Compounds > illudin s
Page last updated: 2024-12-07

illudin s

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

Cross-References

ID SourceID
PubMed CID344200
CHEMBL ID509170
CHEBI ID5867
SCHEMBL ID1743370
MeSH IDM0051674

Synonyms (43)

Synonym
2',3'-dihydro-2',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one
nsc 626369
ccris 3540
sprio(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one, 2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-, (2's,3'r,6'r)-
brn 2336420
nsc 400979
illudine s
spiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one, 2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-, (2's-(2'alpha,3'beta,6'alpha))-
lunamycin
NCI60_003751
NSC400979 ,
dr-15978
spiro[cyclopropane-1, 2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-, [2's-(2'.alpha.,3'.beta.,6'.alpha.)]-
lampterol
spiro[cyclopropane-1, 2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-
nsc-400979
C09688
1149-99-1
illudin s ,
LMPR0103590002
(-)-illudin s
(-)-1alpha,7beta,12-trihydroxy-2,9-illudadien-8-one
chebi:5867 ,
CHEMBL509170
(1r,2s,5r)-1,5-dihydroxy-2-(hydroxymethyl)-2,5,7-trimethylspiro[1h-indene-6,1'-cyclopropane]-4-one
unii-ewj0gy2h7x
ewj0gy2h7x ,
(2's-(2'.alpha.,3'.beta.,6'.alpha.))-2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one
lunamycin (obsolete)
spiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one, 2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-, (2's,3'r,6'r)-
illudin s [mi]
SCHEMBL1743370
DDLLIYKVDWPHJI-RDBSUJKOSA-N
J-003167
HY-125098
CS-0089316
Q27106920
EX-A5056
AC-36761
(2's,3'r,6'r)-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-inden]-7'-one
(2's,3'r,6'r)-2',3'-dihydro-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-[5h]inden]-7'(6'h)-one
DTXSID601031301
AKOS040745210

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" While illudins are toxic to most tumor cells after prolonged exposure (greater than or equal to 48 hr), with shorter exposure times (less than or equal to 2 hr), they show selective toxicity for human myelocytic leukemia and epidermoid, lung, ovarian, and breast carcinoma cells of various species of origin."( Preclinical evaluation of illudins as anticancer agents: basis for selective cytotoxicity.
Kelner, MJ; McMorris, TC; Taetle, R, 1990)		0.28
" In vitro killing of tumor cells by acylfulvene required up to a 30-fold increase in molecules per cell, as compared with illudin S, indicating that acylfulvene was less toxic on a cellular level."( Characterization of acylfulvene histiospecific toxicity in human tumor cell lines.
Bagnell, RD; Estes, L; Kelner, MJ; McMorris, TC; Montoya, MA; Rutherford, M; Samson, KM; Taetle, R; Uglik, SF, 1998)		0.3

Dosage Studied

ExcerptRelevanceReference
" Rats were dosed orally with illudin S, a toxic substance derived from the poisonous mushroom Lampteromyces japonicus."( Histopathological effects of illudin S, a toxic substance of poisonous mushroom, in rat.
Inoue, T; Miyasaka, S; Tanaka, K, 1996)		0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
sesquiterpenoidAny terpenoid derived from a sesquiterpene. The term includes compounds in which the C15 skeleton of the parent sesquiterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[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]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID398543Cytotoxicity against human HL60 cells after 48 hrs by trypan blue exclusion assay2003Journal of natural products, Feb, Volume: 66, Issue:2
Reaction of irofulven with zinc and acid.
AID356458Antiviral activity against HSV1 infected in african green monkey CV1 cells at 0.5 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356456Antiviral activity against HSV1 infected in african green monkey CV1 cells at 1 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356460Antiviral activity against HSV1 infected in african green monkey CV1 cells at 0.25 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356468Cytotoxicity against african green monkey CV1 cells at 0.025 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356457Cytotoxicity against african green monkey CV1 cells at 1 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356467Cytotoxicity against african green monkey CV1 cells at 0.05 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356465Cytotoxicity against african green monkey CV1 cells at 0.1 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356459Cytotoxicity against african green monkey CV1 cells at 0.5 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356470Antiviral activity against HSV1 infected in african green monkey CV1 cells at 0.010 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356454Antiviral activity against HSV1 infected in african green monkey CV1 cells at 2.5 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356472Antiviral activity against HSV1 infected in african green monkey CV1 cells at 0.005 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356469Cytotoxicity against african green monkey CV1 cells at 0.015 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356453Cytotoxicity against african green monkey CV1 cells at 5 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356466Antiviral activity against HSV1 infected in african green monkey CV1 cells at 0.05 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356461Cytotoxicity against african green monkey CV1 cells at 0.25 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID402496In vivo antitumor activity against mouse P388 cells assessed as increase in life span at 5 mg/kg, ip for 5 days1997Journal of natural products, Feb, Volume: 60, Issue:2
Illudinic acid, a novel illudane sesquiterpene antibiotic.
AID356473Cytotoxicity against african green monkey CV1 cells at 0.005 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356450Antiviral activity against HSV1 infected in african green monkey CV1 cells at 10 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356463Cytotoxicity against african green monkey CV1 cells at 0.15 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356452Antiviral activity against HSV1 infected in african green monkey CV1 cells at 5 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356451Cytotoxicity against african green monkey CV1 cells at 10 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356455Cytotoxicity against african green monkey CV1 cells at 2.5 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356462Antiviral activity against HSV1 infected in african green monkey CV1 cells at 0.15 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356471Cytotoxicity against african green monkey CV1 cells at 0.010 ug/disk by neutral red staining2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
AID356464Antiviral activity against HSV1 infected in african green monkey CV1 cells at 0.1 ug/disk by filter disk method2003Journal of natural products, Sep, Volume: 66, Issue:9
Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (22.73)18.7374
1990's15 (34.09)18.2507
2000's8 (18.18)29.6817
2010's9 (20.45)24.3611
2020's2 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (4.35%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other44 (95.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carmustine
Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.		1.9810N-nitrosoureas;
organochlorine compound		alkylating agent;
antineoplastic agent
hydroxyurea
[no description available]		2.1310one-carbon compound;
ureas		antimetabolite;
antimitotic;
antineoplastic agent;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
genotoxin;
immunomodulator;
radical scavenger;
teratogenic agent
metoclopramide
Metoclopramide: A dopamine D2 antagonist that is used as an antiemetic.. metoclopramide : A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.		3.1810benzamides;
monochlorobenzenes;
substituted aniline;
tertiary amino compound		antiemetic;
dopaminergic antagonist;
environmental contaminant;
gastrointestinal drug;
xenobiotic
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		1.9910acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
vancomycin
Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.		1.9910glycopeptideantibacterial drug;
antimicrobial agent;
bacterial metabolite
glutathione disulfide
Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.		2.0510glutathione derivative;
organic disulfide		Escherichia coli metabolite;
mouse metabolite
ecteinascidin 743
[no description available]		2.0110acetate ester;
azaspiro compound;
bridged compound;
hemiaminal;
isoquinoline alkaloid;
lactone;
organic heteropolycyclic compound;
organic sulfide;
oxaspiro compound;
polyphenol;
tertiary amino compound		alkylating agent;
angiogenesis modulating agent;
anti-inflammatory agent;
antineoplastic agent;
marine metabolite
irofulven
irofulven: structure in first source		8.4170cyclohexenones
wortmannin
[no description available]		3.2110acetate ester;
cyclic ketone;
delta-lactone;
organic heteropentacyclic compound		anticoronaviral agent;
antineoplastic agent;
autophagy inhibitor;
EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor;
geroprotector;
Penicillium metabolite;
radiosensitizing agent
illudin m
[no description available]		3.2560sesquiterpenoid
acylfulvene
acylfulvene: an antineoplastic agent; structure given in first source; an analog of illudin		3.5380
nsc 141537
diacetoxyscirpenol: mycotoxin belonging to 12,13-epoxytrichothecene group; RN given refers to (3alpha,4beta)-isomer; structure		3.2110trichothecene
aphidicolin
Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.		3.2110tetracyclic diterpenoidantimicrobial agent;
antimitotic;
antineoplastic agent;
antiviral drug;
apoptosis inducer;
Aspergillus metabolite;
DNA synthesis inhibitor;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
fungal metabolite
sesquiterpenes
[no description available]		6.59390
nadp
[no description available]		2.7130
sodium borohydride
sodium borohydride: RN given refers to parent cpd		2.0610inorganic sodium salt;
metal tetrahydridoborate
quercetin
[no description available]		1.98107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
vitamin k semiquinone radical
vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.		1.9810
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		7.4220cysteiniumfundamental metabolite
selenocysteine
Selenocysteine: A naturally occurring amino acid in both eukaryotic and prokaryotic organisms. It is found in tRNAs and in the catalytic site of some enzymes. The genes for glutathione peroxidase and formate dehydrogenase contain the TGA codon, which codes for this amino acid.. selenocysteine : An alpha-amino acid that consists of alanine where one of the methyl hydrogens is substituted with a seleno group.		2.0610
rhizoxin
rhizoxin: from Rhizopus chinensis; causal agent of rice seedling blight; structure given in first source. rhizoxin : An macrolide antibiotic isolated from the pathogenic plant fungus Rhizopus microsporus. It also exhibits antitumour and antimitotic activity.		3.21101,3-oxazoles;
epoxide;
macrolide antibiotic		antimitotic;
antineoplastic agent;
metabolite
fumagillin
[no description available]		3.2110antibiotic antifungal drug;
carboxylic ester;
dicarboxylic acid monoester;
meroterpenoid;
organooxygen heterocyclic antibiotic;
spiro-epoxide		angiogenesis inhibitor;
antibacterial drug;
antimicrobial agent;
antiprotozoal drug;
fungal metabolite;
methionine aminopeptidase 2 inhibitor
phenylahistin
phenylahistin: antineoplastic from Aspergillus ustus; structure in first source		3.2110
ptaquiloside
ptaquiloside: a norsesquiterpene from bracken fern (Pteridium aquilinum); not a pteridine; can be activated to alkylate DNA		2.3820
dicumarol
Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.		1.9810hydroxycoumarinanticoagulant;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
Hsp90 inhibitor;
vitamin K antagonist
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		01.9910
Mushroom Poisoning
Poisoning from ingestion of mushrooms, primarily from, but not restricted to, toxic varieties.		03.8340
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		03.0310
Benign Neoplasms
[description not available]		03.9240
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.9240
Carcinoma, Anaplastic
[description not available]		02.0110
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		02.0110
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		01.9310
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0210
Cancer of Lung
[description not available]		02.3920
Lung Neoplasms
Tumors or cancer of the LUNG.		02.3920
Abnormalities, Autosome
[description not available]		01.9710
Leukemia, Lymphocytic
[description not available]		01.9710
Malignant Melanoma
[description not available]		01.9710
Acute Myelogenous Leukemia
[description not available]		01.9710
Leukemia, Lymphoid
Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.		01.9710
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		01.9710
Leukemia, Myeloid, Acute
Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.		01.9710