Fumigaclavine C - Misplaced Pages

Fumigaclavine C
Names

IUPAC name quinoline-10-yl] acetate
Other names SM-1; (8β,9β)-2-(1,1-Dimethyl-2-propenyl)-6,8-dimethylergolin-9-ol acetate
Identifiers
CAS Number	62867-47-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:64673
ChemSpider	151750
KEGG	C20438
PubChem CID	173878
CompTox Dashboard (EPA)	DTXSID60978599
InChI InChI=1S/C23H30N2O2/c1-7-23(4,5)22-16-11-18-20(15-9-8-10-17(24-22)19(15)16)21(27-14(3)26)13(2)12-25(18)6/h7-10,13,18,20-21,24H,1,11-12H2,2-6H3/t13-,18+,20?,21-/m0/s1Key: OSICWVVWEXKSBD-HXLPLIFYSA-N
SMILES C1CN(2CC3=C(NC4=CC=CC(=C34)C21OC(=O)C)C(C)(C)C=C)C
Properties
Chemical formula	C₂₃H₃₀N₂O₂
Molar mass	366.505 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Fumigaclavine C is an ergoline alkaloid produced by Aspergillus fumigatus.

Both 8α and 8β diastereomers (epimers) were named fumigaclavine C in scientific literature.

References

Ma, HY; Song, YC; Mao, YY; Jiang, JH; Tan, RX; Luo, L (2006). "Endophytic fungal metabolite fumigaclavine C causes relaxation of isolated rat aortic rings". Planta Medica. 72 (5): 387–92. doi:10.1055/s-2005-916235. PMID 16557450.
Wallwey, Christiane; Li, Shu-Ming (2011-03-01). "Ergot alkaloids: structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes". Natural Product Reports. 28 (3): 496–510. doi:10.1039/C0NP00060D. ISSN 1460-4752. PMID 21186384.

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD (lysergide) LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine Brazergoline Cianergoline CY-208,243 Delergotrile Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

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