shinorine (CHEBI:131712)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	shinorine

ChEBI ID	CHEBI:131712

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and in which the hydrogen at position 3 of the cyclohexenone moiety has been replaced by the amino group of glycine.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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Kristian Axelsen

Supplier Information

Download	Molfile XML SDF

Formula

C13H20N2O8

Net Charge

Average Mass

332.309

Monoisotopic Mass

332.12197

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

SMILES

C/1(\C[C@@](CC(=C1OC)NCC(O)=O)(CO)O)=N\[C@@H](CO)C(O)=O

Metabolite of Species	Details
Curdiea racovitzia (NCBI:txid172984)	See The Algae World, Dinabandhu Sahoo, Joseph Seckbach (Springer, 16 Dec 2015) p. 396 See: ISBN: 9789401773218
Chondrus crispus (NCBI:txid2769)	See The Algae World, Dinabandhu Sahoo, Joseph Seckbach (Springer, 16 Dec 2015) p. 396 See: ISBN: 9789401773218
Palmaria palmata (NCBI:txid2822)	See The Algae World, Dinabandhu Sahoo, Joseph Seckbach (Springer, 16 Dec 2015) p. 396 See: ISBN: 9789401773218
Pyropia columbina (NCBI:txid688709)	See The Algae World, Dinabandhu Sahoo, Joseph Seckbach (Springer, 16 Dec 2015) p. 396 See: ISBN: 9789401773218

Roles Classification
Chemical Role(s):	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 base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

ChEBI Ontology
Outgoing	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 Number	Type	Source
73112-73-9	CAS Registry Number	ChemIDplus

Last Modified

08 January 2020