CHEBI:66402 - 8,8a-epoxymorellic acid

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ChEBI Name 8,8a-epoxymorellic acid
ChEBI ID CHEBI:66402
Definition An epoxide that is the 8,8a-epoxy derivative of morellic acid. Isolated from Garcinia hanburyi it exhibits cytotoxic and anti-HIV activity..
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5855401, ZINC000005854633
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Formula C33H36O9
Net Charge 0
Average Mass 576.63350
Monoisotopic Mass 576.23593
InChI InChI=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
InChIKey DHCUJGJZVIRMQU-ZZBIGSJJSA-N
SMILES [H][C@@]12C[C@@]3(C\C=C(\C)C(O)=O)C(C)(C)O[C@@]([H])(C1=O)[C@]31Oc3c(CC=C(C)C)c4OC(C)(C)C=Cc4c(O)c3C(=O)C11OC21
Metabolite of Species Details
Garcinia hanburyi (NCBI:txid231906) Found in latex (BTO:0000710). Previous component: resin; See: PubMed
Garcinia hanburyi (NCBI:txid231906) Found in fruit (BTO:0000486). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 α,β-unsaturated monocarboxylic acid (CHEBI:79020)
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)
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 Number Type Source
11109913 Reaxys Registry Number Reaxys
Citation Type Source
17117343 PubMed citation Europe PMC
Last Modified
27 June 2014