Classification Term: 168445

Germacrane sesquiterpenoids [PR010309] (ontology term: ad63afd085919b0de4be881b7b3b3472)

Germacrane sesquiterpenoids [PR010309]

found 36 associated metabolites at molecular_framework metabolite taxonomy ontology rank level.

Ancestor: C15 isoprenoids (sesquiterpenes) [PR0103]

Child Taxonomies: There is no child term of current ontology term.

Parthenolide

(1aR,4E,7aS,10aS,10bS)-1a,5-Dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one

C15H20O3 (248.14123700000002)


D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents (1Ar,7aS,10aS,10bS)-1a,5-dimethyl-8-methylidene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one is a germacranolide. Parthenolide has been used in trials studying the diagnostic of Allergic Contact Dermatitis. (1aR,7aS,10aS,10bS)-1a,5-dimethyl-8-methylidene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one is a natural product found in Cyathocline purpurea, Tanacetum parthenium, and other organisms with data available. Parthenolide belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Thus, parthenolide is considered to be an isoprenoid lipid molecule. Parthenolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Parthenolide is a bitter tasting compound found in sweet bay, which makes parthenolide a potential biomarker for the consumption of this food product. Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named. It is found in highest concentration in the flowers and fruit . relative retention time with respect to 9-anthracene Carboxylic Acid is 1.002 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.000 Parthenolide is a sesquiterpene lactone found in the medicinal herb Feverfew. Parthenolide exhibits anti-inflammatory activity by inhibiting NF-κB activation; also inhibits HDAC1 protein without affecting other class I/II HDACs. Parthenolide is a sesquiterpene lactone found in the medicinal herb Feverfew. Parthenolide exhibits anti-inflammatory activity by inhibiting NF-κB activation; also inhibits HDAC1 protein without affecting other class I/II HDACs.

   

Deoxyelephantopin

[(3S,4R,8R,9E,12R)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.04,8]pentadeca-1(15),9-dien-3-yl] 2-methylprop-2-enoate

C19H20O6 (344.125982)


Deoxyelephantopin is a sesquiterpenoid. Deoxyelephantopin is a natural product found in Elephantopus scaber with data available. Isodeoxyelephantopin is a terpene lactone. Deoxyelephantopin, a natural bioactive sesquiterpene lactone from Elephantopus scaber, has shown promising anticancer effects against a broad spectrum of cancers. Deoxyelephantopin inhibits NF-κB, MAPK, PI3K/Akt, and β-catenin signaling[1]. Deoxyelephantopin, a natural bioactive sesquiterpene lactone from Elephantopus scaber, has shown promising anticancer effects against a broad spectrum of cancers. Deoxyelephantopin inhibits NF-κB, MAPK, PI3K/Akt, and β-catenin signaling[1].

   

alatolide

[(1R,2R,4E,8E,10R)-4,8-bis(hydroxymethyl)-13-methylidene-12-oxo-11-oxabicyclo[8.3.0]trideca-4,8-dien-2-yl] 2-methylpropanoate

C19H26O6 (350.1729296)


A germacrane sesquiterpenoid laactone obtained by formal condensation of the carboxy group of isobutyric acid with the secondary hydroxy group of trihydroxygermaeranolide.

   

germacradienol

2-[(1R,2E,4S,7E)-4,8-dimethylcyclodeca-2,7-dien-1-yl]propan-2-ol

C15H26O (222.1983546)


   
   

Germacrene A

1,5-Cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-, (1E,5Z,8S)-

C15H24 (204.18779039999998)


   

Elephantopin

2-Propenoic acid,2-methyl-,(1aR,3R,8S,8aR,11aS,11bR)-1a,2,3,7,8,8a,9,10,11a,11b-decahydro-1a-methyl-9-methylene-5,10-dioxo-5H-3,6-methenofuro[2,3-f]oxireno[d]oxacycloundecin-8-ylester

C19H20O7 (360.120897)


   

Germacrene B

(1E,5E)-1,5-dimethyl-8-(propan-2-ylidene)cyclodeca-1,5-diene

C15H24 (204.18779039999998)


   

(±)-Geosmin

(4R,4aR,8aS)-4,8a-dimethyloctahydronaphthalen-4a(2H)-ol

C12H22O (182.1670562)


   

(1E,4Z)-germacrene B

(1E,4Z)-germacra-1(10),4,7(11)-triene (1E,5Z)-1,5-dimethyl-8-(propan-2-ylidene)cyclodeca-1,5-diene

C15H24 (204.18779039999998)


A germacrene B with a (1E,4Z)-configuration.

   

(1Z,4Z)-germacrene B

(1Z,4Z)-germacra-1(10),4,7(11)-triene (1Z,5Z)-1,5-dimethyl-8-(propan-2-ylidene)cyclodeca-1,5-diene

C15H24 (204.18779039999998)


   

(1Z,4E)-germacrene B

(1Z,4E)-germacra-1(10),4,7(11)-triene (1Z,5E)-1,5-dimethyl-8-(propan-2-ylidene)cyclodeca-1,5-diene

C15H24 (204.18779039999998)


   

Isoonopordopicrin

Isoonopordopicrin

C19H24O6 (348.1572804)


   
   
   

Elephantopinolide A

Elephantopinolide A

C19H20O7 (360.120897)


   

Elephantopinolide B

Elephantopinolide B

C20H22O7 (374.1365462)


   

Elephantopinolide D

Elephantopinolide D

C20H22O7 (374.1365462)


   

Elephantopinolide C

Elephantopinolide C

C19H20O7 (360.120897)


   

Elephantopinolide E

Elephantopinolide E

C20H22O7 (374.1365462)


   

Elephantopinolide F

Elephantopinolide F

C19H22O6 (346.1416312)


   

Elephantopinolide G

Elephantopinolide G

C20H22O7 (374.1365462)


   

Elephantopinolide H

Elephantopinolide H

C20H22O7 (374.1365462)


   

Elephantopinolide I

Elephantopinolide I

C19H20O7 (360.120897)


   

Elephantopinolide J

Elephantopinolide J

C19H20O7 (360.120897)


   
   

Elephantopinolide L

Elephantopinolide L

C15H18O5 (278.1154178)


   

Elephantopinolide M

Elephantopinolide M

C15H16O5 (276.0997686)


   

Elephantopinolide N

Elephantopinolide N

C21H26O7 (390.1678446)


   

Elephantopinolide O

Elephantopinolide O

C21H26O7 (390.1678446)


   

Elephantopinolide P

Elephantopinolide P

C20H24O7 (376.1521954)


   

9beta-hydroxy-11beta,13-dihydro-parthenolide-9-O-beta-D-glucopyranoside

9beta-hydroxy-11beta,13-dihydro-parthenolide-9-O-beta-D-glucopyranoside

C21H32O9 (428.2046222)


   

9alpha-hydroxy-11beta,13-dihydro-parthenolide-9-O-beta-D-glucopyranoside

9alpha-hydroxy-11beta,13-dihydro-parthenolide-9-O-beta-D-glucopyranoside

C21H32O9 (428.2046222)


   

1,10-epoxydeltoidin A

1,10-epoxydeltoidin A

C19H26O6 (350.1729296)


   
   

15-hydroxydeltoidin A

15-hydroxydeltoidin A

C19H26O6 (350.1729296)