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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H14O5
Molecular Weight 226.2259
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENIPIN

SMILES

[H][C@]12CC=C(CO)[C@@]1([H])[C@H](O)OC=C2C(=O)OC

InChI

InChIKey=AZKVWQKMDGGDSV-BCMRRPTOSA-N
InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1

HIDE SMILES / InChI

Molecular Formula C11H14O5
Molecular Weight 226.2259
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Genipin is an aglycone derived from an iridoid glycoside called Geniposide (structure on the bottom) present in fruit of Gardenia jasmindides Ellis. Genipin have been demonstrated to have diverse pharmacological activities including anti-inflammatory, antioxidative, neuroprotective, and neurotrophic effects. Genipin is an excellent natural cross-linker for protein, collagen, gelatin, and chitosan cross-linking and can be considered as a substitute for glutaraldehyde. Due to cross-linking properties genipin can be used in controlling drug delivery. In addition genipin exerts choleretic action.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Oral genipin, at dose 50 mg/kg, exerts anti-inflammatory activity in carrageenan-induced rat paw edema
Route of Administration: Oral
In Vitro Use Guide
Genipin reduced the viability of K562 cells with an IC(50) value of approximately 250 μmol/L. Genipin 200-400 μmol/L induced formation of typical apoptotic bodies and DNA fragmentation.
Substance Class Chemical
Record UNII
A3V2NE52YG
Record Status Validated (UNII)
Record Version