17-Cyclopropylmethyl-3,14beta-dihydroxy-4,5alpha-epoxy-6beta-[(3'-methylformate-4'-pyridyl)carboxamido]morphinan

ID: ALA4584097

PubChem CID: 146408968

Max Phase: Preclinical

Molecular Formula: C28H31N3O6

Molecular Weight: 505.57

Molecule Type: Unknown

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  COC(=O)c1cnccc1C(=O)N[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5

Standard InChI:  InChI=1S/C28H31N3O6/c1-36-26(34)18-13-29-10-7-17(18)25(33)30-19-6-8-28(35)21-12-16-4-5-20(32)23-22(16)27(28,24(19)37-23)9-11-31(21)14-15-2-3-15/h4-5,7,10,13,15,19,21,24,32,35H,2-3,6,8-9,11-12,14H2,1H3,(H,30,33)/t19-,21-,24+,27+,28-/m1/s1

Standard InChI Key:  RXYSJDXUCZUPLZ-IBHWKQIPSA-N

Molfile:  

 
     RDKit          2D

 39 45  0  0  0  0  0  0  0  0999 V2000
    4.2498  -13.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580  -13.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4248  -13.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580  -14.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0248  -14.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8081  -14.9616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2997  -12.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0123  -13.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2247  -11.5242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4123  -12.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206  -13.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4747  -13.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4747  -14.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1956  -14.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8081  -12.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1874  -13.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8954  -13.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0622  -12.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749  -13.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4622  -10.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6247  -10.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749  -15.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6497  -15.3907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0122  -11.9659    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1936  -11.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1811  -10.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817  -15.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7067  -15.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1138  -15.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1245  -14.4906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6934  -16.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0998  -17.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9256  -17.3498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3433  -16.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9345  -15.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3483  -15.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1732  -15.2072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9371  -14.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5844  -15.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  2  0
  6  4  1  0
  7  2  1  0
  8  3  1  0
  9 15  1  0
 10  8  1  0
  1 11  1  1
 12  2  1  0
 13  4  1  0
 14  5  1  0
 15 11  1  0
 16  8  2  0
 17 13  1  0
  2 18  1  1
 19 16  1  0
 20 21  1  0
 21  9  1  0
 22 14  1  0
  4 23  1  1
  7 24  1  6
  6  5  1  0
  7  9  1  0
 17 12  1  0
  7 10  1  0
 19 14  2  0
 25 20  1  0
 26 25  1  0
 20 26  1  0
 13 27  1  1
 27 28  1  0
 28 29  1  0
 28 30  2  0
 29 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 29  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 37 39  1  0
M  END

Alternative Forms

  1. Parent:

    ALA4584097

    ---

Associated Targets(non-human)

Oprm1 Mu opioid receptor (1674 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprk1 Kappa opioid receptor (991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprd1 Delta opioid receptor (3127 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 505.57Molecular Weight (Monoisotopic): 505.2213AlogP: 1.94#Rotatable Bonds: 5
Polar Surface Area: 121.22Molecular Species: BASEHBA: 8HBD: 3
#RO5 Violations: 1HBA (Lipinski): 9HBD (Lipinski): 3#RO5 Violations (Lipinski): 1
CX Acidic pKa: 10.29CX Basic pKa: 9.51CX LogP: 1.15CX LogD: -0.67
Aromatic Rings: 2Heavy Atoms: 37QED Weighted: 0.53Np Likeness Score: 0.69

References

1. Zheng Y, Obeng S, Wang H, Jali AM, Peddibhotla B, Williams DA, Zou C, Stevens DL, Dewey WL, Akbarali HI, Selley DE, Zhang Y..  (2019)  Design, Synthesis, and Biological Evaluation of the Third Generation 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4'-pyridyl)carboxamido]morphinan (NAP) Derivatives as μ/κ Opioid Receptor Dual Selective Ligands.,  62  (2): [PMID:30608693] [10.1021/acs.jmedchem.8b01158]

Source