9-Deacetoxyfumigaclavine C - Misplaced Pages

9-Deacetoxyfumigaclavine C
Names

IUPAC name 6,8β-Dimethyl-2-(2-methylbut-3-en-2-yl)ergoline
Systematic IUPAC name (6aR,9R,10aR)-7,9-Dimethyl-5-(2-methylbut-3-en-2-yl)-4,6,6a,7,8,9,10,10a-octahydroindoloquinoline
Identifiers
CAS Number	1137244-08-6
3D model (JSmol)	Interactive image
ChemSpider	24626669
PubChem CID	44715304
InChI InChI=1S/C21H28N2/c1-6-21(3,4)20-16-11-18-15(10-13(2)12-23(18)5)14-8-7-9-17(22-20)19(14)16/h6-9,13,15,18,22H,1,10-12H2,2-5H3/t13-,15-,18-/m1/s1Key: GXEMWNLJOIOIIM-DDUZABMNSA-N
SMILES 12CC3=C(NC4=C3C(=CC=C4)1()C(C)CN2C)C(C)(C)C=C
Properties
Chemical formula	C₂₁H₂₈N₂
Molar mass	308.469 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

9-Deacetoxyfumigaclavine C is an ergoline alkaloid. It is a potent, selective, anticancer compound, with in vitro activity comparable to doxorubicin (IC₅₀ = 3.1 μM against K562). 9-Deacetoxyfumigaclavine C is a compound made by a variety of fungi.

References

"KNApSAcK Metabolite Information - C00047370". www.knapsackfamily.com.
Ge HM; Yu ZG; Zhang J; Wu JH; Tan RX (2009). "Bioactive alkaloids from endophytic Aspergillus fumigatus". J Nat Prod. 72 (4): 753–5. doi:10.1021/np800700e. PMID 19256529.

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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