Compound: Genipin
SMILES: O=C(OC)C1=CO[C@@H](O)[C@H]2[C@@H]1CC=C2CO
InChIKey: AZKVWQKMDGGDSV-BCMRRPTOSA-N
Synonyms: Genipin, 6902-77-8, (+)-Genipin, methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate, A3V2NE52YG, DTXSID30894999, methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-4-carboxylate, RefChem:142877, DTXCID601324556, 636-196-5, 1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester, MFCD00888600, ST080860, CHEBI:5298, C09780, (1R,4aS,7aS)-methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate, methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate, AC1L9CSN, UNII-A3V2NE52YG, Genipin (Standard), SureCN34249, SCHEMBL34249, MLS006010198, CHEMBL459016, orb1306097, orb3140165, GLXC-06545, HMS3261H13, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R-(1.ALPHA.,4A.ALPHA.,7A.ALPHA.))-, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A.ALPHA.,5,7A.ALPHA.-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, EX-A4263, Tox21_500516, BDBM50565452, EBC-50094, Genipin, >=98% (HPLC), powder, HY-17389R, s2412, AKOS015851487, AC-8847, CCG-221820, FG30976, LP00516, SDCCGSBI-0633724.P001, NCGC00186010-01, NCGC00186010-03, NCGC00186010-10, NCGC00261201-01, AS-18947, HY-17389, SMR001456266, SY015025, G0458, NS00097440, AB01566854_01, EN300-7409283, F809725, Q1463401, BRD-K28824103-001-02-8, BRD-K28824103-001-04-4, Genipin is known as an aglycone dervied from Geniposide., Z2044761865, (1R,4aS,7aS)-1-Hydroxy-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester, 1202641-87-9, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R,4AS,7AS)-, Cyclopenta(c)pyran-4-carboxylic acid, 1,4a-alpha,5,7a-alpha-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester, Cyclopenta[c]pyran-4-carboxylic acid, 1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methylester, (1R,4aS,7aS)-, methyl (4aS,7aS,1R)-1-hydroxy-7-(hydroxymethyl)-1,5,4a,7a-tetrahydro-4aH-cyclo penta[1,2-d]pyran-4-carboxylate
Theoretical properties:
molecular_formula: C11H14O5
molecular_weight: 226.23 g/mol
exact_mass: 226.08412354 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 3
heavy_atom_count: 16
topological_polar_surface_area: 76 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Genipin is an iridoid monoterpenoid. It has a role as an uncoupling protein inhibitor, an antioxidant, a cross-linking reagent, a hepatotoxic agent, an anti-inflammatory agent and an apoptosis inhibitor.
chembl: GENIPIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Genipin is a chemical compound found in Genipa americana fruit extract.  It is an aglycone derived from an iridoid glycoside called geniposide which is also present in fruit of Gardenia jasminoides.
Genipin is an excellent natural cross-linker for proteins, collagen, gelatin, and chitosan cross-linking. It has a low acute toxicity, with LD50 i.v. 382 mg/kg in mice, therefore, much less toxic than glutaraldehyde and many other commonly used synthetic cross-linking reagents. Furthermore, genipin can be used as a regulating agent for drug delivery, as the raw material for gardenia blue pigment preparation, and as the intermediate for alkaloid syntheses.
In vitro experiments have shown that genipin blocks the action of the transporter uncoupling protein 2.