17-(cyclopropylmethyl)-6beta-(benzyloxy)-4,5alpha-epoxy-3,14-dihydroxymorphinan

ID: ALA2112732

PubChem CID: 71456227

Max Phase: Preclinical

Molecular Formula: C27H31NO4

Molecular Weight: 433.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc2c3c1OC1[C@H](OCc4ccccc4)CCC4(O)C(C2)N(CC2CC2)CCC314

Standard InChI:  InChI=1S/C27H31NO4/c29-20-9-8-19-14-22-27(30)11-10-21(31-16-18-4-2-1-3-5-18)25-26(27,23(19)24(20)32-25)12-13-28(22)15-17-6-7-17/h1-5,8-9,17,21-22,25,29-30H,6-7,10-16H2/t21-,22?,25?,26?,27?/m1/s1

Standard InChI Key:  LLYKFTJDMLXUDK-XVMPFKDUSA-N

Molfile:  

     RDKit          2D

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   10.6207   -2.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7923   -6.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9958   -4.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2248   -6.1331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7955   -4.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0026   -5.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3651   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1705   -4.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7966   -5.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3834   -5.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2112732

   (7R)-3-(cyclopropylmethyl)-7-phenylmethoxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol

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: 433.55

Molecular Weight (Monoisotopic): 433.2253

AlogP: 3.54

#Rotatable Bonds: 5

Polar Surface Area: 62.16

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.30

CX Basic pKa: 9.47

CX LogP: 3.21

CX LogD: 1.42

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.76

Np Likeness Score: 1.35

References

1. Nelson TD, Davis RD, Nelson WL..  (1994)  Synthesis and opioid receptor affinity of a series of aralkyl ethers of 6 alpha- and 6 beta-naltrexol.,  37  (25): [PMID:7996538] [10.1021/jm00051a003]

2. Davis RD, Nelson WL..  (1995)  Isothiocyanate-substituted benzyl ether opioid receptor ligands derived from 6 beta-naltrexol.,  38  (3): [PMID:7853350] [10.1021/jm00003a020]

Source

Source(1):

• Scientific Literature