1N-[10,17-dihydroxy-4-methyl-(13R,14R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-yl]acetamide

ID: ALA3350139

PubChem CID: 118718764

Max Phase: Preclinical

Molecular Formula: C19H24N2O4

Molecular Weight: 344.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3C)[C@H]1O5

Standard InChI:  InChI=1S/C19H24N2O4/c1-10(22)20-12-5-6-19(24)14-9-11-3-4-13(23)16-15(11)18(19,17(12)25-16)7-8-21(14)2/h3-4,12,14,17,23-24H,5-9H2,1-2H3,(H,20,22)/t12-,14-,17+,18+,19-/m1/s1

Standard InChI Key:  WZKKHNQPRSDJFT-UPQOXJCWSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  1  0  0  0  0  0999 V2000
    0.2983   -2.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7112   -2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276   -2.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7112   -3.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974   -4.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2983   -1.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9405   -2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276   -1.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366   -0.4531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5313   -3.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147   -2.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5313   -2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9442   -4.3701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7491   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586   -4.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376   -1.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7663   -2.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328   -2.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1183   -1.5140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829   -3.6647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -2.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506   -4.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715   -5.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522   -4.4423    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  4  6  1  0
  7  2  1  0
  8  3  2  0
  9  8  1  0
 10 17  1  0
 11  4  1  0
  1 12  1  1
  2 13  1  0
 11 14  1  1
 15  5  2  0
 16 14  1  0
 17 12  1  0
 18  8  1  0
 19 11  1  0
  2 20  1  1
 21 16  2  0
 22 18  2  0
 23 15  1  0
 24 10  1  0
 25 16  1  0
  6  5  1  0
  7 10  1  1
 13 19  1  0
  9  7  1  0
 22 15  1  0
  4 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3350139

   ---

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: 344.41

Molecular Weight (Monoisotopic): 344.1736

AlogP: 0.68

#Rotatable Bonds: 1

Polar Surface Area: 82.03

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.14

CX Basic pKa: 8.95

CX LogP: -0.11

CX LogD: -1.42

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: 1.74

References

1. Portoghese PS, Larson DL, Sayre LM, Yim CB, Ronsisvalle G, Tam SW, Takemori AE..  (1986)  Opioid agonist and antagonist bivalent ligands. The relationship between spacer length and selectivity at multiple opioid receptors.,  29  (10): [PMID:3020244] [10.1021/jm00160a010]

Source

Source(1):

• Scientific Literature