CHEBI:9595 - tigogenin

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ChEBI Name tigogenin
ChEBI ID CHEBI:9595
Definition A widely used steroidal sapogenin isolated from several plant species and used for synthesizing steroid drugs.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H44O3
Net Charge 0
Average Mass 416.646
Monoisotopic Mass 416.32905
InChI InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
InChIKey GMBQZIIUCVWOCD-MFRNJXNGSA-N
SMILES [H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CO1)O2
Metabolite of Species Details
Agave lecheguilla (NCBI:txid39513) See: DOI
Yucca (NCBI:txid39550) See: PubMed
Digitalis lanata (NCBI:txid49450) See: DOI
Solanum scabrum (NCBI:txid795974) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): gout suppressant
A drug that increases uric acid excretion by the kidney (uricosuric drug), decreases uric acid production (antihyperuricemic), or alleviates the pain and inflammation of acute attacks of gout.
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ChEBI Ontology
Outgoing tigogenin (CHEBI:9595) has role gout suppressant (CHEBI:35845)
tigogenin (CHEBI:9595) has role plant metabolite (CHEBI:76924)
tigogenin (CHEBI:9595) is a sapogenin (CHEBI:26606)
Incoming tigogenin 3-O-β-D-glucopyranoside (CHEBI:166995) has functional parent tigogenin (CHEBI:9595)
IUPAC Name
(25R)-5α-spirostan-3β-ol
Synonyms Sources
(3-β,5α,25R)-spirostan-3-ol ChemIDplus
(5α,25R)-spirostan-3β-ol ChemIDplus
5-epi-sarsasapogenin FooDB
tigogenin UniProt
Manual Xrefs Databases
10252448 ChemSpider
C00003593 KNApSAcK
C08914 KEGG COMPOUND
FDB012684 FooDB
LMST01080009 LIPID MAPS
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Registry Numbers Types Sources
1293741 Reaxys Registry Number Reaxys
77-60-1 CAS Registry Number NIST Chemistry WebBook
77-60-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10923841 PubMed citation Europe PMC
11529418 PubMed citation Europe PMC
23707570 PubMed citation Europe PMC
28345921 PubMed citation Europe PMC
28677770 PubMed citation Europe PMC
29233733 PubMed citation Europe PMC
30693503 PubMed citation Europe PMC
30855957 PubMed citation Europe PMC
32439406 PubMed citation Europe PMC
32443910 PubMed citation Europe PMC
32751592 PubMed citation Europe PMC
33130020 PubMed citation Europe PMC
4036620 PubMed citation Europe PMC
IND605692811 Agricola citation Europe PMC
IND606860518 Agricola citation Europe PMC
Last Modified
07 December 2020