e
ergosterol
Chemical compound
Also known as (22E,24S)-24-methylcholesta-5,7,22-trien-3beta-ol · Ergosta-5,7,22-trien-3beta-ol · 24alpha-Methyl-22E-dehydrocholesterol · Ergosterin · Ergosta-5,7,22-trien-3-ol, (3beta,22E)- · 24R-Methylcholesta-5,7,2E-trien-3beta-ol
- Formula
- C₂₈H₄₄O
1
- C₂₈H₄₄O
- Mass
- 396.339 Da
1
- 396.339 Da
Overview
Chemistry
All data
282 statements · 84% with external sources · numbers in brackets are citations
- Isomeric SMILES
- C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
1
- C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- Canonical SMILES
- CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C
1
- CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C
- Medical condition treated
- hypoparathyroidism(since 2009) approved by: United States Food and Drug Administration
1
Sources- 1.Stated in Inxight: Drugs Databasedrugs.ncats.io/drug/Z30RAY509FRetrieved 2018-11-02
- familial hypophosphatemia(since 2009) approved by: United States Food and Drug Administration
1
Sources- 1.Stated in Inxight: Drugs Databasedrugs.ncats.io/drug/Z30RAY509FRetrieved 2018-11-02
- hypoparathyroidism(since 2009) approved by: United States Food and Drug Administration
- Part of
- ergosterol biosynthetic process subject has role: product
1
- ergosterol metabolic process subject has role: participant
1
- cellular response to ergosterol subject has role: reactant
1
- delta24(24-1) sterol reductase activity
1
- 5-alpha-hydroxysteroid dehydratase activity
1
- ergosterol UDP-glucosyltransferase activity
1
- ergosterol biosynthetic process subject has role: product
- Found in taxon
- Lasiodiplodia theobromae
- Artemisia deserti
- Festuca arundinacea
- Epichloe coenophiala
- Spongionella gracilis
- Brachystegia nigerica
- Zoophagus insidians
- Agelas
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- Senna racemosa
- Cyanidium caldarium
- Galdieria sulphuraria
- Eutypa lata
- Ganoderma lucidum
6
Sources- 1.Stated in The major sterols from three species of polyporaceae
- 2.Stated in Steroids and triterpenes from the fruit bodies of Ganoderma lucidum and their anti-complement activity.
- 3.Stated in Lanostanoid triterpenes from Ganoderma applanatum
- 4.Stated in Anti-HIV-1 and anti-HIV-1-protease substances from Ganoderma lucidum
- 5.Stated in The biologically active constituents of Ganoderma lucidum (Fr.) Karst. Histamine release-inhibitory triterpenes
- 6.Stated in Lanostanoid Triterpenes fromGanodermalucidum
- Terfezia
- Pyrenophora graminea
- Pyrenophora teres
- Bombyx mori
- Cortinarius speciosissimus
- Ramaria botrytis
1
- Ramaria fennica
1
- Ramaria flavescens
1
- Ramaria formosa
1
- Clavicorona mairei
1
- Vitis vinifera
1
- Tuber melanosporum
- Dysidea avara
- Nervilia aragoana
- Heliopsis helianthoides var. scabra
1
- Aspergillus niger
- Ophiocordyceps sinensis
- Galactites tomentosus
1
- Aspergillus nidulans
3
Sources- 1.Stated in Structure of a novel epidithiodioxopiperazine, emethallicin A, a potent inhibitor of histamine release from Emericella heterothallica
- 2.Stated in Isolation of beta-amyrin from the fungus Aspergillus nidulans
- 3.Stated in Novel Epidithiodioxopiperazines, Emethallicins E and F, from Emericella heterothallica
- Dichotomophthora lutea
- Hebeloma vinosophyllum
- Apiosphaeria nipponica
1
- Cantharellus cibarius
- Aspergillus rugulosus
- Alternaria raphani
- Polyporus tuberaster
- Cryptoporus volvatus
- Mikania rimachii
- Diaporthe convolvuli
- Sirococcus
- Lactarius volemus
- Lactifluus volemus
- Cuphea carthagenensis
- Aspergillus alliaceus
- Ramalina
- Tornabea scutellifera
- Cephalosporium aphidicola
1
- Lactarius deliciosus
- Pleurotus ostreatus
- Clitocybula oculus
- Aspergillus purpureus
- Colletotrichum
- Panellus serotinus
- Hohenbuehelia serotina
- Chaetomium globosum
- Inonotus obliquus
- Paxillus involutus
- Stereoisomer of
- (3S,9S,10S,13R,14S,17R)-17-[(E,2S,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3S,9S,10R,13R,14R,17S)-17-[(E,2R,5S)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- lumisterol
- (3S,9S,10R,13R,14S,17R)-17-[(E,2S,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3S,9R,10R,13S,14S,17R)-17-[(Z,2S,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3S,9S,10R,13R,14R,17R)-17-[(Z,2S,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3S,9R,10R,13R,14S,17R)-17-[(E,2S,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3S,9R,10S,13R,14S,17R)-17-[(E,2S,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
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- ergosta-5,8,20(22)-trien-3-ol
- (3S,9R,10R,13R,14S,17R)-17-[(Z,2S,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- Epiergosterol
- pyrocalciferol
- isopyrocalciferol
- (3beta,22E)-ergosta-5,7,22-trien-3-ol
- (3S,9S,10R,13R,14R,17R)-17-[(Z,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- (3S,9R,10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
On other databases
45 identifiers linking ergosterol across the web's reference databases
- Cannabis Database ID006155
- CAS Registry Number57-87-4
- ChEBI ID16933
- ChEMBL IDCHEMBL1232562
- ChemSpider ID392539
- CosIng number33778
- DeCS ID4958
- DrugBank IDDB04038
- DSSTOX compound identifierDTXCID201016721
- DSSTox substance IDDTXSID90878679
- EC number200-352-7
- ECHA Substance Infocard ID100.000.320
- Encyclopædia Britannica Online IDscience/ergosterol
- FAST ID914659
- Freebase ID/m/03g7x_
- GND ID4306749-9
- Gran Enciclopèdia Catalana IDergosterol
- Gran Enciclopèdia Catalana ID (former scheme)0103881
- HSDB ID395
- Human Metabolome Database IDHMDB0000878
- InChIInChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
- InChIKeyDNVPQKQSNYMLRS-APGDWVJJSA-N
- KEGG IDC01694
- KNApSAcK IDC00023755
- Lex IDergosterol
- LIPID MAPS IDLMST01030093
- MeSH descriptor IDD004875
- MeSH tree codeD04.210.500.247.222.537
- Microsoft Academic ID (discontinued)2777910421
- NL CR AUT IDph280226
- OpenAlex IDC2777910421
- PDB ligand IDERG
- PDB structure ID1ZHZ
- Probes And Drugs IDPD041159
- PubChem CID444679
- Reaxys registry number2338604
- Store medisinske leksikon IDergosterol
- SureChEMBL ID43194
- SwissLipids IDSLM:000000326
- Treccani IDergosterolo
- UniChem compound ID655574
- UNIIZ30RAY509F
- Wellcome Collection concept IDqgmanexv
- WordNet 3.1 Synset ID15083971-n
- YSO ID38976