Structure Database (LMSD)
Common Name
Geniposidic acid
Systematic Name
Synonyms
3D model of Geniposidic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
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
Chem. Pharm. Bull, 1976
DOI:
10.1248/cpb.24.1216
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
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
Admin
Created at
24th Jul 2020
Updated at
24th Jul 2020