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CHEBI:141600 - acaulide

ChEBI IDCHEBI:141600
ChEBI Nameacaulide
Stars
DefinitionA macrodiolide consisting of two (3E,5R,6S,9R,14S)-5-hydroxy-6,14-dimethyl-2,8,11-trioxo-1,7-dioxacyclotetradec-3-en-9-yl attached to position 1 of (6S)-6-methyldihydro-2H-pyran-2,4(3H)-dione. Isolated from a culture of Acaulium sp. H-JQSF associated with the isopod Armadillidium vulgare.
Last Modified17 August 2023
SubmitterCeri
DownloadsMolfile
FormulaC34H44O15
Net Charge0
Average Mass692.711
Monoisotopic Mass692.26802
SMILESC[C@@H]1OC(=O)[C@@H](C2([C@H]3CC(=O)CC[C@H](C)OC(=O)/C=C/[C@@H](O)[C@H](C)OC3=O)C(=O)C[C@H](C)OC2=O)CC(=O)CC[C@H](C)OC(=O)/C=C/[C@H]1O
InChIInChI=1S/C34H44O15/c1-17-6-8-22(35)15-24(31(42)48-20(4)26(37)10-12-29(40)45-17)34(28(39)14-19(3)47-33(34)44)25-16-23(36)9-7-18(2)46-30(41)13-11-27(38)21(5)49-32(25)43/h10-13,17-21,24-27,37-38H,6-9,14-16H2,1-5H3/b12-10+,13-11+/t17-,18-,19-,20-,21-,24-,25-,26+,27+/m0/s1
InChIKeyWPPOFQTZLGPDIZ-VPNZNENOSA-N
Species of MetaboliteComponentSourceComments
Acaulium sp. (ncbitaxon:1960041) - PubMed (29376657 ) Strain: H-JQSF
Roles Classification
Biological Role:
osteogenesis regulator  Any compound that induces or regulates osteogenesis.
Application:
bone density conservation agent  An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.
ChEBI Ontology
Outgoing Relation(s)
acaulide (CHEBI:141600) has role bone density conservation agent (CHEBI:50646)
acaulide (CHEBI:141600) has role osteogenesis regulator (CHEBI:63054)
acaulide (CHEBI:141600) is a cyclic ketone (CHEBI:3992)
acaulide (CHEBI:141600) is a macrodiolide (CHEBI:145556)
acaulide (CHEBI:141600) is a secondary alcohol (CHEBI:35681)
acaulide (CHEBI:141600) is a triketone (CHEBI:140322)
IUPAC Name 
(3E,5R,6S,9R,14S,3'E,5'R,6'S,9'R,14'S)-9,9'-[(6S)-6-methyl-2,4-dioxotetrahydro-2H-pyran-3,3-diyl]bis(5-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradec-3-ene-2,8,11-trione)
Citations