Structure Database (LMSD)

Common Name
Geniposidic acid
Systematic Name
Synonyms
LM ID
LMPR0102070043
Formula
Exact Mass
Calculate m/z
374.1213
Status
Curated


Classification

Biological Context

Geniposidic acid is an iridoid glycoside that has been found in G. jasminoides and has diverse biological activities.1,2,3 It inhibits ear edema induced by phorbol 12-myristate 13-acetate (TPA) in mice by 91.01% when administered topically at a dose of 0.1 mg/ear.1 Geniposidic acid (50 mg/kg) increases survival rate, attenuates increases in alanine aminotransferase (ALT) activity and TNF-α levels in serum, as well as hepatic levels of malondialdehyde (MDA), and prevents decreases in hepatic GSH levels in a mouse model of fulminant hepatic failure induced by D-galactosamine and LPS.2 It decreases systolic blood pressure and heart rate and increases plasma levels of atrial natriuretic peptide (ANP) in spontaneously hypertensive rats when administered at a dose of 100 mg/kg.3

This information has been provided by Cayman Chemical

References

3. Nakamura, K., Hosoo, S., Yamaguchi, S., et al. Geniposidic acid upregulates atrial natriuretic peptide secretion and lowers blood pressure in spontaneously hypertensive rat. J. Funct. Foods 40, 634-638 (2018).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Tarenna asiatica (#1378008)
Magnoliopsida (#3398)
Studies on monoterpene glucosides and related natural products. XXXII Iridoid Glucosides of Tarenna kotoensis var. gyokushinka,
Chem. Pharm. Bull, 1976

String Representations

InChiKey (Click to copy)
ZJDOESGVOWAULF-OGJQONSISA-N
InChi (Click to copy)
InChI=1S/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9-,10-,11-,12+,13-,15+,16+/m1/s1
SMILES (Click to copy)
[C@@]12([H])C(=CC[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)CO

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 3
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 328.26
Topological Polar Surface Area 170.28
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 10
logP -0.03
Molar Refractivity 86.26

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Created at
24th Jul 2020
Updated at
24th Jul 2020