4-[18-(Methoxycarbonyl)abieta-8,11,13-trien-12-yl]-2,3-dimethylthiazol-3-ium iodide

ID: ALA4519648

PubChem CID: 155541769

Max Phase: Preclinical

Molecular Formula: C26H36INO2S

Molecular Weight: 426.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]1(C)CCC[C@]2(C)c3cc(-c4csc(C)[n+]4C)c(C(C)C)cc3CC[C@@H]12.[I-]

Standard InChI:  InChI=1S/C26H36NO2S.HI/c1-16(2)19-13-18-9-10-23-25(4,11-8-12-26(23,5)24(28)29-7)21(18)14-20(19)22-15-30-17(3)27(22)6;/h13-16,23H,8-12H2,1-7H3;1H/q+1;/p-1/t23-,25-,26-;/m1./s1

Standard InChI Key:  UGRQLVBFZDKBDF-HPMHZXFDSA-M

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.3373  -15.1263    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.6844  -19.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885  -18.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746  -18.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4016  -17.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981  -17.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1043  -18.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5251  -16.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5315  -15.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3943  -16.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902  -18.6592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3942  -19.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8235  -14.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4869  -14.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2373  -13.3020    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159  -13.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1606  -14.0793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9339  -12.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9705  -19.4769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3900  -20.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3783  -14.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  3  4  1  1
  5  6  1  0
  5  7  1  0
  6  3  1  0
  3  9  1  0
  8  7  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
  8 21  1  1
  9 22  1  6
  2 23  1  0
 16 24  1  0
 24 25  2  0
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 26 27  1  0
 27 28  2  0
 28 24  1  0
 27 29  1  0
  2 30  2  0
 23 31  1  0
 28 32  1  0
M  CHG  2   1  -1  28   1
M  END

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: 426.65

Molecular Weight (Monoisotopic): 426.2461

AlogP: 5.85

#Rotatable Bonds: 3

Polar Surface Area: 30.18

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: 2.21

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: 1.43

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