(S)-methyl 2-((4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydrothiazole-4-carboxamido)-3-(1H-imidazol-5-yl)propanoate

ID: ALA4207529

PubChem CID: 145975226

Max Phase: Preclinical

Molecular Formula: C18H20N4O4S

Molecular Weight: 388.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1N=C(c2ccccc2O)S[C@@H]1C

Standard InChI:  InChI=1S/C18H20N4O4S/c1-10-15(22-17(27-10)12-5-3-4-6-14(12)23)16(24)21-13(18(25)26-2)7-11-8-19-9-20-11/h3-6,8-10,13,15,23H,7H2,1-2H3,(H,19,20)(H,21,24)/t10-,13+,15-/m1/s1

Standard InChI Key:  WSMFZWOSGRIXPV-RIEGTJTDSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   20.3598  -21.6358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1811  -21.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4385  -20.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7725  -20.3723    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.1087  -20.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3346  -20.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1650  -19.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3847  -19.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7730  -20.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9496  -20.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7254  -21.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7719  -19.2573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2163  -20.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6599  -22.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3259  -23.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4728  -22.2143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9517  -22.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7646  -22.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2435  -23.4551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0987  -22.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6177  -23.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0966  -24.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8467  -25.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5068  -25.5437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1690  -25.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9181  -24.2871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0564  -23.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  5  6  1  0
  7 12  1  0
  3 13  1  6
  2 14  1  6
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 17 21  1  6
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4207529

   ---

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: 388.45

Molecular Weight (Monoisotopic): 388.1205

AlogP: 1.27

#Rotatable Bonds: 6

Polar Surface Area: 116.67

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.57

CX Basic pKa: 6.74

CX LogP: 1.60

CX LogD: 1.54

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: 0.15

References

1. Lin Z, Smith MD, Concepcion GP, Haygood MG, Olivera BM, Light A, Schmidt EW..  (2017)  Modulating the Serotonin Receptor Spectrum of Pulicatin Natural Products.,  80  (8): [PMID:28745513] [10.1021/acs.jnatprod.7b00317]

Source

Source(1):

• Scientific Literature