ID: ALA489057

Max Phase: Preclinical

Molecular Formula: C32H34N2O4

Molecular Weight: 510.63

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(C(=O)c1ccc2ccccc2c1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5

Standard InChI:  InChI=1S/C32H34N2O4/c1-33(30(36)23-9-8-20-4-2-3-5-21(20)16-23)24-12-13-32(37)26-17-22-10-11-25(35)28-27(22)31(32,29(24)38-28)14-15-34(26)18-19-6-7-19/h2-5,8-11,16,19,24,26,29,35,37H,6-7,12-15,17-18H2,1H3/t24-,26-,29+,31+,32-/m1/s1

Standard InChI Key:  LHRFRCCOWXEVBM-RQZMOBKGSA-N

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

Properties

Molecular Weight: 510.63

Molecular Weight (Monoisotopic): 510.2519

AlogP: 4.25

#Rotatable Bonds: 4

Polar Surface Area: 73.24

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.29

CX Basic pKa: 9.51

CX LogP: 3.58

CX LogD: 1.76

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.55

Np Likeness Score: 0.73

References

1. Kawai K, Hayakawa J, Miyamoto T, Imamura Y, Yamane S, Wakita H, Fujii H, Kawamura K, Matsuura H, Izumimoto N, Kobayashi R, Endo T, Nagase H..  (2008)  Design, synthesis, and structure-activity relationship of novel opioid kappa-agonists.,  16  (20): [PMID:18829333] [10.1016/j.bmc.2008.09.011]

2. Le Naour M, Lunzer MM, Powers MD, Portoghese PS..  (2012)  Opioid activity of spinally selective analogues of N-naphthoyl-β-naltrexamine in HEK-293 cells and mice.,  55  (2): [PMID:22136373] [10.1021/jm200902v]

Source

Source(1):

• Scientific Literature