Structure Database (LMSD)

Common Name
Loganic acid
Systematic Name
(1S,4aS,6S,7R,7aS)-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-cyclopenta[c]pyran-4-carboxylic acid
Synonyms
LM ID
LMPR01020138
Formula
C16H24O10
Exact Mass
Calculate m/z
376.13695
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C10 isoprenoids (monoterpenes) [PR0102]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Swertia (#39241)
Magnoliopsida (#3398)
Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis.,
Biochemistry, 1969
Pubmed ID: 5365793

String Representations

InChiKey (Click to copy)
JNNGEAWILNVFFD-CDJYTOATSA-N
InChi (Click to copy)
InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1
SMILES (Click to copy)
[C@@]12([H])[C@@H](C)[C@H](C[C@]1([H])C(C(=O)O)=CO[C@H]2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)O

Other Databases

Wikipedia
Loganic_acid
KEGG ID
C01512
CHEBI ID
30632
PubChem CID
89640
PDB ID
EQV

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 3
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 330.90
Topological Polar Surface Area 170.28
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 10
logP 0.05
Molar Refractivity 86.29

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Created at
26th Apr 2021
Updated at
26th Apr 2021