(S)-2-amino-N-((R)-1-{[((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-ethyl)-3-(4-hydroxy-phenyl)-propionamide

ID: ALA235743

Cas Number: 66649-46-5

PubChem CID: 5490373

Max Phase: Preclinical

Molecular Formula: C23H29N5O5

Molecular Weight: 455.52

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(N)=O

Standard InChI:  InChI=1S/C23H29N5O5/c1-14(27-23(33)18(24)11-16-7-9-17(29)10-8-16)22(32)26-13-20(30)28-19(21(25)31)12-15-5-3-2-4-6-15/h2-10,14,18-19,29H,11-13,24H2,1H3,(H2,25,31)(H,26,32)(H,27,33)(H,28,30)/t14-,18+,19+/m1/s1

Standard InChI Key:  RJEUERNNQHNSKG-CCKFTAQKSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  1  0  0  0  0  0999 V2000
   -4.8333  -12.9458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1189  -12.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044  -12.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1189  -11.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044  -11.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903  -11.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763  -11.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9758  -10.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6953  -10.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064  -10.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619  -10.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044  -13.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899  -12.5333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754  -12.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610  -12.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754  -13.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465  -12.9458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610  -11.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680  -12.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824  -12.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824  -13.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969  -12.5333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114  -12.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0258  -12.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3114  -13.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0258  -14.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222  -15.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7359  -15.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4513  -15.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4487  -14.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7403  -12.9458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0258  -11.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7403  -13.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 17  1  0
  8  9  1  0
 15 18  2  0
  4  5  1  0
 17 19  1  0
  9 10  2  0
 19 20  1  0
 10  5  1  0
 20 21  2  0
  2  3  1  0
 20 22  1  0
  8 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  1  0
  3 12  2  0
 23 25  1  6
  1  2  1  0
 25 26  1  0
  3 13  1  0
 26 27  2  0
  6  7  1  0
 27 28  1  0
 13 14  1  0
 28 29  2  0
  2  4  1  1
 29 30  1  0
 30 33  2  0
 33 26  1  0
 14 15  1  0
 24 31  1  0
  7  8  2  0
 24 32  2  0
 14 16  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA235743

   Tyrosyl alanyl-glycyl-phenylalaninamide

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: 455.52

Molecular Weight (Monoisotopic): 455.2169

AlogP: -0.90

#Rotatable Bonds: 11

Polar Surface Area: 176.64

Molecular Species: NEUTRAL

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.50

CX Basic pKa: 7.73

CX LogP: -0.70

CX LogD: -1.06

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.26

Np Likeness Score: -0.15

References

1. Lee YS, Petrov R, Park CK, Ma SW, Davis P, Lai J, Porreca F, Vardanyan R, Hruby VJ..  (2007)  Development of novel enkephalin analogues that have enhanced opioid activities at both mu and delta opioid receptors.,  50  (22): [PMID:17927164] [10.1021/jm061465o]

2. Lee YS, Fernandes S, Kulkarani V, Mayorov A, Davis P, Ma SW, Brown K, Gillies RJ, Lai J, Porreca F, Hruby VJ..  (2010)  Design and synthesis of trivalent ligands targeting opioid, cholecystokinin, and melanocortin receptors for the treatment of pain.,  20  (14): [PMID:20547453] [10.1016/j.bmcl.2010.05.078]

3. Lee YS, Kulkarani V, Cowell SM, Ma SW, Davis P, Hanlon KE, Vanderah TW, Lai J, Porreca F, Vardanyan R, Hruby VJ..  (2011)  Development of potent μ and δ opioid agonists with high lipophilicity.,  54  (1): [PMID:21128594] [10.1021/jm100982d]

4. Wang Y, Zhao X, Gao X, Gan Y, Liu Y, Zhao X, Hu J, Ma X, Wu Y, Ma P, Liang X, Zhang X..  (2017)  Original endomorphin-1 analogues exhibit good analgesic effects with minimal implications for human sperm motility.,  27  (10): [PMID:28377055] [10.1016/j.bmcl.2017.03.067]

5. Dvorácskó S, Keresztes A, Mollica A, Stefanucci A, Macedonio G, Pieretti S, Zádor F, Walter FR, Deli MA, Kékesi G, Bánki L, Tuboly G, Horváth G, Tömböly C..  (2019)  Preparation of bivalent agonists for targeting the mu opioid and cannabinoid receptors.,  178  [PMID:31220675] [10.1016/j.ejmech.2019.05.037]

6. Mehr-Un-Nisa, Munawar MA, Rankin D, Hruby VJ, Porreca F, Lee YS..  (2021)  C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters.,  51  [PMID:34798381] [10.1016/j.bmc.2021.116509]

Source

Source(1):

• Scientific Literature