65-54(76)46(24-39-27-61-44-21-13-12-20-43(39)44)68-55(77)47(25-40-28-59-31-63-40)67-51(73)34(3)38-17-10-7-11-18-38/h6-13,15-18,20-21,27-29,31-36,42,45-49,61-62H,14,19,22-26,30H2,1-5H3,(H2,58,72)(H,59,63)(H,60,64)(H,65,76)(H,66,78)(H,67,73)(H,68,77)(H,69,74)(H,70,75)/t34-,35+,36-,42+,45-,46-,47-,48-,49-/m0/s1

Standard InChI Key:  MENDYSYDOLPPDA-JITBRIPHSA-N

Molfile:  

     RDKit          2D

 79 85  0  0  1  0  0  0  0  0999 V2000
   14.0320   -2.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2923   -2.6459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4281   -2.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0953   -2.6310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6327   -2.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3532   -3.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6089   -2.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5121   -2.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -2.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2375   -2.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6992   -2.6310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8449   -2.6459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738   -4.8755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -2.6310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7444   -3.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9047   -2.6459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526   -4.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2810   -2.6459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9365   -3.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2040   -0.5252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3401   -4.7467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5756   -5.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9365   -3.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6963   -2.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3532   -3.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0667   -4.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4774   -0.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675   -0.1041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0766   -5.1728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9350   -2.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5537   -2.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797    0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8644   -5.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0125   -2.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4205   -2.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337   -5.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3683   -2.2743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9414   -2.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8496   -4.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6945   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0370   -1.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4281   -1.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6327   -1.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6187   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252   -1.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5071   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2425   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6251   -2.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6963   -1.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0125   -3.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4205   -3.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6030   -2.2793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7444   -3.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6531   -2.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7260   -3.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0495   -1.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9117   -5.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9414   -1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -2.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9350   -1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5537   -1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -3.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6327   -3.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4579   -4.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0309   -4.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7260   -4.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4395   -3.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0158   -6.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7739   -6.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6327   -4.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -4.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1530   -3.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4395   -5.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1530   -4.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4205   -5.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 17  1  0
  4 25  1  0
 16  5  1  6
  6 13  1  0
  7  1  1  0
  8  5  1  0
  9 15  1  0
 10 19  1  0
 11 12  1  0
  7 12  1  6
 20 13  1  1
 14 18  1  0
 21 15  1  6
 16  3  1  0
 17 34  1  0
 18  4  2  0
 19 33  1  0
 20  9  1  0
 21 10  1  0
 22 43  1  0
 23 42  1  0
 24  4  1  0
 21 25  1  0
 26 37  1  0
  7 27  1  0
 28 27  1  0
 29 30  1  0
 20 30  1  0
 31 29  1  0
 32 28  1  0
 33  8  1  0
 34 11  1  0
 35 31  2  0
 36 32  2  0
 37 40  1  6
 38  6  1  0
 39 24  2  0
 40 51  1  0
 41  2  1  0
 42 28  2  0
 43 29  2  0
 44  1  2  0
 45  3  2  0
 46  6  2  0
 47  8  2  0
 48 10  2  0
 49  9  2  0
 50 11  2  0
 41 51  1  6
 52 26  2  0
 37 53  1  0
 38 54  1  0
 55 26  1  0
 16 56  1  0
 57  2  1  0
 58 53  1  0
 59 57  1  0
 60 24  1  0
 41 61  1  0
 38 62  1  6
 33 63  1  1
 34 64  1  6
 65 39  1  0
 66 54  2  0
 67 54  1  0
 68 56  1  0
 69 56  1  0
 70 58  2  0
 71 58  1  0
 72 60  2  0
 73 72  1  0
 74 67  2  0
 75 66  1  0
 76 71  2  0
 77 70  1  0
 78 76  1  0
 79 74  1  0
 61 59  1  0
 23 36  1  0
 77 78  2  0
 14 39  1  0
 73 65  2  0
 22 35  1  0
 79 75  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2111953

   (2S)-N-[(2R)-1-[[(2S)-1-[(2R)-2-[[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]methyl]pyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]-2-[[(2S)-2-[[(2S)-2-[[(2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-2-phenylpropanoyl]amino]propano

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: 1081.29

Molecular Weight (Monoisotopic): 1080.5658

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Leban JJ, Landavazo A, McDermed JD, Diliberto EJ, Jansen M, Stockstill B, Kull FC..  (1994)  Potent gastrin-releasing peptide (GRP) antagonists derived from GRP (19-27) with a C-terminal DPro psi [CH2NH]Phe-NH2 and N-terminal aromatic residues.,  37  (4): [PMID:8120863] [10.1021/jm00030a002]

Source

Source(1):

• Scientific Literature