1N-[4-cyclopropylmethyl-10-hydroxy-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: ALA611136

PubChem CID: 11849365

Max Phase: Preclinical

Molecular Formula: C29H29N3O6

Molecular Weight: 515.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)N[C@@]12CCC(=O)[C@@H]3Oc4c(O)ccc5c4[C@@]31CCN(CC1CC1)[C@@H]2C5

Standard InChI:  InChI=1S/C29H29N3O6/c33-21-9-6-19-15-23-29(30-24(35)10-5-17-3-7-20(8-4-17)32(36)37)12-11-22(34)27-28(29,25(19)26(21)38-27)13-14-31(23)16-18-1-2-18/h3-10,18,23,27,33H,1-2,11-16H2,(H,30,35)/b10-5+/t23-,27+,28+,29-/m1/s1

Standard InChI Key:  USUATCCCIDHRPH-DNIKMYEQSA-N

Molfile:  

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M  CHG  2  36   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA611136

   (E)-N-[(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]-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: 515.57

Molecular Weight (Monoisotopic): 515.2056

AlogP: 3.27

#Rotatable Bonds: 6

Polar Surface Area: 122.01

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.80

CX Basic pKa: 8.40

CX LogP: 3.51

CX LogD: 2.62

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.34

Np Likeness Score: 0.50

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