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CHEBI:83959 - hygrolidin

ChEBI IDCHEBI:83959
ChEBI Namehygrolidin
Stars
DefinitionA macrolide consisting resulting from the formal lactonisation of the carboxy group of (2E,4E,6R,7S,8S,10E,12E,14S,15R,16S,17R,18S)-18-[(2R,4R,5S,6R)-4-{[(2E)-3-carboxyprop-2-enoyl]oxy}-2-hydroxy-5,6-dimethyltetrahydro-2H-pyran-2-yl]-7,15,17-trihydroxy-14-methoxy-2,4,6,8,10,16-hexamethylnonadeca-2,4,10,12-tetraenoic acid with the hydroxy group at position 15. It is active against SV40 tumour cells, and inhibits the growth of solid tumour-derived cell lines such as DLD-1 human colon cancer cells with increased cells in G1 and S phases.
Last Modified26 November 2019
SubmitterSteve
DownloadsMolfile
FormulaC37H56O11
Net Charge0
Average Mass676.844
Monoisotopic Mass676.38226
SMILESCO[C@H]1/C=C/C=C(\C)C[C@H](C)[C@H](O)[C@H](C)/C=C(C)/C=C(\C)C(=O)O[C@@H]1[C@@H](C)[C@@H](O)[C@H](C)[C@@]1(O)C[C@@H](OC(=O)/C=C/C(=O)O)[C@@H](C)[C@@H](C)O1
InChIInChI=1S/C37H56O11/c1-20-12-11-13-29(45-10)35(47-36(43)24(5)18-21(2)17-23(4)33(41)22(3)16-20)26(7)34(42)27(8)37(44)19-30(25(6)28(9)48-37)46-32(40)15-14-31(38)39/h11-15,17-18,22-23,25-30,33-35,41-42,44H,16,19H2,1-10H3,(H,38,39)/b13-11+,15-14+,20-12+,21-17+,24-18+/t22-,23+,25-,26-,27-,28+,29-,30+,33-,34+,35+,37+/m0/s1
InChIKeyGEZBIZMDLMTFDB-KJKHOEIASA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
hygrolidin (CHEBI:83959) has role antimicrobial agent (CHEBI:33281)
hygrolidin (CHEBI:83959) has role antineoplastic agent (CHEBI:35610)
hygrolidin (CHEBI:83959) has role bacterial metabolite (CHEBI:76969)
hygrolidin (CHEBI:83959) is a cyclic hemiketal (CHEBI:59780)
hygrolidin (CHEBI:83959) is a enoate ester (CHEBI:51702)
hygrolidin (CHEBI:83959) is a ether (CHEBI:25698)
hygrolidin (CHEBI:83959) is a macrolide (CHEBI:25106)
hygrolidin (CHEBI:83959) is a oxanes (CHEBI:46942)
hygrolidin (CHEBI:83959) is a secondary alcohol (CHEBI:35681)
hygrolidin (CHEBI:83959) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(5R)-3-O-[(2E)-3-carboxyprop-2-enoyl]-2,4-dideoxy-1-C-{(2S,3R,4S)-3-hydroxy-4-[(2R,3S,4R,6R,9S,10S,11R,12R,14R)-10-hydroxy-3-methoxy-7,9,11,13,15-pentamethyl-16-oxooxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-4,5-dimethyl-β-L-erythro-pentopyranose
Registry NumbersSources
Reaxys:4629518Reaxys
Citations