ID: ALA326684

Max Phase: Preclinical

Molecular Formula: C19H23NO4

Molecular Weight: 329.40

Molecule Type: Small molecule

Representations

Canonical SMILES:  CO[C@@]12CCC(=O)[C@]3(C)Oc4c(O)ccc5c4[C@@]31CCN(C)[C@@H]2C5

Standard InChI:  InChI=1S/C19H23NO4/c1-17-14(22)6-7-19(23-3)13-10-11-4-5-12(21)16(24-17)15(11)18(17,19)8-9-20(13)2/h4-5,13,21H,6-10H2,1-3H3/t13-,17+,18+,19-/m1/s1

Standard InChI Key:  DENICFHULARDRG-WEZQJLTASA-N

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

Properties

Molecular Weight: 329.40

Molecular Weight (Monoisotopic): 329.1627

AlogP: 1.79

#Rotatable Bonds: 1

Polar Surface Area: 59.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.06

CX Basic pKa: 8.37

CX LogP: 1.83

CX LogD: 0.94

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: 2.07

References

1. Greiner E, Spetea M, Krassnig R, Schüllner F, Aceto M, Harris LS, Traynor JR, Woods JH, Coop A, Schmidhammer H..  (2003)  Synthesis and biological evaluation of 14-alkoxymorphinans. 18. N-substituted 14-phenylpropyloxymorphinan-6-ones with unanticipated agonist properties: extending the scope of common structure-activity relationships.,  46  (9): [PMID:12699394] [10.1021/jm021118o]

2. Spetea M, Schüllner F, Moisa RC, Berzetei-Gurske IP, Schraml B, Dörfler C, Aceto MD, Harris LS, Coop A, Schmidhammer H..  (2004)  Synthesis and biological evaluation of 14-alkoxymorphinans. 21. Novel 4-alkoxy and 14-phenylpropoxy derivatives of the mu opioid receptor antagonist cyprodime.,  47  (12): [PMID:15163203] [10.1021/jm031126k]

3. Lattanzi R, Spetea M, Schüllner F, Rief SB, Krassnig R, Negri L, Schmidhammer H..  (2005)  Synthesis and biological evaluation of 14-alkoxymorphinans. 22.(1) Influence of the 14-alkoxy group and the substitution in position 5 in 14-alkoxymorphinan-6-ones on in vitro and in vivo activities.,  48  (9): [PMID:15857143] [10.1021/jm040894o]

4. Turnaturi R, Aricò G, Ronsisvalle G, Parenti C, Pasquinucci L..  (2016)  Multitarget opioid ligands in pain relief: New players in an old game.,  108  [PMID:26656913] [10.1016/j.ejmech.2015.11.028]

5. Dumitrascuta M, Ben Haddou T, Guerrieri E, Noha SM, Schläfer L, Schmidhammer H, Spetea M..  (2017)  Synthesis, Pharmacology, and Molecular Docking Studies on 6-Desoxo-N-methylmorphinans as Potent μ-Opioid Receptor Agonists.,  60  (22): [PMID:29053268] [10.1021/acs.jmedchem.7b01363]

Source

Source(1):

• Scientific Literature