(S)-2-(2-{2-[3-(2-Amino-ethyl)-1H-indol-5-yloxy]-acetylamino}-acetylamino)-3-(4-hydroxy-phenyl)-propionamide

ID: ALA159174

Cas Number: 133790-08-6

PubChem CID: 131670

Max Phase: Preclinical

Molecular Formula: C23H27N5O5

Molecular Weight: 453.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCc1c[nH]c2ccc(OCC(=O)NCC(=O)N[C@@H](Cc3ccc(O)cc3)C(N)=O)cc12

Standard InChI:  InChI=1S/C23H27N5O5/c24-8-7-15-11-26-19-6-5-17(10-18(15)19)33-13-22(31)27-12-21(30)28-20(23(25)32)9-14-1-3-16(29)4-2-14/h1-6,10-11,20,26,29H,7-9,12-13,24H2,(H2,25,32)(H,27,31)(H,28,30)/t20-/m0/s1

Standard InChI Key:  ZRVNSPYTGPNZTB-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  1  0  0  0  0  0999 V2000
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   10.0417  -11.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2667  -12.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0292  -12.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292  -10.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5667  -11.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -8.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042   -7.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000  -12.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -9.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -7.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9917  -10.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3000   -8.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -7.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -7.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7917  -11.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4792  -11.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  2  0
  3  1  1  0
  4  3  2  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  1  1  0
  9 19  1  0
 10 22  1  0
 11  2  1  0
 12 10  1  0
  6 13  1  6
 14  5  2  0
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 19 12  1  0
 20 25  1  0
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 22 21  1  0
 23 13  1  0
 24 30  2  0
 25 17  2  0
 26 23  1  0
 27 23  2  0
 28 33  1  0
 29 26  2  0
 30 27  1  0
 31 24  1  0
 32  4  1  0
 33 32  1  0
  2  4  1  0
 11 20  2  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA159174

   Serotonin-O-carboxymethyl-gly-tyr

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: 453.50

Molecular Weight (Monoisotopic): 453.2012

AlogP: 0.08

#Rotatable Bonds: 11

Polar Surface Area: 172.56

Molecular Species: BASE

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: 9.95

CX LogP: -1.02

CX LogD: -2.51

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.24

Np Likeness Score: -0.45

References

1. Perez M, Pauwels P, Palmier C, John GW, Valentin J, Halazy S.  (1995)  5-O-Carboxymethyl piperazide derivatives of serotonin: a new class of potent and selective 5-HT1D receptor agonists,  5  (7): [10.1016/0960-894X(95)00091-7]

Source

Source(1):

• Scientific Literature