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CHEBI:138962 - 11-hydroxysugiol

Default Structure
ChEBI IDCHEBI:138962
ChEBI Name11-hydroxysugiol
Stars
DefinitionAn abietane diterpenoid that is sugiol in which the hydrogen ortho to the phenolic hydroxy group has been replaced by a hydroxy group.
Last Modified9 January 2018
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC20H28O3
Net Charge0
Average Mass316.441
Monoisotopic Mass316.20384
SMILES[H][C@@]12CC(=O)c3cc(C(C)C)c(O)c(O)c3[C@@]1(C)CCCC2(C)C
InChIInChI=1S/C20H28O3/c1-11(2)12-9-13-14(21)10-15-19(3,4)7-6-8-20(15,5)16(13)18(23)17(12)22/h9,11,15,22-23H,6-8,10H2,1-5H3/t15-,20-/m0/s1
InChIKeyGDLRDIDXYBIPFY-YWZLYKJASA-N
Species of MetaboliteComponentSourceComments
Caryopteris glutinosa (IPNI:861589-1) whole plant (BTO:0001461) PubMed (26900877) 95% EtOH extract
Caryopteris incana (ncbitaxon:41386) whole plant (BTO:0001461) DOI (10.1039/C6OB00139D)
Caryopteris mongholica (ncbitaxon:201515) aerial part (BTO:0001658) PubMed (25900047)
Plectranthus cyaneus (IPNI:454339-1) leaf (BTO:0000713) DOI (10.1002/hlca.200490210)
Salvia phlomoides (ncbitaxon:1520037) root (BTO:0001188) Article (Phytochemistry, 1983, 22(9), 2005-2009 1983)
Roles Classification
Biological Roles:
EC 3.1.1.7 (acetylcholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
EC 3.1.1.8 (cholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
11-hydroxysugiol (CHEBI:138962) has functional parent ferruginol (CHEBI:78274)
11-hydroxysugiol (CHEBI:138962) has functional parent sugiol (CHEBI:138961)
11-hydroxysugiol (CHEBI:138962) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
11-hydroxysugiol (CHEBI:138962) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
11-hydroxysugiol (CHEBI:138962) has role plant metabolite (CHEBI:76924)
11-hydroxysugiol (CHEBI:138962) is a abietane diterpenoid (CHEBI:36762)
11-hydroxysugiol (CHEBI:138962) is a carbotricyclic compound (CHEBI:38032)
11-hydroxysugiol (CHEBI:138962) is a catechols (CHEBI:33566)
11-hydroxysugiol (CHEBI:138962) is a cyclic terpene ketone (CHEBI:36130)
11-hydroxysugiol (CHEBI:138962) is a meroterpenoid (CHEBI:64419)
Incoming Relation(s)
11,20-dihydroxysugiol (CHEBI:138963) has functional parent 11-hydroxysugiol (CHEBI:138962)
IUPAC Name 
11,12-dihydroxyabieta-8,11,13-trien-7-one
Synonyms  Source
12-O-demethylcryptojapanolChEBI
12-O-demethylcryptojaponolChEBI
(4aS,10aS)-2,3,4,4a,10,10a-hexahydro-5,6-dihydroxy-1,1,4a-trimethyl-7-(1-methylethyl)phenanthren-9(1H)-oneChEBI
UniProt Name  Source
11-hydroxysugiolUniProt
Manual XrefsDatabases
CPD-20269MetaCyc
Registry NumbersSources
Reaxys:2060230Reaxys
Citations