1N-[10-hydroxy-4-methyl-14-oxo-(13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-17-yl]-4-(4-nitrophenyl)-(Z)-2-butenamide

ID: ALA607068

PubChem CID: 46878245

Max Phase: Preclinical

Molecular Formula: C26H25N3O6

Molecular Weight: 475.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(NC(=O)/C=C/c2ccc([N+](=O)[O-])cc2)[C@H]1C5

Standard InChI:  InChI=1S/C26H25N3O6/c1-28-13-12-25-22-16-5-8-18(30)23(22)35-24(25)19(31)10-11-26(25,20(28)14-16)27-21(32)9-4-15-2-6-17(7-3-15)29(33)34/h2-9,20,24,30H,10-14H2,1H3,(H,27,32)/b9-4+/t20-,24+,25+,26-/m1/s1

Standard InChI Key:  PMHKQZZWOMGKBX-IAYRCESESA-N

Molfile:  

     RDKit          2D

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M  CHG  2   8   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA607068

   (E)-N-[(4R,4aS,7aR,12bR)-9-hydroxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-3-(4-nitrophenyl)prop-2-enamide

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: 475.50

Molecular Weight (Monoisotopic): 475.1743

AlogP: 2.49

#Rotatable Bonds: 4

Polar Surface Area: 122.01

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.79

CX Basic pKa: 7.73

CX LogP: 2.90

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.40

Np Likeness Score: 0.72

References

1. Sebastian A, Bidlack JM, Jiang Q, Deecher D, Teitler M, Glick SD, Archer S..  (1993)  14 beta-[(p-nitrocinnamoyl)amino]morphinones, 14 beta-[(p-nitrocinnamoyl)amino]-7,8-dihydromorphinones, and their codeinone analogues: synthesis and receptor activity.,  36  (21): [PMID:7693944] [10.1021/jm00073a015]

2. Nieland NP, Moynihan HA, Carrington S, Broadbear J, Woods JH, Traynor JR, Husbands SM, Lewis JW..  (2006)  Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effect of substitution in the aromatic ring of cinnamoylaminomorphinones and codeinones.,  49  (17): [PMID:16913723] [10.1021/jm0604777]

Source

Source(1):

• Scientific Literature