Paynantheine

ID: ALA4848517

Chembl Id: CHEMBL4848517

Cas Number: 1346-36-7

PubChem CID: 3037629

Max Phase: Preclinical

Molecular Formula: C23H28N2O4

Molecular Weight: 396.49

Molecule Type: Unknown

Names and Identifiers

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

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/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13+/t14-,16-,19-/m0/s1

Standard InChI Key:  JGZKIGWXPPFMRG-CYSPOEIOSA-N

Alternative Forms

1. Parent:

   

   ALA4848517

   Paynantheine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 396.49

Molecular Weight (Monoisotopic): 396.2049

AlogP: 3.60

#Rotatable Bonds: 5

Polar Surface Area: 63.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.90

CX LogP: 3.00

CX LogD: 2.88

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: 1.63

References

1. Chear NJ, León F, Sharma A, Kanumuri SRR, Zwolinski G, Abboud KA, Singh D, Restrepo LF, Patel A, Hiranita T, Ramanathan S, Hampson AJ, McMahon LR, McCurdy CR..  (2021)  Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors.,  84  (4.0): [PMID:33635670] [10.1021/acs.jnatprod.0c01055]

2. Kamble SH, Berthold EC, King TI, Raju Kanumuri SR, Popa R, Herting JR, León F, Sharma A, McMahon LR, Avery BA, McCurdy CR..  (2021)  Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.,  84  (4.0): [PMID:33620222] [10.1021/acs.jnatprod.0c01163]

3. 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]

4. Smith MT, Kong D, Kuo A, Imam MZ, Williams CM..  (2022)  Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.,  65  (3.0): [PMID:34995453] [10.1021/acs.jmedchem.0c01915]

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