2-(3-Ethyl-8-methoxy-5-oxy-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-methoxy-acrylic acid methyl ester

ID: ALA56717

Chembl Id: CHEMBL56717

PubChem CID: 11058760

Max Phase: Preclinical

Molecular Formula: C23H30N2O5

Molecular Weight: 414.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H]1C[N+]2([O-])CCc3c([nH]c4cccc(OC)c34)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

Standard InChI:  InChI=1S/C23H30N2O5/c1-5-14-12-25(27)10-9-15-21-18(7-6-8-20(21)29-3)24-22(15)19(25)11-16(14)17(13-28-2)23(26)30-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19+,25?/m1/s1

Standard InChI Key:  KXNRITUKNSFMGJ-CUKABGIGSA-N

Alternative Forms

1. Parent:

   

   ALA56717

   methyl (E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-5-oxido-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-5-ium-2-yl]-3-methoxyprop-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: 414.50

Molecular Weight (Monoisotopic): 414.2155

AlogP: 3.84

#Rotatable Bonds: 5

Polar Surface Area: 83.61

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.23

CX LogP: 2.18

CX LogD: 2.18

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: 1.89

References

1. Takayama H, Ishikawa H, Kurihara M, Kitajima M, Aimi N, Ponglux D, Koyama F, Matsumoto K, Moriyama T, Yamamoto LT, Watanabe K, Murayama T, Horie S..  (2002)  Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.,  45  (9): [PMID:11960505] [10.1021/jm010576e]

2. Chakraborty S, Uprety R, Slocum ST, Irie T, Le Rouzic V, Li X, Wilson LL, Scouller B, Alder AF, Kruegel AC, Ansonoff M, Varadi A, Eans SO, Hunkele A, Allaoa A, Kalra S, Xu J, Pan YX, Pintar J, Kivell BM, Pasternak GW, Cameron MD, McLaughlin JP, Sames D, Majumdar S..  (2021)  Oxidative Metabolism as a Modulator of Kratom's Biological Actions.,  64  (22.0): [PMID:34783240] [10.1021/acs.jmedchem.1c01111]

Source

Source(1):

• Scientific Literature