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

ID: ALA4216860

PubChem CID: 145972374

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-DGFSRKRXSA-N

Molfile:  

     RDKit          2D

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   20.4753  -14.6484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2966  -14.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5541  -13.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8880  -13.3849    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.2243  -13.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4502  -13.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2805  -12.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5003  -12.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8886  -13.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0651  -13.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8410  -14.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8875  -12.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3319  -13.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7755  -15.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4415  -16.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5884  -15.2269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0673  -15.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8802  -15.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3591  -16.4677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2142  -15.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7332  -16.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2121  -17.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9623  -18.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6224  -18.5563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2846  -18.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0337  -17.2997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1720  -16.3841    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  1
 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:

   

   ALA4216860

   ---

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