CHEBI:31742 - kaempferol 3-O-β-D-galactoside

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ChEBI Name kaempferol 3-O-β-D-galactoside
ChEBI ID CHEBI:31742
ChEBI ASCII Name kaempferol 3-O-beta-D-galactoside
Definition A β-D-galactoside compound with a 4',5,7-trihydroxychromen-3-yl group at the anomeric position.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
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Retinal (also known as retinaldehyde) is a polyene chromophore. Retinal, bound to proteins called opsins, is the chemical basis of visual phototransduction, the light-detection stage of visual perception (vision). Some microorganisms use retinal to convert light into metabolic energy. One study suggests that approximately three billion years ago, most living organisms on Earth used retinal, rather than chlorophyll, to convert sunlight into energy. Because retinal absorbs mostly green light and transmits purple light, this gave rise to the Purple Earth hypothesis. Retinal itself is considered to be a form of vitamin A when eaten by an animal. There are many forms of vitamin A, all of which are converted to retinal, which cannot be made without them. The number of different molecules that can be converted to retinal varies from species to species. Retinal was originally called retinene, and was renamed after it was discovered to be vitamin A aldehyde. Vertebrate animals ingest retinal directly from meat, or they produce retinal from carotenoids – either from α-carotene or β-carotene – both of which are carotenes. They also produce it from β-cryptoxanthin, a type of xanthophyll. These carotenoids must be obtained from plants or other photosynthetic organisms. No other carotenoids can be converted by animals to retinal. Some carnivores cannot convert any carotenoids at all. The other main forms of vitamin A – retinol and a partially active form, retinoic acid – may both be produced from retinal. Invertebrates such as insects and squid use hydroxylated forms of retinal in their visual systems, which derive from conversion from other xanthophylls.
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Formula C21H20O11
Net Charge 0
Average Mass 448.37690
Monoisotopic Mass 448.10056
InChI InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17+,18-,21+/m1/s1
InChIKey JPUKWEQWGBDDQB-DTGCRPNFSA-N
SMILES OC[C@H]1O[C@@H](Oc2c(oc3cc(O)cc(O)c3c2=O)-c2ccc(O)cc2)[C@H](O)[C@@H](O)[C@H]1O
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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ChEBI Ontology
Outgoing kaempferol 3-O-β-D-galactoside (CHEBI:31742) has functional parent kaempferol (CHEBI:28499)
kaempferol 3-O-β-D-galactoside (CHEBI:31742) has role antifungal agent (CHEBI:35718)
kaempferol 3-O-β-D-galactoside (CHEBI:31742) has role plant metabolite (CHEBI:76924)
kaempferol 3-O-β-D-galactoside (CHEBI:31742) is a β-D-galactoside (CHEBI:28034)
kaempferol 3-O-β-D-galactoside (CHEBI:31742) is a glycosyloxyflavone (CHEBI:50018)
kaempferol 3-O-β-D-galactoside (CHEBI:31742) is a monosaccharide derivative (CHEBI:63367)
kaempferol 3-O-β-D-galactoside (CHEBI:31742) is a trihydroxyflavone (CHEBI:27116)
kaempferol 3-O-β-D-galactoside (CHEBI:31742) is conjugate acid of kaempferol 3-O-β-D-galactoside(1−) (CHEBI:76104)
Incoming kaempferol 3-O-β-D-galactoside(1−) (CHEBI:76104) is conjugate base of kaempferol 3-O-β-D-galactoside (CHEBI:31742)
IUPAC Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl β-D-galactopyranoside
Synonyms Sources
Kaempferol 3-O-beta-D-galactoside KEGG COMPOUND
Trifolin KEGG COMPOUND
Trifolioside HMDB
Manual Xrefs Databases
C00005137 KNApSAcK
C12626 KEGG COMPOUND
CPD-7260 MetaCyc
HMDB0030864 HMDB
LMPK12111663 LIPID MAPS
Trifolin Wikipedia
View more database links
Registry Numbers Types Sources
1359975 Reaxys Registry Number Reaxys
23627-87-4 CAS Registry Number ChemIDplus
Citations Types Sources
13534567 PubMed citation Europe PMC
15631505 PubMed citation Europe PMC
21923561 PubMed citation Europe PMC
22117193 PubMed citation Europe PMC
630002 PubMed citation Europe PMC
Last Modified
08 July 2015