11-Methoxyuncarine C - CAS 61665-08-5
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Molecular Formula:
C18H19NO4
Molecular Weight:
398.459
COA:
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Chemical Family:
Alkaloids
Description:
11-Methoxyuncarine C is an alkaloid isolated from Uncaria rhynchophylla.
Appearance:
Powder
Synonyms:
Reserpinine oxindole; methyl (1S,4aS,5aS,6R,10aS)-6'-methoxy-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate
MSDS:
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InChIKey:
SRKHGHLMEDVZRX-XZLQSYOBSA-N
InChI:
InChI=1S/C22H26N2O5/c1-12-15-10-24-7-6-22(17-5-4-13(27-2)8-18(17)23-21(22)26)19(24)9-14(15)16(11-29-12)20(25)28-3/h4-5,8,11-12,14-15,19H,6-7,9-10H2,1-3H3,(H,23,26)/t12-,14-,15-,19-,22+/m0/s1
Canonical SMILES:
CC1C2CN3CCC4(C3CC2C(=CO1)C(=O)OC)C5=C(C=C(C=C5)OC)NC4=O
1.Two stereoisomeric pentacyclic oxindole alkaloids from Uncaria tomentosa: uncarine C and uncarine E.
Muhammad I1, Khan IA, Fischer NH, Fronczek FR. Acta Crystallogr C. 2001 Apr;57(Pt 4):480-2.
The chloroform solvate of uncarine C (pteropodine), (1'S,3R,4'aS,5'aS,10'aS)-1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxospiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid methyl ester, C(21)H(24)N(2)O(4).CHCl(3), has an absolute configuration with the spiro C atom in the R configuration. Its epimer at the spiro C atom, uncarine E (isopteropodine), (1'S,3S,4'aS,5'aS,10'aS)-1,2,5',5'a,7',8',10',10'a-octahydro-1'-methyl-2-oxospiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid methyl ester, C(21)H(24)N(2)O(4), has Z' = 3, with no solvent. Both form intermolecular hydrogen bonds involving only the oxindole, with N.O distances in the range 2.759 (4)-2.894 (5) A.
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CAS 61665-08-5 11-Methoxyuncarine C

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