Helenium amarum, also known as yellowdicks, yellow sneezeweed, fiveleaf sneezeweed, and bitter sneezeweed, is an annual herb in the daisy family. It is native to the south-central United States and northern Mexico, but has also been introduced to other parts of North America, Australia, and the West Indies. This bushy plant can grow up to 70 centimeters tall and has narrow leaves and daisy-like flower heads with yellow disc and ray florets. It produces small fruit and is considered a weedy plant in some areas. Helenium amarum contains a toxic compound called tenulin, making it harmful to mammals and insects.

Synonyms Top

Scientific name	Authority	First published in
Heleniastrum tenuifolium	(Nutt.) Kuntze	Revis. Gen. Pl. 1: 342 (1891)
Gaillardia amara	Raf.	Fl. Ludov. : 69 (1817)
Helenium tenuifolium	Nutt.	J. Acad. Nat. Sci. Philadelphia vii. (1834) 66.

Common names Top

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Filter by language:

Language	Common/alternative name
English	yellowdicks
Persian	گل راسن تلخ
Chinese	苦味堆心菊

Subspecies (abbr. subsp./ssp.) Top

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No subspecies added yet.

Varieties (abbr. var.) Top

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Name	Authority	First published in
Helenium amarum var. badium	(A.Gray) Waterf.	Rhodora 62: 321 (1960)

Subvarieties (abbr. subvar.) Top

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No subvariety added yet.

Forms (abbr. f.) Top

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No forms added yet.

Germination/Propagation Top

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Sow seeds at 20°C, expecting germination within 3 months without further temperature treatment.

Requires Light or Surface Sowing: These seeds need light to germinate and should not be covered with soil or only very lightly. They are often very small and sown directly on the surface of the growing medium.

Distribution (via POWO/KEW) Top

Legend for the distribution data:

- Doubtful data

- Extinct

- Introduced

- Native

Asia-tropical click to expand
- Indo-China
  - Myanmar
- Malesia
  - Jawa

Australasia click to expand
- Australia
  - Queensland

Northern America click to expand
- Mexico
  - Mexico Northeast
- North-central U.S.A.
  - Kansas
  - Missouri
  - Oklahoma
  - Wisconsin
- Northeastern U.S.A.
  - Indiana
  - Michigan
  - New York
  - Pennsylvania
- South-central U.S.A.
  - Texas
- Southeastern U.S.A.
  - Alabama
  - Arkansas
  - District Of Columbia
  - Florida
  - Georgia
  - Louisiana
  - Mississippi
  - North Carolina
  - South Carolina
  - Tennessee
  - Virginia
- Southwestern U.S.A.
  - California

Southern America click to expand
- Caribbean
  - Cayman Islands
  - Dominican Republic
  - Trinidad-Tobago

Links to other databases Top

Suggest others/fix!

Database	ID/link to page
World Flora Online	wfo-0000075426
Florida Plant Atlas	2883
Flora of Alabama	776
USDA Plants	HEAM
Tropicos	2700849
Flora of Italy	11855
KEW	urn:lsid:ipni.org:names:118685-2
Missouri Botanical Garden	277197
PFAF	Helenium amarum
Open Tree Of Life	1062344
Observations.org	211510
NCBI Taxonomy	289417
Nature Serve	2.145025
IPNI	118685-2
iNaturalist	77348
GBIF	5401836
Freebase	/m/03ydyc5
EPPO	HENAM
Calflora (Californian flora)	4025
USDA GRIN	104272
Wikipedia	Helenium_amarum
CMAUP	NPO18919

Genomes (via NCBI) Top

No reference genome is available on NCBI yet. We are constantly monitoring for new data.

Scientific Literature Top

Below are displayed the latest 15 articles published in PMC (PubMed Central®) and other sources (DOI number only)!
If you wish to see all the related articles click here.

Title

Authors

Publication

Released

IDs

Sesquiterpene Lactones Attenuate Paclitaxel Resistance Via Inhibiting MALAT1/STAT3/ FUT4 Axis and P-Glycoprotein Transporters in Lung Cancer Cells

Ding Y, Zhen Z, Nisar MA, Ali F, Din RU, Khan M, Mughal TA, Alam G, Liu L, Saleem MZ

Front Pharmacol

24-Feb-2022

PMCID:	PMC8909900
doi:	10.3389/fphar.2022.795613
PMID:	35281907

Airborne environmental DNA metabarcoding detects more diversity, with less sampling effort, than a traditional plant community survey

Johnson MD, Fokar M, Cox RD, Barnes MA

BMC Ecol Evol

06-Dec-2021

PMCID:	PMC8647488
doi:	10.1186/s12862-021-01947-x
PMID:	34872490

A Mixed Infection of Helenium Virus S With Two Distinct Isolates of Butterbur Mosaic Virus, One of Which Has a Major Deletion in an Essential Gene

Hammond J, Reinsel M, Grinstead S, Lockhart B, Jordan R, Mollov D

Front Microbiol

21-Dec-2020

PMCID:	PMC7779399
doi:	10.3389/fmicb.2020.612936
PMID:	33408710

An initial industrial flora: A framework for botanical research in cooperation with industry for biodiversity conservation

Lucardi RD, Cunard CE, Hughes SC, Burgess KS, Reed JN, Whitehurst LE, Worthy SJ, Marsico TD

PLoS One

01-Apr-2020

PMCID:	PMC7112212
doi:	10.1371/journal.pone.0230729
PMID:	32236107

Tenulin and isotenulin inhibit P-glycoprotein function and overcome multidrug resistance in cancer cells

Chang YT, Wang CC, Wang JY, Lee TE, Cheng YY, Morris-Natschke SL, Lee KH, Hung CC

Phytomedicine

05-Sep-2018

PMCID:	PMC6421864
doi:	10.1016/j.phymed.2018.09.008
PMID:	30668405

Emerging Anti-Mitotic Activities and Other Bioactivities of Sesquiterpene Compounds upon Human Cells

Bosco A, Golsteyn RM

Molecules

13-Mar-2017

PMCID:	PMC6155193
doi:	10.3390/molecules22030459
PMID:	28335397

Germacrene A synthase in yarrow (Achillea millefolium) is an enzyme with mixed substrate specificity: gene cloning, functional characterization and expression analysis

Pazouki L, Memari HR, Kännaste A, Bichele R, Niinemets Ü

Front Plant Sci

03-Mar-2015

PMCID:	PMC4347605
doi:	10.3389/fpls.2015.00111
PMID:	25784918

Isotenulin

Knight KS, Smith CT, Waddell TG

Acta Crystallogr Sect E Struct Rep Online

20-Jul-2013

PMCID:	PMC3793783
doi:	10.1107/S1600536813019703
PMID:	24109370

Tenulin 0.25-hydrate, a sesquiterpene lactone isolated from Helenium amarum

Knight KS, Smith CT, Waddell TG, Noll B

Acta Crystallogr Sect E Struct Rep Online

10-Jul-2013

PMCID:	PMC3793741
doi:	10.1107/S1600536813018369
PMID:	24109328

Sesquiterpenoids Lactones: Benefits to Plants and People

Chadwick M, Trewin H, Gawthrop F, Wagstaff C

Int J Mol Sci

19-Jun-2013

PMCID:	PMC3709812
doi:	10.3390/ijms140612780
PMID:	23783276

A revision of the Megachile subgenus Litomegachile Mitchell with an illustrated key and description of a new species (Hymenoptera, Megachilidae, Megachilini)

Bzdyk EL

Zookeys

13-Sep-2012

PMCID:	PMC3487634
doi:	10.3897/zookeys.221.3234
PMID:	23129980

Constituents of Helenium amarum (Compositae). I. X-Ray Crystallographic Determination of Heleniamarin, a New Sesquiterpene Lactone.

Tor Ottersen, Ulla Sørensen, Mahmoud A. Elsohly, Carlton E. Turner, Curt R. Enzell, Jan-Erik Berg, Anne-Marie Pilotti

Danish Chemical Society

19-Jun-2008

doi:	10.3891/ACTA.CHEM.SCAND.32B-0079

Toxicological evaluation of a chicory root extract

Schmidt BM, Ilic N, Poulev A, Raskin I

Food Chem Toxicol

11-Jan-2007

PMCID:	PMC3836359
doi:	10.1016/j.fct.2006.12.019
PMID:	17306431

Constituents of Helenium amarum. III. Isolation and Characterization of Iso-Heleniamarin, a New Sesquiterpene Lactone

Mahmoud A. ElSohly, Alpana S. Sharma, Carlton E. Turner

American Chemical Society (ACS)

17-Mar-2005

doi:	10.1021/NP50017A023

Constituents of Helenium amarum. II. Isolation and Characterization of Heleniamarin and Other Constituents

Mahmoud A. Elsohly, John C. Craig, Carlton E. Turner, Alpana S. Sharma

American Chemical Society (ACS)

17-Mar-2005

doi:	10.1021/NP50005A002

Phytochemical Profile Top

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Below are displayed the proven (via scientific papers) natural compounds!
You can also contribute to this by clicking here.

Name	PubChem ID	Canonical SMILES	MW	Found in	Proof
> Benzenoids / Benzene and substituted derivatives / Benzoic acids and derivatives / Acylaminobenzoic acid and derivatives
Antimycin A19	56600064	Click to see CCCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)C(C)C(C)C	548.60	unknown	via CMAUP database
Antimycin A20	54764156	Click to see CCCCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)C	506.50	unknown	via CMAUP database
Antimycin A2a	447434	Click to see CCCCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)C(C)C	534.60	unknown	via CMAUP database
Antimycin A3	245869	Click to see CCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CC(C)C	520.60	unknown	via CMAUP database
Antimycin A3a 2'R-epimer	86278330	Click to see CCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)C(C)CC	520.60	unknown	via CMAUP database
Benzoic acid, 3-(formylamino)-2-hydroxy-	15409159	Click to see C1=CC(=C(C(=C1)NC=O)O)C(=O)O	181.15	unknown	via CMAUP database
> Benzenoids / Benzene and substituted derivatives / Benzoic acids and derivatives / Hydroxybenzoic acid derivatives
4-Methyl-3-hydroxyanthranilic acid	95222	Click to see CC1=C(C(=C(C=C1)C(=O)O)N)O	167.16	unknown	via CMAUP database
> Lipids and lipid-like molecules / Fatty Acyls / Fatty alcohols
Virginiae butanolide A	10036830	Click to see CC(C)CCCC(C1C(COC1=O)CO)O	230.30	unknown	via CMAUP database
> Lipids and lipid-like molecules / Prenol lipids / Terpene glycosides
[(1S,2S,3R,5S,6R,8S)-6-hydroxy-8-methyl-3-[(2R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl 4-hydroxybenzoate	137704782	Click to see CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC=C(C=C5)O)OC6C(C(C(C(O6)CO)O)O)O)O	496.50	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones
Amaralin	100302	Click to see CC1CC2C(CC3(C1C4C(C3O)O4)C)C(=C)C(=O)O2	264.32	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1 https://doi.org/10.1021/NP50005A002
Amaralin from helenium amarum	323623	Click to see CC1CC2C(CC3(C1C4C(C3O)O4)C)C(=C)C(=O)O2	264.32	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones / Sesquiterpene lactones
(14-Hydroxy-1,9-dimethyl-4-methylidene-5-oxo-6,12-dioxatetracyclo[8.4.0.03,7.011,13]tetradecan-2-yl) acetate	162965037	Click to see CC1CC2C(C(C3(C1C4C(C3O)O4)C)OC(=O)C)C(=C)C(=O)O2	322.40	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
(1R,2R,6S,7R,9S,12R,15R)-13-hydroxy-2,7,12,13-tetramethyl-10,14-dioxatetracyclo[7.5.1.02,6.012,15]pentadec-4-ene-3,11-dione	16745514	Click to see CC1CC2C3C(C4(C1C=CC4=O)C)OC(C3(C(=O)O2)C)(C)O	306.40	unknown	via CMAUP database
(1R,2R,7R,9S,12R,13S,15R)-13-hydroxy-2,7,12,13-tetramethyl-10,14-dioxatetracyclo[7.5.1.02,6.012,15]pentadec-5-ene-3,11-dione	101316958	Click to see CC1CC2C3C(C4(C1=CCC4=O)C)OC(C3(C(=O)O2)C)(C)O	306.40	unknown	https://doi.org/10.3891/ACTA.CHEM.SCAND.32B-0079
(1S,2R,6S,7S,9R,12R,15R)-13-hydroxy-2,7,12,13-tetramethyl-10,14-dioxatetracyclo[7.5.1.02,6.012,15]pentadec-4-ene-3,11-dione	131676088	Click to see CC1CC2C3C(C4(C1C=CC4=O)C)OC(C3(C(=O)O2)C)(C)O	306.40	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1 https://doi.org/10.1021/JF00078A010 https://doi.org/10.1021/NP50052A019 https://doi.org/10.1021/JF60201A012 https://doi.org/10.1021/NP50005A002
(2R,9S,13S)-13-hydroxy-2,7,12,13-tetramethyl-10,14-dioxatetracyclo[7.5.1.02,6.012,15]pentadec-5-ene-3,11-dione	5317984	Click to see CC1CC2C3C(C4(C1=CCC4=O)C)OC(C3(C(=O)O2)C)(C)O	306.40	unknown	https://doi.org/10.3891/ACTA.CHEM.SCAND.32B-0079 https://doi.org/10.1021/NP50005A002
(3aR,5R,5aR,8aR,9R,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione	44398510	Click to see CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2	262.30	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
[(1S,2R,3R,7S,9R,10S,11R,13S,14R)-14-hydroxy-1,9-dimethyl-4-methylidene-5-oxo-6,12-dioxatetracyclo[8.4.0.03,7.011,13]tetradecan-2-yl] acetate	162965038	Click to see CC1CC2C(C(C3(C1C4C(C3O)O4)C)OC(=O)C)C(=C)C(=O)O2	322.40	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
Balduilin	23332	Click to see CC1CC2C(C(C3(C1C=CC3=O)C)OC(=O)C)C(=C)C(=O)O2	304.34	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
Helenalin	23205	Click to see CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2	262.30	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
Heleniamarin	3085349	Click to see CC1CC2C3C(C4(C1=CCC4=O)C)OC(C3(C(=O)O2)C)(C)O	306.40	unknown	https://doi.org/10.1021/NP50005A002
Isoheleniamarin	6455209	Click to see CC1CC2C(C(C(=O)O2)C)C(C3(C1=CCC3=O)C)OC(=O)C	306.40	unknown	https://doi.org/10.1021/NP50017A023
Mexicanin I	93016	Click to see CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2	262.30	unknown	https://doi.org/10.1021/NP50005A002
Sample A of helenalin	52167	Click to see CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2	262.30	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
Tenulin	227830	Click to see CC1CC2C3C(C4(C1C=CC4=O)C)OC(C3(C(=O)O2)C)(C)O	306.40	unknown	https://doi.org/10.1021/JF00078A010 https://doi.org/10.1021/NP50005A002 https://doi.org/10.1021/JF60201A012 https://doi.org/10.1021/NP50052A019 https://doi.org/10.1016/S0031-9422(00)81123-1
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones / Sesquiterpene lactones / Ambrosanolides and secoambrosanolides
Aromaticin	282529	Click to see CC1CC2C(CC3(C1C=CC3=O)C)C(=C)C(=O)O2	246.30	unknown	https://doi.org/10.1021/NP50005A002 https://doi.org/10.1016/S0031-9422(00)81123-1
> Lipids and lipid-like molecules / Prenol lipids / Terpene lactones / Sesquiterpene lactones / Guaianolides and derivatives
(3aR,5aS,8R,8aR,9aR)-5,8-dimethyl-1-methylidene-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-5a,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one	162875009	Click to see CC1=CC2C(CC3C1CCC3(C)OC4C(C(C(CO4)O)O)O)C(=C)C(=O)O2	380.40	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
(3aS,5aS,8R,8aR,9aR)-5,8-dimethyl-1-methylidene-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-5a,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one	162875008	Click to see CC1=CC2C(CC3C1CCC3(C)OC4C(C(C(CO4)O)O)O)C(=C)C(=O)O2	380.40	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
[(2S,3R,4S,5S)-2-[[(3aR,5aS,8R,8aR,9aR)-8-methyl-1,5-dimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-yl]oxy]-4,5-dihydroxyoxan-3-yl] acetate	162921700	Click to see CC(=O)OC1C(C(COC1OC2(CCC3C2CC4C(CC3=C)OC(=O)C4=C)C)O)O	422.50	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
2-Desoxyflorilenalin-L-\|A-arabinopyranoside	162922339	Click to see CC1(CCC2C1CC3C(CC2=C)OC(=O)C3=C)OC4C(C(C(CO4)O)O)O	380.40	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
2-Desoxypleniradin-L-\|A-arabinopyranoside, 2-acetate	162921701	Click to see CC(=O)OC1C(C(COC1OC2(CCC3C2CC4C(CC3=C)OC(=O)C4=C)C)O)O	422.50	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
4,5-Dihydroxy-2-((5-methyl-3,8-dimethylene-2-oxododecahydroazuleno[6,5-b]furan-5-yl)oxy)tetrahydro-2H-pyran-3-yl acetate	162921699	Click to see CC(=O)OC1C(C(COC1OC2(CCC3C2CC4C(CC3=C)OC(=O)C4=C)C)O)O	422.50	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
5,8-dimethyl-1-methylidene-8-(3,4,5-trihydroxyoxan-2-yl)oxy-5a,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one	162875007	Click to see CC1=CC2C(CC3C1CCC3(C)OC4C(C(C(CO4)O)O)O)C(=C)C(=O)O2	380.40	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
8-Methyl-1,5-dimethylidene-8-(3,4,5-trihydroxyoxan-2-yl)oxy-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one	162922338	Click to see CC1(CCC2C1CC3C(CC2=C)OC(=O)C3=C)OC4C(C(C(CO4)O)O)O	380.40	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
Florilenalin	442243	Click to see CC1(CC(C2C1CC3C(CC2=C)OC(=O)C3=C)O)O	264.32	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
> Lipids and lipid-like molecules / Prenol lipids / Tetraterpenoids / Carotenoids / Xanthophylls
[(1S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hexadecanoyloxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-yl] hexadecanoate	17751015	Click to see CCCCCCCCCCCCCCCC(=O)OC1CC(=C(C(C1)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2C(=CC(CC2(C)C)OC(=O)CCCCCCCCCCCCCCC)C)C)C)C	1045.70	unknown	via CMAUP database
> Organic acids and derivatives / Carboxylic acids and derivatives / Amino acids, peptides, and analogues / N-acyl-alpha amino acids and derivatives
antimycin A1	14957	Click to see CCCCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CC(C)C	548.60	unknown	via CMAUP database
> Organic acids and derivatives / Keto acids and derivatives / Alpha-keto acids and derivatives
Ketomycin	19489	Click to see C1CC(CC=C1)C(=O)C(=O)O	154.16	unknown	via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Aminosaccharides / Aminoglycosides
Oleandomycin	72493	Click to see CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)O)OC)C)C)C)O)C)C)O)N(C)C	687.90	unknown	via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Carbohydrates and carbohydrate conjugates / Glycosyl compounds / Glycosylamines
9-[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]-3H-purin-6-one	21785357	Click to see C1C(C(C(C(O1)N2C=NC3=C2NC=NC3=O)O)O)O	268.23	unknown	via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Carbonyl compounds / Aldehydes / Alpha-hydrogen aldehydes
4-[(1R,2S)-3,3-dimethyl-2-(3-oxobutyl)cyclobutyl]pent-4-enal	162912283	Click to see CC(=O)CCC1C(CC1(C)C)C(=C)CCC=O	236.35	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
4-[3,3-Dimethyl-2-(3-oxobutyl)cyclobutyl]pent-4-enal	89488063	Click to see CC(=O)CCC1C(CC1(C)C)C(=C)CCC=O	236.35	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
> Organic oxygen compounds / Organooxygen compounds / Carbonyl compounds / Aryl ketones / Aryl alkyl ketones
(alphaR,2R)-alpha,5alpha-Dimethyl-6alpha-[(1E,3E,5E,7E,9S)-1,9-diethyl-14-oxo-14-(1H-pyrrole-2-yl)-1,3,5,7-tetradecatetraenyl]tetrahydro-2H-pyran-2beta-acetic acid	101789368	Click to see CCC(CCCCC(=O)C1=CC=CN1)C=CC=CC=CC=C(CC)C2C(CCC(O2)C(C)C(=O)O)C	495.70	unknown	via CMAUP database
Indanomycin	10345604	Click to see CCC1CCC2C1C=CC(C2C(=O)C3=CC=CN3)C=CC=C(CC)C4C(CCC(O4)C(C)C(=O)O)C	493.70	unknown	via CMAUP database
> Organic oxygen compounds / Organooxygen compounds / Carbonyl compounds / Ketones
4-[(1S,4R)-4-(5-hydroxypent-1-en-2-yl)-2,2-dimethylcyclobutyl]butan-2-one	163071239	Click to see CC(=O)CCC1C(CC1(C)C)C(=C)CCCO	238.37	unknown	https://doi.org/10.1016/S0031-9422(00)81123-1
> Organoheterocyclic compounds / Benzopyrans / 1-benzopyrans / Pyranochromenes
(2R)-6',10-Dihydroxy-7',9'-dimethoxy-4',5',9-trioxo-4,4',5',9-tetrahydrospiro[benzo[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphtho[1,2-b]furan]-7-carboxylic acid methyl ester	97042233	Click to see COC1=CC(=C(C2=C1C3=C(CC4(O3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)C(=O)C2=O)O)OC	536.40	unknown	via CMAUP database
gamma-Rubromycin	5464075	Click to see COC1=CC(=O)C2=C(C1=O)C(=C3C(=C2O)CC4(O3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O	522.40	unknown	via CMAUP database
> Organoheterocyclic compounds / Diazanaphthalenes / Benzodiazines / Quinoxalines / Phenazines and derivatives
6-Acetylphenazine-1-carboxylic acid	443635	Click to see CC(=O)C1=C2C(=CC=C1)N=C3C(=N2)C=CC=C3C(=O)O	266.25	unknown	via CMAUP database
> Organoheterocyclic compounds / Imidazodiazepines
Pentostatin	439693	Click to see C1C(C(OC1N2C=NC3=C2NC=NCC3O)CO)O	268.27	unknown	via CMAUP database
Vira A deaminase inhibitor	44283251	Click to see C1C(C(OC1N2C=NC3=C2NC=NCC3O)CO)O	268.27	unknown	via CMAUP database
> Organoheterocyclic compounds / Lactones / Gamma butyrolactones
(3R,4R,5S)-3-hexyl-4-hydroxy-5-methyloxolan-2-one	11030843	Click to see CCCCCCC1C(C(OC1=O)C)O	200.27	unknown	via CMAUP database
> Organoheterocyclic compounds / Oxanes
(1S,3R,7S,9R,10S,11R,13S,14R)-14-hydroxy-1,9-dimethyl-6,12-dioxatetracyclo[8.4.0.03,7.011,13]tetradecan-5-one	44566392	Click to see CC1CC2C(CC(=O)O2)CC3(C1C4C(C3O)O4)C	252.31	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Anthracyclines
Cinerubin B	73593	Click to see CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C=CC(=C4C3=O)O)O)O)OC5CC(C(C(O5)C)OC6CC7C(C(O6)C)OC8C(O7)CC(=O)C(O8)C)N(C)C)O	825.80	unknown	via CMAUP database
> Phenylpropanoids and polyketides / Flavonoids / O-methylated flavonoids / 6-O-methylated flavonoids
Hispidulin	5281628	Click to see COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=C(C=C3)O)O	300.26	unknown	https://doi.org/10.1021/NP50005A002
> Phenylpropanoids and polyketides / Isoflavonoids / Rotenoids / Rotenones
(7aS)-13,13aalpha-Dihydro-7abeta-hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one	11962145	Click to see CC1(C=CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)C	410.40	unknown	via CMAUP database

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Helenium amarum

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