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

ID: ALA4437695

PubChem CID: 155512643

Max Phase: Preclinical

Molecular Formula: C25H34INO2S

Molecular Weight: 412.62

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H34NO2S.HI/c1-16(2)18-12-17-8-9-22-24(3,10-7-11-25(22,4)23(27)28-6)20(17)13-19(18)21-14-29-15-26(21)5;/h12-16,22H,7-11H2,1-6H3;1H/q+1;/p-1/t22-,24-,25-;/m1./s1

Standard InChI Key:  ILKBFYFDPRRRAZ-NAQXRUJFSA-M

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   22.1343  -15.3120    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   22.2127  -19.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2169  -18.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5030  -18.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5111  -17.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5111  -17.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2205  -16.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9299  -17.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9265  -17.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6326  -18.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3427  -17.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6396  -16.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3419  -17.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0535  -16.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0598  -15.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3487  -15.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6442  -15.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7741  -15.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4835  -15.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7790  -14.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9226  -16.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9185  -18.6427    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.9225  -19.4676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3518  -14.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0152  -14.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7656  -13.2896    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.9442  -13.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6889  -14.0669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4989  -19.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9184  -20.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9067  -14.3165    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
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 24  1  0
  2 29  2  0
 23 30  1  0
 28 31  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: 412.62

Molecular Weight (Monoisotopic): 412.2305

AlogP: 5.55

#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: 3.09

CX LogD: 3.09

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: 1.61

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