shinorine (CHEBI:131712)

CHEBI:131712 - shinorine

ChEBI ID	CHEBI:131712
ChEBI Name	shinorine
Stars
Definition	A mycosporine-like amino acid that is the ketimine resulting from the formal condensation of the amino group of L-serine with the keto group of (5S)-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-one and in which the hydrogen at position 3 of the cyclohexenone moiety has been replaced by the amino group of glycine. It is an active ingredient found in environmentally friendly sunscreen creams.
Last Modified	8 January 2020
Submitter	Kristian Axelsen
Downloads	Molfile

Formula	C13H20N2O8
Net Charge	0
Average Mass	332.309
Monoisotopic Mass	332.12197
SMILES	COC1=C(NCC(=O)O)C[C@@](O)(CO)C/C1=N\[C@@H](CO)C(=O)O
InChI	InChI=1S/C13H20N2O8/c1-23-11-7(14-4-10(18)19)2-13(22,6-17)3-8(11)15-9(5-16)12(20)21/h9,14,16-17,22H,2-6H2,1H3,(H,18,19)(H,20,21)/b15-8+/t9-,13-/m0/s1
InChIKey	WXEQFJUHQIGKNG-MZNRBSSJSA-N

Species of Metabolite	Component	Source	Comments
Palmaria palmata (ncbitaxon:2822)	-	Article (ISBN: 9789401773218)	See The Algae World, Dinabandhu Sahoo, Joseph Seckbach (Springer, 16 Dec 2015) p. 396
Pyropia columbina (ncbitaxon:688709)	-	Article (ISBN: 9789401773218)	See The Algae World, Dinabandhu Sahoo, Joseph Seckbach (Springer, 16 Dec 2015) p. 396
Chondrus crispus (ncbitaxon:2769)	-	Article (ISBN: 9789401773218)	See The Algae World, Dinabandhu Sahoo, Joseph Seckbach (Springer, 16 Dec 2015) p. 396
Curdiea racovitzia (ncbitaxon:172984)	-	Article (ISBN: 9789401773218)	See The Algae World, Dinabandhu Sahoo, Joseph Seckbach (Springer, 16 Dec 2015) p. 396

Roles Classification

antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

ultraviolet filter A photochemical role realized in the absorption of ultraviolet light, for example to protect skin cells from damage.

Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).

Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).

ChEBI Ontology

Outgoing Relation(s)
	shinorine (CHEBI:131712) has role antioxidant (CHEBI:22586)
	shinorine (CHEBI:131712) has role ultraviolet filter (CHEBI:73335)
	shinorine (CHEBI:131712) is a dicarboxylic acid (CHEBI:35692)
	shinorine (CHEBI:131712) is a ketimine (CHEBI:33272)
	shinorine (CHEBI:131712) is a mycosporine-like amino acid (CHEBI:35738)

IUPAC Name
(E)-N-[(5S)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]-L-serine

Registry Numbers	Sources
CAS:73112-73-9	ChemIDplus

Citations