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CHEBI:66402 - 8,8a-epoxymorellic acid

ChEBI IDCHEBI:66402
ChEBI Name8,8a-epoxymorellic acid
Stars
DefinitionAn epoxide that is the 8,8a-epoxy derivative of morellic acid. Isolated from Garcinia hanburyi it exhibits cytotoxic and anti-HIV activity..
Last Modified27 June 2014
DownloadsMolfile
FormulaC33H36O9
Net Charge0
Average Mass576.642
Monoisotopic Mass576.23593
SMILES[H][C@]12OC(C)(C)[C@]3(C/C=C(/C)C(=O)O)C[C@]([H])(C1=O)C1OC14C(=O)c1c(O)c5c(c(CC=C(C)C)c1O[C@]432)OC(C)(C)C=C5
InChIInChI=1S/C33H36O9/c1-15(2)8-9-18-23-17(11-12-29(4,5)39-23)21(34)20-24(18)40-33-27-22(35)19(26-32(33,42-26)25(20)36)14-31(33,30(6,7)41-27)13-10-16(3)28(37)38/h8,10-12,19,26-27,34H,9,13-14H2,1-7H3,(H,37,38)/b16-10-/t19-,26?,27+,31+,32?,33+/m1/s1
InChIKeyDHCUJGJZVIRMQU-ZZBIGSJJSA-N
Species of MetaboliteComponentSourceComments
Garcinia hanburyi (ncbitaxon:231906)
fruit (BTO:0000486) PubMed (17117343)
latex (BTO:0000710) PubMed (17117343) Previous component: resin;
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
anti-HIV-1 agent  An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
8,8a-epoxymorellic acid (CHEBI:66402) has functional parent morellic acid (CHEBI:66401)
8,8a-epoxymorellic acid (CHEBI:66402) has role anti-HIV-1 agent (CHEBI:64947)
8,8a-epoxymorellic acid (CHEBI:66402) has role antineoplastic agent (CHEBI:35610)
8,8a-epoxymorellic acid (CHEBI:66402) has role metabolite (CHEBI:25212)
8,8a-epoxymorellic acid (CHEBI:66402) is a cyclic ketone (CHEBI:3992)
8,8a-epoxymorellic acid (CHEBI:66402) is a dioxo monocarboxylic acid (CHEBI:35951)
8,8a-epoxymorellic acid (CHEBI:66402) is a epoxide (CHEBI:32955)
8,8a-epoxymorellic acid (CHEBI:66402) is a organic heterohexacyclic compound (CHEBI:51914)
8,8a-epoxymorellic acid (CHEBI:66402) is a phenols (CHEBI:33853)
8,8a-epoxymorellic acid (CHEBI:66402) is a polycyclic cage (CHEBI:33640)
8,8a-epoxymorellic acid (CHEBI:66402) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(2Z)-4-[(2S,3aR,6S,6aR)-13-hydroxy-5,5,10,10-tetramethyl-8-(3-methylbut-2-en-1-yl)-3,14-dioxo-1a,2,3,3a-tetrahydro-10H,14H-2,6-methanofuro[3,2-g]oxireno[k]pyrano[3,2-b]xanthen-6(5H)-yl]-2-methylbut-2-enoic acid
Registry NumbersSources
Reaxys:11109913Reaxys
Citations