Structure Database (LMSD)

HO O HO O N H O
Common Name
N-jasmonoyl-L-tyrosine
Systematic Name
N-({(1R,2R)-3-Oxo-2-[(2Z)-Pent-2-En-1-Yl]cyclopentyl}acetyl)-L-tyrosine
Synonyms
LM ID
LMFA02020210
Formula
C21H27NO5
Exact Mass
Calculate m/z
373.188924
Sum Composition
NATyr 12:3;O
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
Jasmonic acids [FA0202]
Fatty amides [FA08]
N-acyl amines [FA0802]

String Representations

InChiKey (Click to copy)
SLWSWKGGZQCLDU-WHHQMRSUSA-N
InChi (Click to copy)
InChI=1S/C21H27NO5/c1-2-3-4-5-17-15(8-11-19(17)24)13-20(25)22-18(21(26)27)12-14-6-9-16(23)10-7-14/h3-4,6-7,9-10,15,17-18,23H,2,5,8,11-13H2,1H3,(H,22,25)(H,26,27)/b4-3-/t15-,17-,18+/m1/s1
SMILES (Click to copy)
C1(=O)[C@H](C/C=C\CC)[C@@H](CC(=O)N[C@H](C(=O)O)CC2=CC=C(O)C=C2)CC1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Vicia faba (#3906)
Magnoliopsida (#3398)
New metabolites of Gibberella fujikuroi. XV. N-jasmonoyl- and N-dihydrojasmonoyl-isoleucine.,
J Chem Soc Perkin 1, 1970
Pubmed ID: 5465381

Other Databases

PubChem CID
101772568

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 2
Aromatic Rings 1
Rotatable Bonds 9
Van der Waals Molecular Volume 372.71
Topological Polar Surface Area 103.70
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 3.13
Molar Refractivity 101.78

Admin

Created at
25th Feb 2021
Updated at
14th Feb 2024