CHEBI:141600 - acaulide

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ChEBI Name acaulide
ChEBI ID CHEBI:141600
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Ceri
Supplier Information
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Formula C34H44O15
Net Charge 0
Average Mass 692.711
Monoisotopic Mass 692.26802
InChI InChI=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
InChIKey WPPOFQTZLGPDIZ-VPNZNENOSA-N
SMILES [C@@H]1(CCC(C[C@@H](C(O[C@H]([C@@H](C=CC(O1)=O)O)C)=O)C2([C@H]3CC(CC[C@@H](OC(C=C[C@H]([C@@H](OC3=O)C)O)=O)C)=O)C(O[C@H](CC2=O)C)=O)=O)C
Metabolite of Species Details
Acaulium sp. (NCBI:txid1960041) of strain H-JQSF See: PubMed
Roles Classification
Biological Role(s): osteogenesis regulator
Any compound that induces or regulates osteogenesis.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Waiting for Citations Types Sources
29376657 PubMed citation SUBMITTER
32619097 PubMed citation Europe PMC
34980745 PubMed citation Europe PMC
Last Modified
17 August 2023