1N-[10-hydroxy-4-methyl-14-oxo-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-17-yl]-2-sulfanylacetamide

ID: ALA606710

PubChem CID: 20833183

Max Phase: Preclinical

Molecular Formula: C19H22N2O4S

Molecular Weight: 374.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(NC(=O)CS)[C@H]1C5

Standard InChI:  InChI=1S/C19H22N2O4S/c1-21-7-6-18-15-10-2-3-11(22)16(15)25-17(18)12(23)4-5-19(18,13(21)8-10)20-14(24)9-26/h2-3,13,17,22,26H,4-9H2,1H3,(H,20,24)/t13-,17+,18+,19-/m1/s1

Standard InChI Key:  IFWCCHXFUMLVAF-WEZQJLTASA-N

Molfile:  

     RDKit          2D

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    2.9464   -2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089   -2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089   -3.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -3.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1840   -3.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -4.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464   -4.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714   -2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0589   -3.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715   -4.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2965   -4.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920   -4.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464   -1.5470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9506   -3.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -1.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609   -1.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -2.2614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1840   -5.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0590   -5.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1839   -2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5964   -1.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5964   -2.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214   -1.5470    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2146   -5.3682    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -1.3954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  1  0
 10  6  1  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  2  0
  5  4  1  0
  5 14  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 10 15  1  0
  2 16  1  0
  6 17  1  1
 16 18  1  0
 18 17  1  0
 16 19  1  0
  1 20  1  1
  9 21  2  0
 13 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 10 27  1  1
  2 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA606710

   N-[(4R,4As,7aR,12bR)-9-hydroxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-2-sulfanylacetamide

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: 374.46

Molecular Weight (Monoisotopic): 374.1300

AlogP: 0.80

#Rotatable Bonds: 2

Polar Surface Area: 78.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.28

CX Basic pKa: 7.45

CX LogP: 0.70

CX LogD: 0.49

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: 1.28

References

1. Archer S, Seyed-Mozaffari A, Jiang Q, Bidlack JM..  (1994)  14 alpha,14' beta-[Dithiobis[(2-oxo-2,1-ethanediyl)imino]]bis (7,8-dihydromorphinone) and 14 alpha,14' beta-[dithiobis[(2-oxo-2,1- ethanediyl)imino]]bis[7,8-dihydro-N-(cyclopropylmethyl)normorphinone]: chemistry and opioid binding properties.,  37  (11): [PMID:7515442] [10.1021/jm00037a008]

Source

Source(1):

• Scientific Literature