12-(2-Methylthiazol-4-yl)abieta-8,11,13-trien-18-amide

ID: ALA4461610

PubChem CID: 155528598

Max Phase: Preclinical

Molecular Formula: C24H32N2OS

Molecular Weight: 396.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(-c2cc3c(cc2C(C)C)CC[C@H]2[C@](C)(C(N)=O)CCC[C@]32C)cs1

Standard InChI:  InChI=1S/C24H32N2OS/c1-14(2)17-11-16-7-8-21-23(4,9-6-10-24(21,5)22(25)27)19(16)12-18(17)20-13-28-15(3)26-20/h11-14,21H,6-10H2,1-5H3,(H2,25,27)/t21-,23-,24-/m1/s1

Standard InChI Key:  HLWBFOYCMBYSPF-GMKZXUHWSA-N

Molfile:  

 
     RDKit          2D

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   31.9819   -7.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2680   -8.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2761   -6.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2761   -7.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9855   -6.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6950   -6.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6915   -7.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3977   -7.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1077   -7.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4046   -6.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1069   -6.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8185   -6.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8249   -5.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1138   -5.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4092   -5.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5391   -5.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2485   -5.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5440   -4.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6877   -5.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6835   -8.3948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.6875   -9.2197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1168   -4.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7802   -3.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5306   -3.0375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.7093   -3.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4539   -3.8148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2272   -2.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2639   -9.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  1  0
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  7 11  1  0
  8  9  1  0
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 11 12  2  0
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 13 14  2  0
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 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
  7 20  1  1
  8 21  1  6
  1 22  1  0
 15 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 23  1  0
 26 28  1  0
  1 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4461610

   ---

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: 396.60

Molecular Weight (Monoisotopic): 396.2235

AlogP: 5.74

#Rotatable Bonds: 3

Polar Surface Area: 55.98

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.54

CX LogP: 5.76

CX LogD: 5.76

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: 0.86

References

1. Ahonen TJ, Savinainen JR, Yli-Kauhaluoma J, Kalso E, Laitinen JT, Moreira VM..  (2018)  Discovery of 12-Thiazole Abietanes as Selective Inhibitors of the Human Metabolic Serine Hydrolase hABHD16A.,  9  (12): [PMID:30613338] [10.1021/acsmedchemlett.8b00442]

2. Hoover, Heather S; Blankman, Jacqueline L; Niessen, Sherry and Cravatt, Benjamin F.  2008-11-15  Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.  [PMID:18657971]

3. Ogasawara, Daisuke and 6 more authors.  2019-02-14  Discovery and Optimization of Selective and in Vivo Active Inhibitors of the Lysophosphatidylserine Lipase α/β-Hydrolase Domain-Containing 12 (ABHD12).  [PMID:30720278]

4. Arena, Chiara and 21 more authors.  2020-12-15  The endocannabinoid system dual-target ligand N-cycloheptyl-1,2-dihydro-5-bromo-1-(4-fluorobenzyl)-6-methyl-2-oxo-pyridine-3-carboxamide improves disease severity in a mouse model of multiple sclerosis.  [PMID:33002735]

Source

Source(1):

• Scientific Literature