4,5alpha-Epoxy-3,6beta, 14-trihydroxy-6alpha-(2-carboxyallyl)-17-methylmorphinnan gama-lactone

ID: ALA2310924

PubChem CID: 71717287

Max Phase: Preclinical

Molecular Formula: C21H23NO5

Molecular Weight: 369.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC2(CCC3(O)[C@H]4Cc5ccc(O)c6c5[C@@]3(CCN4C)C2O6)OC1=O

Standard InChI:  InChI=1S/C21H23NO5/c1-11-10-19(27-17(11)24)5-6-21(25)14-9-12-3-4-13(23)16-15(12)20(21,18(19)26-16)7-8-22(14)2/h3-4,14,18,23,25H,1,5-10H2,2H3/t14-,18?,19?,20+,21?/m1/s1

Standard InChI Key:  MVSABGMEQVNJCP-FWXNZYCQSA-N

Molfile:  

     RDKit          2D

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   -4.1029   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1029   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3884   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3884   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740   -0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595   -0.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595   -1.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2450   -0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305   -0.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305   -1.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2450   -2.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8489   -2.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740    0.4715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564   -1.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1369   -1.1060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2756   -2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494   -2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -1.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5890   -1.3360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0344   -3.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    0.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583    1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3884   -4.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401    0.1464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  7  1  0
  1  6  2  0
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  7  8  1  0
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  9 11  1  0
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 11 12  1  0
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  5 15  1  0
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  8 16  1  0
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 10 18  1  1
 18 17  1  0
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 13 20  1  0
 20 21  1  0
 21 22  1  0
 19 22  1  0
 22 23  2  0
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  9 25  1  0
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  4 27  1  0
  8 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2310924

   (4R,12bS)-4a,9-dihydroxy-3-methyl-3'-methylidenespiro[2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,5'-oxolane]-2'-one

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: 369.42

Molecular Weight (Monoisotopic): 369.1576

AlogP: 1.42

#Rotatable Bonds: ┄

Polar Surface Area: 79.23

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.12

CX Basic pKa: 8.83

CX LogP: 1.48

CX LogD: 0.28

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: 2.13

References

1. Koolpe GA, Nelson WL, Gioannini TL, Angel L, Simon EJ..  (1984)  Diastereomeric 6-desoxy-6-spiro-alpha-methylene-gamma-butyrolactone derivatives of naltrexone and oxymorphone. Selective irreversible inhibition of naltrexone binding in an opioid receptor preparation by a conformationally restricted michael acceptor ligand.,  27  (12): [PMID:6209395] [10.1021/jm00378a032]

2. Koolpe GA, Nelson WL, Gioannini TL, Angel L, Simon EJ..  (1984)  Diastereomeric 6-desoxy-6-spiro-alpha-methylene-gamma-butyrolactone derivatives of naltrexone and oxymorphone. Selective irreversible inhibition of naltrexone binding in an opioid receptor preparation by a conformationally restricted michael acceptor ligand.,  27  (12): [PMID:6209395] [10.1021/jm00378a032]

3. Koolpe GA, Nelson WL, Gioannini TL, Angel L, Appelmans N, Simon EJ..  (1985)  Opioid agonists and antagonists. 6-Desoxy-6-substituted lactone, epoxide, and glycidate ester derivatives of naltrexone and oxymorphone.,  28  (7): [PMID:2409280] [10.1021/jm00145a018]

4. Koolpe GA, Nelson WL, Gioannini TL, Angel L, Appelmans N, Simon EJ..  (1985)  Opioid agonists and antagonists. 6-Desoxy-6-substituted lactone, epoxide, and glycidate ester derivatives of naltrexone and oxymorphone.,  28  (7): [PMID:2409280] [10.1021/jm00145a018]

Source

Source(1):

• Scientific Literature