CHEBI:132927 - (+)-pentacycloanammoxic acid

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ChEBI Name (+)-pentacycloanammoxic acid
ChEBI ID CHEBI:132927
Definition A carbocyclic fatty acid consisting of octanoic acid which is terminally substituted by five fused cyclobutane-rings ([5]-ladderane). Ladderane fatty acids can be found in anammox bacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter mbuss
Supplier Information
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Formula C20H30O2
Net Charge 0
Average Mass 302.452
Monoisotopic Mass 302.22458
InChI InChI=1S/C20H30O2/c21-15(22)7-5-3-1-2-4-6-11-10-14-16(11)20-18-13-9-8-12(13)17(18)19(14)20/h11-14,16-20H,1-10H2,(H,21,22)/t11-,12-,13+,14-,16+,17+,18-,19-,20+/m0/s1
InChIKey ZKKJRZDMLYQUNK-QIPWGTBCSA-N
SMILES [C@@]12([C@]3([C@@]([C@]1([C@@]4(CC[C@]24[H])[H])[H])([C@]5([C@@]3(C[C@@H]5CCCCCCCC(O)=O)[H])[H])[H])[H])[H]
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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ChEBI Ontology
Outgoing (+)-pentacycloanammoxic acid (CHEBI:132927) has functional parent octanoic acid (CHEBI:28837)
(+)-pentacycloanammoxic acid (CHEBI:132927) is a carbocyclic fatty acid (CHEBI:35744)
(+)-pentacycloanammoxic acid (CHEBI:132927) is a ladderane (CHEBI:85034)
(+)-pentacycloanammoxic acid (CHEBI:132927) is a saturated fatty acid (CHEBI:26607)
Incoming methyl (+)-pentacycloanammoxate (CHEBI:132928) has functional parent (+)-pentacycloanammoxic acid (CHEBI:132927)
IUPAC Name
8-[(1S,2R,3R,4S,6S,7S,8S,9S,12R)-pentacyclo[6.4.0.02,7.03,6.09,12]dodecan-4-yl]octanoic acid
Synonym Source
8-[5]-ladderane-octanoic acid LIPID MAPS
Manual Xrefs Databases
8147776 ChemSpider
9972184 PubChem
LMFA01140004 LIPID MAPS
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Citation Waiting for Citations Type Source
16522072 PubMed citation Europe PMC
Last Modified
28 February 2018
General Comment
2018-02-28 For enantioselective synthesis, see Enantioselective Chemical Synthesis: Methods, Logic, and Practice by Elias J. Corey, Laszlo Kurti (Elsevier, 2013).