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CHEBI:66401 - morellic acid

Default Structure
ChEBI IDCHEBI:66401
ChEBI Namemorellic acid
Stars
DefinitionA dioxo monocarboxylic acid derived from morellin by oxidation of the aldehyde group to the corresponding carboxy group. Isolated from Garcinia morella and Garcinia hanburyi, it exhibits antineoplastic, antibacterial and anti-HIV activity.
Last Modified11 April 2013
DownloadsMolfile
FormulaC33H36O8
Net Charge0
Average Mass560.643
Monoisotopic Mass560.24102
SMILES[H][C@@]12OC(C)(C)[C@]3(C/C=C(/C)C(=O)O)C[C@@]([H])(C=C4C(=O)c5c(O)c6c(c(CC=C(C)C)c5O[C@]431)OC(C)(C)C=C6)C2=O
InChIInChI=1S/C33H36O8/c1-16(2)8-9-20-26-19(11-12-30(4,5)39-26)24(35)22-25(36)21-14-18-15-32(13-10-17(3)29(37)38)31(6,7)41-28(23(18)34)33(21,32)40-27(20)22/h8,10-12,14,18,28,35H,9,13,15H2,1-7H3,(H,37,38)/b17-10-/t18-,28+,32+,33+/m1/s1
InChIKeyITPZQGLNWWAFMF-FXQQNLISSA-N
Species of MetaboliteComponentSourceComments
Garcinia hanburyi (ncbitaxon:231906)
latex (BTO:0000710) PubMed (17117343) Previous component: resin;
fruit (BTO:0000486) PubMed (17117343)
Garcinia morella (IPNI:428103-1) - DOI (10.1016/S0040-4039(00)90246-6)
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.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
morellic acid (CHEBI:66401) has functional parent morellin (CHEBI:6995)
morellic acid (CHEBI:66401) has role anti-HIV-1 agent (CHEBI:64947)
morellic acid (CHEBI:66401) has role antibacterial agent (CHEBI:33282)
morellic acid (CHEBI:66401) has role antineoplastic agent (CHEBI:35610)
morellic acid (CHEBI:66401) has role metabolite (CHEBI:25212)
morellic acid (CHEBI:66401) is a cyclic ether (CHEBI:37407)
morellic acid (CHEBI:66401) is a cyclic ketone (CHEBI:3992)
morellic acid (CHEBI:66401) is a dioxo monocarboxylic acid (CHEBI:35951)
morellic acid (CHEBI:66401) is a organic heterohexacyclic compound (CHEBI:51914)
morellic acid (CHEBI:66401) is a phenols (CHEBI:33853)
morellic acid (CHEBI:66401) is a polycyclic cage (CHEBI:33640)
Incoming Relation(s)
8,8a-epoxymorellic acid (CHEBI:66402) has functional parent morellic acid (CHEBI:66401)
IUPAC Name 
(2Z)-4-[(1R,3aS,5S,14aS)-8-hydroxy-3,3,11,11-tetramethyl-13-(3-methylbut-2-en-1-yl)-7,15-dioxo-5,7-dihydro-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-3a(4H)-yl]-2-methylbut-2-enoic acid
Citations