ID: ALA514774

Max Phase: Preclinical

Molecular Formula: C29H33NO4

Molecular Weight: 459.59

Molecule Type: Small molecule

Representations

Synonyms (1): 14-O-Phenylpropylnaltrexone
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C1CC[C@@]2(OCCCc3ccccc3)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5

Standard InChI:  InChI=1S/C29H33NO4/c31-22-11-10-21-17-24-29(33-16-4-7-19-5-2-1-3-6-19)13-12-23(32)27-28(29,25(21)26(22)34-27)14-15-30(24)18-20-8-9-20/h1-3,5-6,10-11,20,24,27,31H,4,7-9,12-18H2/t24-,27+,28+,29-/m1/s1

Standard InChI Key:  KOXWKZKLXNZQAO-ZLPBPMGLSA-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: 459.59

Molecular Weight (Monoisotopic): 459.2410

AlogP: 4.18

#Rotatable Bonds: 7

Polar Surface Area: 59.00

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.12

CX Basic pKa: 8.98

CX LogP: 4.45

CX LogD: 3.13

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.63

Np Likeness Score: 1.18

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. Moynihan H, Jales AR, Greedy BM, Rennison D, Broadbear JH, Purington L, Traynor JR, Woods JH, Lewis JW, Husbands SM..  (2009)  14 beta-O-cinnamoylnaltrexone and related dihydrocodeinones are mu opioid receptor partial agonists with predominant antagonist activity.,  52  (6): [PMID:19253983] [10.1021/jm8012272]

3. Spetea M, Windisch P, Guo Y, Bileviciute-Ljungar I, Schütz J, Asim MF, Berzetei-Gurske IP, Riba P, Kiraly K, Fürst S, Al-Khrasani M, Schmidhammer H..  (2011)  Synthesis and pharmacological activities of 6-glycine substituted 14-phenylpropoxymorphinans, a novel class of opioids with high opioid receptor affinities and antinociceptive potencies.,  54  (4): [PMID:21235243] [10.1021/jm101211p]

Source

Source(1):

• Scientific Literature