Methyl 2-[((adamantan-1-yl)carbonyl)amino]-5-ethyl-4-methylthiophene-3-carboxylate

ID: ALA4476681

PubChem CID: 155538552

Max Phase: Preclinical

Molecular Formula: C20H27NO3S

Molecular Weight: 361.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1sc(NC(=O)C23CC4CC(CC(C4)C2)C3)c(C(=O)OC)c1C

Standard InChI:  InChI=1S/C20H27NO3S/c1-4-15-11(2)16(18(22)24-3)17(25-15)21-19(23)20-8-12-5-13(9-20)7-14(6-12)10-20/h12-14H,4-10H2,1-3H3,(H,21,23)

Standard InChI Key:  LMFJEFWVETVREV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    8.8010   -8.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1945   -9.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0100   -8.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4756   -9.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2485   -8.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7390   -9.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0474   -9.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5239  -10.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2316  -10.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7668  -10.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370  -10.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3583  -10.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6127   -9.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9456   -9.2326    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869   -9.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3200   -9.2986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8379  -11.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5046  -11.9117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584  -11.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0362   -9.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0449  -10.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9856  -12.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097   -9.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -8.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0553  -11.1557    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  1  0
 11 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476681

   ---

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: 361.51

Molecular Weight (Monoisotopic): 361.1712

AlogP: 4.56

#Rotatable Bonds: 4

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.58

CX Basic pKa: ┄

CX LogP: 6.02

CX LogD: 6.02

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: -1.09

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