11-hydroxysugiol (CHEBI:138962)

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ChEBI Name	11-hydroxysugiol

ChEBI ID	CHEBI:138962

Definition	An abietane diterpenoid that is sugiol in which the hydrogen ortho to the phenolic hydroxy group has been replaced by a hydroxy group.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Kristian Axelsen

Supplier Information

Download	Molfile XML SDF

Formula

C20H28O3

Net Charge

Average Mass

316.435

Monoisotopic Mass

316.20384

InChI

InChI=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

InChIKey

GDLRDIDXYBIPFY-YWZLYKJASA-N

SMILES

C1=C(C(C)C)C(=C(C2=C1C(C[C@@]3([C@@]2(CCCC3(C)C)C)[H])=O)O)O

Metabolite of Species	Details
Plectranthus cyaneus (IPNI:454339-1)	Found in leaf (BTO:0000713). See: DOI
Caryopteris glutinosa (IPNI:861589-1)	Found in whole plant (BTO:0001461). 95% EtOH extract See: PubMed
Salvia phlomoides (NCBI:txid1520037)	Found in root (BTO:0001188). See: Phytochemistry, 1983, 22(9), 2005-2009 1983
Caryopteris mongholica (NCBI:txid201515)	Found in aerial part (BTO:0001658). See: PubMed
Caryopteris incana (NCBI:txid41386)	Found in whole plant (BTO:0001461). See: DOI

Roles Classification
Biological Role(s):	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. (via meroterpenoid )

ChEBI Ontology
Outgoing	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	11,20-dihydroxysugiol (CHEBI:138963) has functional parent 11-hydroxysugiol (CHEBI:138962)

IUPAC Name

11,12-dihydroxyabieta-8,11,13-trien-7-one

Synonyms	Sources
(4aS,10aS)-2,3,4,4a,10,10a-hexahydro-5,6-dihydroxy-1,1,4a-trimethyl-7-(1-methylethyl)phenanthren-9(1H)-one	ChEBI
11-hydroxysugiol	UniProt
12-O-demethylcryptojapanol	ChEBI
12-O-demethylcryptojaponol	ChEBI

Registry Number	Type	Source
2060230	Reaxys Registry Number	Reaxys

Last Modified

09 January 2018