Methyl 2-[((adamantan-1-yl)carbonyl)amino]-5-phenylthiophene-3-carboxylate

ID: ALA4557732

PubChem CID: 155554628

Max Phase: Preclinical

Molecular Formula: C23H25NO3S

Molecular Weight: 395.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(-c2ccccc2)sc1NC(=O)C12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C23H25NO3S/c1-27-21(25)18-10-19(17-5-3-2-4-6-17)28-20(18)24-22(26)23-11-14-7-15(12-23)9-16(8-14)13-23/h2-6,10,14-16H,7-9,11-13H2,1H3,(H,24,26)

Standard InChI Key:  HXLZHXBLBJSXOH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   34.5054   -2.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8989   -2.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7143   -2.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1800   -2.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9529   -2.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4433   -2.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7518   -3.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2282   -3.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9360   -3.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4712   -3.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2414   -4.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0627   -4.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3171   -3.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6500   -2.7611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.9912   -3.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0244   -2.8272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5423   -4.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2090   -5.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3628   -4.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7406   -3.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7493   -4.0494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6899   -6.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2141   -2.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0478   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2715   -1.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6631   -2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8362   -3.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6123   -3.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 11  2  0
 13 16  1  0
 12 17  1  0
 17 18  1  0
 17 19  2  0
 16 20  1  0
 20 21  2  0
 20  6  1  0
 18 22  1  0
 15 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557732

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 395.52

Molecular Weight (Monoisotopic): 395.1555

AlogP: 5.36

#Rotatable Bonds: 4

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.50

CX Basic pKa: ┄

CX LogP: 6.06

CX LogD: 6.06

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -0.94

References

1. Mugnaini C, Rabbito A, Brizzi A, Palombi N, Petrosino S, Verde R, Di Marzo V, Ligresti A, Corelli F..  (2019)  Synthesis of novel 2-(1-adamantanylcarboxamido)thiophene derivatives. Selective cannabinoid type 2 (CB2) receptor agonists as potential agents for the treatment of skin inflammatory disease.,  161  [PMID:30359820] [10.1016/j.ejmech.2018.09.070]

Source

Source(1):

• Scientific Literature