N-Cyclopropylmethyl-7,8-dihydro-14beta-[3'-(methoxycarbonyl)propenamido]normorphinone

ID: ALA2179264

PubChem CID: 71455484

Max Phase: Preclinical

Molecular Formula: C25H28N2O6

Molecular Weight: 452.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)/C=C/C(=O)N[C@@]12CCC(=O)[C@@H]3Oc4c(O)ccc5c4[C@@]31CCN(CC1CC1)[C@@H]2C5

Standard InChI:  InChI=1S/C25H28N2O6/c1-32-20(31)7-6-19(30)26-25-9-8-17(29)23-24(25)10-11-27(13-14-2-3-14)18(25)12-15-4-5-16(28)22(33-23)21(15)24/h4-7,14,18,23,28H,2-3,8-13H2,1H3,(H,26,30)/b7-6+/t18-,23+,24+,25-/m1/s1

Standard InChI Key:  QZDANAWJLUZBMD-RDYFDFNXSA-N

Molfile:  

     RDKit          2D

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  7 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2179264

   methyl (E)-4-[[(4R,4aS,7aR,12bR)-3-(cyclopropylmethyl)-9-hydroxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]amino]-4-oxobut-2-enoate

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: 452.51

Molecular Weight (Monoisotopic): 452.1947

AlogP: 1.38

#Rotatable Bonds: 5

Polar Surface Area: 105.17

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.80

CX Basic pKa: 8.40

CX LogP: 1.78

CX LogD: 0.88

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.51

Np Likeness Score: 1.03

References

1. Moynihan HA, Derrick I, Broadbear JH, Greedy BM, Aceto MD, Harris LS, Purington LC, Thomas MP, Woods JH, Traynor JR, Husbands SM, Lewis JW..  (2012)  Fumaroylamino-4,5-epoxymorphinans and related opioids with irreversible μ opioid receptor antagonist effects.,  55  (22): [PMID:23043264] [10.1021/jm301096s]

Source

Source(1):

• Scientific Literature