Compounds > skyrin
Page last updated: 2024-12-06

skyrin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Skyrin is a red pigment produced by the fungus Penicillium islandicum. It is a mycotoxin that is known to be toxic to animals and humans. Skyrin is a potent inhibitor of the enzyme cytochrome P450, which is involved in the metabolism of many drugs and other compounds. Skyrin has also been shown to have anticancer activity. Skyrin is studied for its potential to be used in the development of new drugs and therapies. It is also studied for its potential to be used as a bioindicator of fungal contamination in food and other materials.'

skyrin: main pigment of toxin rice fungus Penicillium islandicum; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID73071
CHEMBL ID472851
CHEBI ID144311
SCHEMBL ID2665352
MeSH IDM0053845

Synonyms (35)

Synonym
c30h18o10
NCI60_003292
nsc-361128
skyrin
NSC361128 ,
602-06-2
(1,1'-bianthracene)-9,9',10,10'-tetrone, 2,2',4,4',5,5'-hexahydroxy-7,7'-dimethyl-, (s)-
nsc 361128
ccris 4401
2,4,5-trihydroxy-7-methyl-1-(2,4,5-trihydroxy-7-methyl-9,10-dioxoanthracen-1-yl)anthracene-9,10-dione
CHEMBL472851 ,
CHEBI:144311
bdbm50388868
unii-vla1f42gxp
vla1f42gxp ,
SCHEMBL2665352
rhodophyscin
[1,1'-bianthracene]-9,9',10,10'-tetrone, 2,2',4,4',5,5'-hexahydroxy-7,7'-dimethyl-, (1s)
(+)-s-skyrin
1,1'-bi[anthryl-9,10-dione], 2,2',4,4',5,5'-hexahydroxy-7,7'-dimethyl-
endothianin
MQSXZQXHIJMNAF-UHFFFAOYSA-N
HB4088
skirin
DTXSID00208943
AKOS030532981
35144-94-6
2,2',4,4',5,5'-hexahydroxy-7,7'-dimethyl-[1,1'-bianthracene]-9,9',10,10'-tetraone
(s)-2,2',4,4',5,5'-hexahydroxy-7,7'-dimethyl-[1,1'-bianthracene]-9,9',10,10'-tetraone
131233-49-3
(r)-2,2',4,4',5,5'-hexahydroxy-7,7'-dimethyl-[1,1'-bianthracene]-9,9',10,10'-tetraone
Q27291883
(-)-r-skyrin
BS-1239
1,1'-bisemodin

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
biarylAn organic aromatic compound whose structure contains two aromatic rings or ring systems, joined to each other by a single bond.
trihydroxyanthraquinoneA member of the class of hydroxyanthraquinones carrying three hydroxy substituents.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Botulinum neurotoxin type A Clostridium botulinum A str. HallIC50 (µMol)31.50002.10002.10002.1000AID673914
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (63)

Assay IDTitleYearJournalArticle
AID360621Growth inhibition of human HeLa cells assessed as [3H]thymidine incorporation at 50 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360623Growth inhibition of human HeLa cells assessed as [3H]thymidine incorporation at 12.5 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID734248Cytotoxicity against mouse BALB/3T3 cells assessed as growth inhibition up to 32 ug/mL after 48 hrs by Alamar blue assay2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID734251Antibacterial activity against ceftazidime, ciprofloxacin, cefepime, gentamycin, imipenem, meropenem, piperacillin/tazobactam-resistant Pseudomonas aeruginosa 63230 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360636Growth inhibition of human Raji cells assessed as [3H]thymidine incorporation at 25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360617Growth inhibition of human Calu1 cells assessed as [3H]thymidine incorporation at 6.25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360616Growth inhibition of human Calu1 cells assessed as [3H]thymidine incorporation at 12.5 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID673912Inhibition of Clostridium botulinum Hall BoNT/A protease activity using Ac-SNKTRIDEANQRATKML-NH2 as substrate at 100 uM after 5 mins by RP-HPLC analysis2012ACS medicinal chemistry letters, May-10, Volume: 3, Issue:5
Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.
AID360638Growth inhibition of human Raji cells assessed as [3H]thymidine incorporation at 6.25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID673913Inhibition of Clostridium botulinum Hall BoNT/A protease activity using Ac-SNKTRIDEANQRATKML-NH2 as substrate at 20 uM after 5 mins by RP-HPLC analysis2012ACS medicinal chemistry letters, May-10, Volume: 3, Issue:5
Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.
AID360646Growth inhibition of african green monkey Vero cells assessed as [3H]thymidine incorporation at 3.125 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360652Growth inhibition of human WISH cells assessed as [3H]thymidine incorporation at 6.25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID734252Antibacterial activity against doxycycline-intermediate Streptococcus pyogenes 014327 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID734247Cytotoxicity against human THP1 cells assessed as growth inhibition up to 32 ug/mL after 48 hrs by Alamar blue assay2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID734246Antibacterial activity against Staphylococcus aureus ATCC 29213 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID733839Induction of liaI promoter in Bacillus subtilis IS34 promoter at 64 ug/mL after 3 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360615Growth inhibition of human Calu1 cells assessed as [3H]thymidine incorporation at 25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360629Growth inhibition of human K562 cells assessed as [3H]thymidine incorporation at 25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID734245Antibacterial activity against Staphylococcus aureus ATCC 29213 assessed as concentration required for partial growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID733848Antibacterial activity against clarithromycin, erythromycin, moxifloxacin, telithromycin, vancomycin-resistant Enterococcus faecalis UW 2689 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360635Growth inhibition of human Raji cells assessed as [3H]thymidine incorporation at 50 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360650Growth inhibition of human WISH cells assessed as [3H]thymidine incorporation at 25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360626Inhibition of human HeLa cell proliferation assessed as [3H]thymidine incorporation after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360653Growth inhibition of human WISH cells assessed as [3H]thymidine incorporation at 3.125 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360628Growth inhibition of human K562 cells assessed as [3H]thymidine incorporation at 50 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360645Growth inhibition of african green monkey Vero cells assessed as [3H]thymidine incorporation at 6.25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360624Growth inhibition of human HeLa cells assessed as [3H]thymidine incorporation at 6.25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360654Inhibition of human WISH cell proliferation assessed as [3H]thymidine incorporation after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360651Growth inhibition of human WISH cells assessed as [3H]thymidine incorporation at 12.5 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID733837Induction of bmrC promoter in Bacillus subtilis IS34 promoter at 64 ug/mL after 3 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID1666597Induction of DNA damage in human SU8686 cells assessed as increase in gammaH2AX phosphorylation at ser193 at cytotoxic IC50 in presence of 0.3 uM doxorubicin by fluorometry method2020Bioorganic & medicinal chemistry, 02-15, Volume: 28, Issue:4
Targeting the DNA damage response (DDR) by natural compounds.
AID360643Growth inhibition of african green monkey Vero cells assessed as [3H]thymidine incorporation at 25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID733847Antibacterial activity against clarithromycin, erythromycin, telithromycin, vancomycin-resistant Enterococcus faecium 6011 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID733850Antibacterial activity against Streptococcus pneumoniae ATCC 49619 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID733838Induction of helD promoter in Bacillus subtilis IS34 at 64 ug/mL after 3 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360631Growth inhibition of human K562 cells assessed as [3H]thymidine incorporation at 6.25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360619Growth inhibition of human Calu1 cells assessed as [3H]thymidine incorporation at 3.125 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID734253Antibacterial activity against ceftazidime, clarithromycin, ciprofloxacin, clindamycin, doxycycline, erythromycin, methicillin, moxifloxacin, kanamycin, telithromycin, rifampicin, methicillin-resistant, vancomycin-intermediate Staphylococcus aureus subsp.2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360644Growth inhibition of african green monkey Vero cells assessed as [3H]thymidine incorporation at 12.5 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID733843Antibacterial activity against doxycycline, kanamycin-resistant Klebsiella pneumoniae ATCC 27799 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID734243Antibacterial activity against amoxicillin, chloramphenicol, ciprofloxacin, clindamycin, erythromycin, fosmidomycin, gentamycin, kanamycin, nitrofurantoin, telithromycin, methicillin-resistant Staphylococcus aureus 25697 assessed as growth inhibition by C2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID733844Antibacterial activity against ciprofloxacin-resistant Escherichia coli WT-3-1 MB2 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360633Inhibition of human K562 cell proliferation assessed as [3H]thymidine incorporation after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360642Growth inhibition of african green monkey Vero cells assessed as [3H]thymidine incorporation at 50 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID673914Inhibition of Clostridium botulinum Hall BoNT/A protease activity using Ac-SNKTRIDEANQRATKML-NH2 as substrate after 5 mins by RP-HPLC analysis2012ACS medicinal chemistry letters, May-10, Volume: 3, Issue:5
Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.
AID673916Inhibition of Clostridium botulinum Hall BoNT/A-mediated paralysis in CD1 mouse phrenic nerve hemidiaphragm assessed as time required to 50% loss of twitch tension at 2 uM measured upto 5 hrs (Rvb = 62 mins)2012ACS medicinal chemistry letters, May-10, Volume: 3, Issue:5
Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.
AID733845Antibacterial activity against Escherichia coli ATCC 25922 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360622Growth inhibition of human HeLa cells assessed as [3H]thymidine incorporation at 25 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360637Growth inhibition of human Raji cells assessed as [3H]thymidine incorporation at 12.5 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID673915Inhibition of Clostridium botulinum Hall BoNT/A-mediated paralysis in CD1 mouse phrenic nerve hemidiaphragm assessed as time required to 50% loss of twitch tension at 20 uM measured upto 5 hrs (Rvb = 62 mins)2012ACS medicinal chemistry letters, May-10, Volume: 3, Issue:5
Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.
AID360649Growth inhibition of human WISH cells assessed as [3H]thymidine incorporation at 50 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID733846Antibacterial activity against Bacillus subtilis subsp. subtilis str. 168 trpC2 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360625Growth inhibition of human HeLa cells assessed as [3H]thymidine incorporation at 3.125 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360647Inhibition of african green monkey Vero cell proliferation assessed as [3H]thymidine incorporation after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID733849Antibacterial activity against doxycycline-intermediate Streptococcus agalactiae 013761 assessed as growth inhibition by CLSI broth microdilution method2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360632Growth inhibition of human K562 cells assessed as [3H]thymidine incorporation at 3.125 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360618Inhibition of human Calu1 cell proliferation assessed as [3H]thymidine incorporation after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360640Inhibition of human Raji cell proliferation assessed as [3H]thymidine incorporation after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360639Growth inhibition of human Raji cells assessed as [3H]thymidine incorporation at 3.125 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID733835Induction of recA promoter in Bacillus subtilis YB3001 using 4-methylumbelliferyl beta D-galactopyranoside as substrate incubated for 3 hrs prior to substrate addition measured after 1 hr by beta galactosidase reporter gene assay relative to control2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID733834Induction of yorB promoter in Bacillus subtilis IS34 after 3 hrs at 0.01 to 100 ug/ml by luciferase reporter gene assay2013Journal of medicinal chemistry, Apr-25, Volume: 56, Issue:8
Atropisomeric dihydroanthracenones as inhibitors of multiresistant Staphylococcus aureus.
AID360630Growth inhibition of human K562 cells assessed as [3H]thymidine incorporation at 12.5 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
AID360614Growth inhibition of human Calu1 cells assessed as [3H]thymidine incorporation at 50 uM after 3 days by scintillation counting2001Journal of natural products, May, Volume: 64, Issue:5
Cytotoxic principles from Ventilago leiocarpa.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (31.03)18.7374
1990's3 (10.34)18.2507
2000's4 (13.79)29.6817
2010's9 (31.03)24.3611
2020's4 (13.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 124.78

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index124.78 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.98 (4.65)
Search Engine Demand Index225.96 (26.88)
Search Engine Supply Index2.01 (0.95)

This Compound (124.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other28 (96.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ciprofloxacin
Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.		2.0810aminoquinoline;
cyclopropanes;
fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone;
zwitterion		antibacterial drug;
antiinfective agent;
antimicrobial agent;
DNA synthesis inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
environmental contaminant;
topoisomerase IV inhibitor;
xenobiotic
danthron
danthron: structure. chrysazin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.		1.9810dihydroxyanthraquinoneapoptosis inducer;
plant metabolite
emodin
Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.		3.470trihydroxyanthraquinoneantineoplastic agent;
laxative;
plant metabolite;
tyrosine kinase inhibitor
hypericin
[no description available]		2.6120
kojic acid
[no description available]		2.25104-pyranones;
enol;
primary alcohol		Aspergillus metabolite;
EC 1.10.3.1 (catechol oxidase) inhibitor;
EC 1.10.3.2 (laccase) inhibitor;
EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 1.4.3.3 (D-amino-acid oxidase) inhibitor;
NF-kappaB inhibitor;
skin lightening agent
patulin
Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.		3.1810furopyran;
gamma-lactone;
lactol		antimicrobial agent;
Aspergillus metabolite;
carcinogenic agent;
mutagen;
mycotoxin;
Penicillium metabolite
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.0810mitomycinalkylating agent;
antineoplastic agent
9,10-anthraquinone
9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.		2.8540anthraquinone
dimethyl ether
dimethyl ether : An ether in which the oxygen atom is connected to two methyl groups.		6.9310ether
ethyl acetate
ethyl acetate : The acetate ester formed between acetic acid and ethanol.		2.1110acetate ester;
ethyl ester;
volatile organic compound		EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor;
metabolite;
polar aprotic solvent;
Saccharomyces cerevisiae metabolite
perylene
Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.		2.6120ortho- and peri-fused polycyclic arene;
perylenes
funiculosin (anthraquinone)
funiculosin (anthraquinone): see also a pyridone cpd called funiculosin; structure		2.420trihydroxyanthraquinone
aloe emodin
aloe emodin: structure distinct from emodin; this does not mean emodin from aloe. Aloe emodin : A dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.		2.2510aromatic primary alcohol;
dihydroxyanthraquinone		antineoplastic agent;
plant metabolite
chrysophanic acid
chrysophanic acid: RN given refers to parent cpd; structure in Merck, 9th ed, #2260. chrysophanol : A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.		210dihydroxyanthraquinoneanti-inflammatory agent;
antiviral agent;
plant metabolite
physcione
physcione: structure. physcion : A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6. It has been widely isolated and characterised from both terrestrial and marine sources.		1.9810dihydroxyanthraquinoneanti-inflammatory agent;
antibacterial agent;
antifungal agent;
antineoplastic agent;
apoptosis inducer;
hepatoprotective agent;
metabolite
caproamide
[no description available]		2.2510primary carboxamide;
primary fatty amide
benomyl
[no description available]		1.9810aromatic amide;
benzimidazole fungicide;
benzimidazoles;
benzimidazolylcarbamate fungicide;
carbamate ester		acaricide;
anthelminthic drug;
antifungal agrochemical;
microtubule-destabilising agent;
tubulin modulator
luteoskyrin
luteoskyrin: mycotoxin from Penicillium islandicum; pollutant of stored rice; minor descriptor (75-85); on-line & Index Medicus search NAPHTHOQUINONES (75-85); RN given refers to (1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-isomer		1.9910
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.1110benzenes;
phenyl acetates
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.0710D-glucopyranoseepitope;
mouse metabolite
viridicatin
viridicatin: structure. viridicatin : A hydroxyquinolone that is 3-hydroxyuinolin-2(1H)-one which is substituted at position 4 by a phenyl groups. Isolated from the mycelium of several Penicillium species, it exhibits strong antibiotic activity against M. tuberculosis and also against B. subtilis, S. aureus and S. cerevisiae.		2.2510hydroxyquinolineantibacterial agent;
Aspergillus metabolite;
marine metabolite;
Penicillium metabolite
pinocembrin
pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.		2.2510(2S)-flavan-4-one;
dihydroxyflavanone		antineoplastic agent;
antioxidant;
metabolite;
neuroprotective agent;
vasodilator agent
avarol
avarol: RN given refers to parent cpd; extract from Dysidea avara(sea sponge)		2.2510
avarone
avarone: antileukemic agent; isolated from Dysidea avara		2.2510
altersolanol a
altersolanol A: isolated from fermentation product of fungus Alternaria porri(Ellis) Ciferri;RN given refers to (1R-(1alpha,2beta,3beta,4alpha))-isomer; structure given in first source		2.2510pentahydroxyanthraquinone
taraxerol
taraxerol: structure. taraxerol : A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.		210pentacyclic triterpenoid;
secondary alcohol		metabolite
xanthorrhizol
xanthorrhizol: structure in first source		2.2510sesquiterpenoid
aeroplysinin i
aeroplysinin I: isolated from sponge Aplysina sp.; RN refers to (1S-trans)-isomer; structure given in second source		2.2510tertiary alcohol
matairesinol
matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).		2.2510gamma-lactone;
lignan;
polyphenol		angiogenesis inhibitor;
anti-asthmatic agent;
phytoestrogen;
plant metabolite
aromadedrin
aromadedrin: inhibits protein kinase C; the dihydro makes it a flavone rather than a flavonol. (+)-dihydrokaempferol : A tetrahydroxyflavanone having hydroxy groupa at the 3-, 4'-, 5- and 7-positions.		2104'-hydroxyflavanones;
dihydroflavonols;
secondary alpha-hydroxy ketone;
tetrahydroxyflavanone		metabolite
macrosporin
macrosporin: isolated from fermentation product of fungus Alternaria porri (Ellis) Ciferri; structure given in first source		2.2510
sch 45752
[no description available]		2.0710organic heterotricyclic compound;
organooxygen compound
questin
[no description available]		1.9810dihydroxyanthraquinone
lupeol
[no description available]		210pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite
glycogen
glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.		210
cb 7969312
[no description available]		2.0710organochlorine compound;
quinolines
beauvericin
[no description available]		2.2510cyclodepsipeptideantibiotic insecticide;
antifungal agent;
antineoplastic agent;
apoptosis inhibitor;
fungal metabolite;
ionophore;
mycotoxin;
P450 inhibitor
asterric acid
asterric acid: structure given in first source; inhibits the binding of endothelin-1 to the ET(A) receptor of A10 cells		1.9810
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		2.6930
8-hydroxymanzamine a
8-hydroxymanzamine A: active against HIV-II; isolated from the sponge Pachypellina; structure in first source. 8-hydroxymanzamine A : An alkaloid that is manzamine A with a hydroxy substituent at position 8. Isolated from Pachypellina and Acanthostrongylophora, it exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).		2.2510alkaloid;
beta-carbolines;
isoquinolines		anti-HSV-2 agent;
EC 2.7.11.26 (tau-protein kinase) inhibitor;
metabolite
stigmasterol
stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.		2103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols;
stigmastane sterol		plant metabolite
neobavaisoflavone
neobavaisoflavone: isolated from Psoralea corylifolia; structure in first source. neobavaisoflavone : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone with an additonal hydroxy group at position 4' and a prenyl group at position 3'. Isolated from seeds of Psoralea corylifolia, it exhibits inhibitory activity against DNA polymerase and platelet aggregation.		2.25107-hydroxyisoflavonesantineoplastic agent;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
plant metabolite;
platelet aggregation inhibitor
alternariol monomethyl ether
djalonensone : A benzochromenone that is alternariol in which the hydroxy group at position 9 has been converted into the corresponding methyl ether. A natural product found in Chaetomium globosum as well as being one of the two most important compounds belonging to the group of Altenaria mycotoxins.		2.2510aromatic ether;
benzochromenone		antifungal agent;
fungal metabolite;
mycotoxin
luffariellolide
luffariellolide: structure given in first source; a partially reversible phospholipase A2 inhibitor; a major metabolite of the sponge Luffariella; do not confuse with luffolide, a minor metabolite of the same species		2.2510diterpene lactone
bakuchiol
bakuchiol: chief component of Psoralea corylifolia Linn; structure		2.2510
bavachalcone
bavachalcone: structure in first source		2.2510chalcones
rugulosin
rugulosin: RN given refers to cpd without isomeric designation; structure in first source & in Negwer, 5th ed, #5799		3.3470
aerothionin
[no description available]		2.2510isoxazolesmetabolite
glucagon
Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.		710peptide hormone
glucagon-like peptide 1
Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.		210
roquefortine
[no description available]		2.2510pyrroloindole
hygromycin b
[no description available]		1.9810
flavoskyrin
flavoskyrin: isolated from Penicillium islandicum Sopp.; structure given in first source		2.3620
cytoskyrin a
cytoskyrin A: structure in first source		7.0210
citrinin
Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.		3.1810
roseoside
roseoside: from Polygonum hydropiper L. (Polygonaceae); structure in first source		2.0710
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