CHEBI:9375 - symphytine

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ChEBI Name symphytine
ChEBI ID CHEBI:9375
Definition A but-2-enoate ester obtained by formal condensation of the carboxy group of (2E)-2-methylbut-2-enoic acid with the 1-hydroxy group of (1R,7aR)-7-({[(2S,3S)-2,3-dihydroxy-2-isopropylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H31NO6
Net Charge 0
Average Mass 381.46320
Monoisotopic Mass 381.21514
InChI InChI=1S/C20H31NO6/c1-6-13(4)18(23)27-16-8-10-21-9-7-15(17(16)21)11-26-19(24)20(25,12(2)3)14(5)22/h6-7,12,14,16-17,22,25H,8-11H2,1-5H3/b13-6+/t14-,16+,17+,20-/m0/s1
InChIKey MVWPTZQHBOWRTF-SMLWLWDZSA-N
SMILES [H][C@@]12[C@@H](CCN1CC=C2COC(=O)[C@](O)(C(C)C)[C@H](C)O)OC(=O)C(\C)=C\C
ChEBI Ontology
Outgoing symphytine (CHEBI:9375) is a but-2-enoate ester (CHEBI:50654)
symphytine (CHEBI:9375) is a pyrrolizines (CHEBI:38522)
Incoming symphytine oxide (CHEBI:63917) has functional parent symphytine (CHEBI:9375)
IUPAC Name
(1R,7aR)-7-({[(2S,3S)-2,3-dihydroxy-2-isopropylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2E)-2-methylbut-2-enoate
Synonyms Sources
7-Tiglyl-9-(-)-viridiflorylretronecine KEGG COMPOUND
7-Tiglylretronecine viridiflorate ChemIDplus
Symphytine KEGG COMPOUND
Manual Xrefs Databases
C00002123 KNApSAcK
C10409 KEGG COMPOUND
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Registry Numbers Types Sources
1554309 Reaxys Registry Number Reaxys
22571-95-5 CAS Registry Number KEGG COMPOUND
22571-95-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11430014 PubMed citation Europe PMC
15482618 PubMed citation Europe PMC
17401847 PubMed citation Europe PMC
287835 PubMed citation Europe PMC
6579012 PubMed citation Europe PMC
7128756 PubMed citation Europe PMC
IND90038070 Agricola citation Europe PMC
Last Modified
28 July 2014