8alpha-H-2beta-Ethyl-2alpha-methoxymethyl-salvinorin ether

ID: ALA3622710

PubChem CID: 122191989

Max Phase: Preclinical

Molecular Formula: C25H34O7

Molecular Weight: 446.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@]1(COC)C[C@@H](C(=O)OC)[C@]2(C)CC[C@@H]3C(=O)O[C@H](c4ccoc4)C[C@]3(C)[C@H]2C1=O

Standard InChI:  InChI=1S/C25H34O7/c1-6-25(14-29-4)11-17(21(27)30-5)23(2)9-7-16-22(28)32-18(15-8-10-31-13-15)12-24(16,3)19(23)20(25)26/h8,10,13,16-19H,6-7,9,11-12,14H2,1-5H3/t16-,17+,18+,19+,23+,24+,25-/m1/s1

Standard InChI Key:  PSXFNRVJRFXGLI-RXSHMUQTSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.4277    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    2.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    2.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7457    4.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9502    5.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721    6.7481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721    6.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232    5.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389   -3.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8426   -4.5544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1807   -4.3938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1361    1.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907    0.0732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3694    1.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0581    2.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8473   -5.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278   -2.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4036    1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6067   -0.5164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835   -0.5051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7058   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385    3.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7357   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 13 15  1  1
 20 21  1  0
 20 22  2  0
  3 20  1  6
  4 23  2  0
 11 24  2  0
  1 25  1  0
 25 26  1  0
 21 27  1  0
  6 28  1  6
  9 29  1  6
 10 30  1  6
  5 31  1  1
  1 32  1  1
 26 33  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3622710

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 446.54

Molecular Weight (Monoisotopic): 446.2305

AlogP: 4.11

#Rotatable Bonds: 5

Polar Surface Area: 92.04

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.63

Np Likeness Score: 2.13

References

1. Lee DY, Deng G, Ma Z, Xu W, Yang L, Liu J, Dai R, Liu-Chen LY..  (2015)  Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists.,  25  (20): [PMID:26330078] [10.1016/j.bmcl.2015.06.092]

Source

Source(1):

• Scientific Literature