3-Ethyl-4-[18-(methoxycarbonyl)abieta-8,11,13-trien-12-yl]-2-methylthiazol-3-ium iodide

ID: ALA4526442

PubChem CID: 155544066

Max Phase: Preclinical

Molecular Formula: C27H38INO2S

Molecular Weight: 440.67

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[n+]1c(-c2cc3c(cc2C(C)C)CC[C@H]2[C@](C)(C(=O)OC)CCC[C@]32C)csc1C.[I-]

Standard InChI:  InChI=1S/C27H38NO2S.HI/c1-8-28-18(4)31-16-23(28)21-15-22-19(14-20(21)17(2)3)10-11-24-26(22,5)12-9-13-27(24,6)25(29)30-7;/h14-17,24H,8-13H2,1-7H3;1H/q+1;/p-1/t24-,26-,27-;/m1./s1

Standard InChI Key:  DWSUSTSPXPUZHN-PWZZUJFHSA-M

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   13.9418  -15.1882    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   14.0491  -19.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0532  -18.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3393  -18.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3475  -17.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3475  -18.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0569  -16.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7663  -17.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7628  -18.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4690  -18.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1790  -18.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.1782  -17.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8898  -16.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8962  -16.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.7590  -16.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7548  -18.8697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7588  -19.6946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1882  -14.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8516  -14.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6020  -13.5124    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7806  -13.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5253  -14.2898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2986  -12.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3352  -19.6874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7547  -20.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7430  -14.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1336  -13.9903    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
 27 29  1  0
  2 30  2  0
 23 31  1  0
 28 32  1  0
 32 33  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: 440.67

Molecular Weight (Monoisotopic): 440.2618

AlogP: 6.34

#Rotatable Bonds: 4

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: 2.57

CX LogD: 2.57

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: 1.32

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