3-Dehydromitragynine; (2S,3S)-2((E)-1,3-Dimethoxy-3-oxoprop-1-en-2-yl)-3-ethyl-8-methoxy-2,3,4,6,7,12-hexahydro-1H-indolo[2,3-a]quinolizine-5-ium

ID: ALA5276728

Chembl Id: CHEMBL5276728

Max Phase: Preclinical

Molecular Formula: C23H29N2O4+

Molecular Weight: 397.50

Names and Identifiers

Canonical SMILES:  CC[C@@H]1C[N+]2=C(C[C@@H]1/C(=C\OC)C(=O)OC)c1[nH]c3cccc(OC)c3c1CC2

Standard InChI:  InChI=1S/C23H28N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16H,5,9-12H2,1-4H3/p+1/b17-13+/t14-,16+/m1/s1

Standard InChI Key:  LRKSTCBIGUUOED-DCHMLSIZSA-O

Alternative Forms

1. Parent:

   

   ALA5276728

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 397.50

Molecular Weight (Monoisotopic): 397.2122

AlogP: 3.28

#Rotatable Bonds: 5

Polar Surface Area: 63.56

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: ┄

CX LogP: -0.60

CX LogD: -0.60

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: 1.32

References

1. 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