Structure via PubChem · Public domain (PubChem)
Michellamine
Sign in to saveMichellamines are a group of atropisomeric alkaloid which have been found to be HIV viral replication inhibitors in vitro. It was discovered in the leaves of Ancistrocladus korupensis. There are three michellamines represented as A, B, and C; however, michellamine B is the most active against the NID-DZ strain of HIV-2.
Chemical data
- Formula
- C46H48N2O8
- Molecular weight
- 756.9 g/mol
- IUPAC name
- (1R,3R)-5-[3-[4-[(1R,3R)-6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-1-hydroxy-8-methoxy-6-methylnaphthalen-2-yl]-4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
- SMILES
- C[C@@H]1CC2=C(C(=CC(=C2[C@H](N1)C)O)O)C3=CC(=C(C4=C3C=C(C=C4OC)C)O)C5=C(C6=C(C=C(C=C6OC)C)C(=C5)C7=C8C[C@H](N[C@@H](C8=C(C=C7O)O)C)C)O
- InChIKey
- GMLBVLXDRNJFGR-MOUTVQLLSA-N
- XLogP
- 8.3
- Polar surface area
- 164 Ų
- H-bond donors
- 8
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- isoquinoline alkaloid
- Mass
- 756.341067
Show 4 more facts
- chemical formula
- C₄₆H₄₈N₂O₈
- canonical SMILES
- CC1CC2=C(C(=CC(=C2C(N1)C)O)O)C3=CC(=C(C4=C(C=C(C=C34)C)OC)O)C5=C(C6=C(C=C(C=C6C(=C5)C7=C8CC(NC(C8=C(C=C7O)O)C)C)C)OC)O
- isomeric SMILES
- C[C@@H]1CC2=C(C(=CC(=C2[C@H](N1)C)O)O)C3=CC(=C(C4=C(C=C(C=C34)C)OC)O)C5=C(C6=C(C=C(C=C6C(=C5)C7=C8C[C@H](N[C@@H](C8=C(C=C7O)O)C)C)C)OC)O
- found in taxon
- Triphyophyllum peltatum
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Occurrence
- Synthesis
- Research
- References
Michellamines are a group of atropisomeric alkaloid which have been found to be HIV viral replication inhibitors in vitro. It was discovered in the leaves of Ancistrocladus korupensis. There are three michellamines represented as A, B, and C; however, michellamine B is the most active against the NID-DZ strain of HIV-2.
==Occurrence== Michellamine A and B occur naturally in Ancistrocladus korupensis leaves. Other chemical substances including alkaloids, tannins, and saponins are found in the roots, leaves, stems, flowers, or bark.
Excerpted from Wikipedia’s “Michellamine” article, available under the CC BY-SA 4.0 licence.