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

ID: ALA292521

Chembl Id: CHEMBL292521

Cas Number: 425623-55-8

PubChem CID: 10927114

Max Phase: Preclinical

Molecular Formula: C22H28N2O4

Molecular Weight: 384.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H]1CN2CCc3c([nH]c4cccc(O)c34)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

Standard InChI:  InChI=1S/C22H28N2O4/c1-4-13-11-24-9-8-14-20-17(6-5-7-19(20)25)23-21(14)18(24)10-15(13)16(12-27-2)22(26)28-3/h5-7,12-13,15,18,23,25H,4,8-11H2,1-3H3/b16-12+/t13-,15+,18+/m1/s1

Standard InChI Key:  IIRZCWUQUBSIPF-XZNUVMSOSA-N

Alternative Forms

1. Parent:

   

   ALA292521

   9-O-Demethylmitragynine

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: 384.48

Molecular Weight (Monoisotopic): 384.2049

AlogP: 3.52

#Rotatable Bonds: 4

Polar Surface Area: 74.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.18

CX Basic pKa: 7.04

CX LogP: 3.15

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: 1.71

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. Raffa RB, Beckett JR, Brahmbhatt VN, Ebinger TM, Fabian CA, Nixon JR, Orlando ST, Rana CA, Tejani AH, Tomazic RJ..  (2013)  Orally active opioid compounds from a non-poppy source.,  56  (12): [PMID:23517479] [10.1021/jm400143z]

3. Obeng S, Kamble SH, Reeves ME, Restrepo LF, Patel A, Behnke M, Chear NJ, Ramanathan S, Sharma A, León F, Hiranita T, Avery BA, McMahon LR, McCurdy CR..  (2020)  Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.,  63  (1): [PMID:31834797] [10.1021/acs.jmedchem.9b01465]

4. León F, Obeng S, Mottinelli M, Chen Y, King TI, Berthold EC, Kamble SH, Restrepo LF, Patel A, Gamez-Jimenez LR, Lopera-Londoño C, Hiranita T, Sharma A, Hampson AJ, Canal CE, McMahon LR, McCurdy CR..  (2021)  Activity of Mitragyna speciosa ("Kratom") Alkaloids at Serotonin Receptors.,  64  (18.0): [PMID:34467758] [10.1021/acs.jmedchem.1c00726]

5. 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