Compound: Loganic acid
SMILES: O=C(O)C1=CO[C@@H](O[C@@H]2O[C@@H]([C@@H](O)[C@@H]([C@H]2O)O)CO)[C@H]3[C@@H]1C[C@H](O)[C@@H]3C
InChIKey: JNNGEAWILNVFFD-CDJYTOATSA-N
Synonyms: Loganic acid, 22255-40-9, UX3J3KK2UG, (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid, CHEBI:30632, DTXSID80944913, (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid, (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylic acid, (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylic acid, RefChem:153948, DTXCID801373242, 244-875-9, Loganin acid, MFCD00017417, (1S,4aS,6S,7R,7aS)-6-Hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid, (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid, Loganic-acid, EINECS 244-875-9, Spectrum_001509, SpecPlus_000543, Loganic acid (Standard), Spectrum2_001971, Spectrum3_001930, Spectrum4_001690, Spectrum5_000340, UNII-UX3J3KK2UG, BSPBio_003530, KBioGR_001960, KBioSS_001989, DivK1c_006639, SCHEMBL308008, SPECTRUM1504071, SPBio_002121, orb1300215, orb3140351, CHEMBL1081585, HY-N0513R, KBio1_001583, KBio2_001989, KBio2_004557, KBio2_007125, KBio3_002760, JNNGEAWILNVFFD-CDJYTOATSA-N, HY-N0513, CCG-39437, AKOS032962058, EBC-617710, FL65690, SDCCGMLS-0066805.P001, Loganic acid, >=95% (LC/MS-ELSD), NCGC00178007-01, NCGC00178007-02, (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid, MS-26101, CS-0009052, S9191, C01512, Q19597767, (1S,4AS,6S,7R,7AS)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxyl, (1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-1-(beta-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylic acid, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A.ALPHA.,5,6,7,7A.ALPHA.-HEXAHYDRO-6.ALPHA.-HYDROXY-7.ALPHA.-METHYL-, EQV
Theoretical properties:
molecular_formula: C16H24O10
molecular_weight: 376.36 g/mol
exact_mass: 376.13694696 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 4
heavy_atom_count: 26
topological_polar_surface_area: 166 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Loganic acid is a cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively. It has a role as a plant metabolite. It is a glucoside, a cyclopentapyran and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a loganate.
chebi: A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[<em>c</em>]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by β-<small>D</small>-glucosyloxy, hydroxy and methyl groups respectively
chembl: LOGANIC ACID is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Loganic acid is an iridoid.  Loganic acid is synthesized from 7-deoxyloganic acid by the enzyme 7-deoxyloganic acid hydroxylase (7-DLH).  It is a substrate for the enzyme loganate O-methyltransferase for the production of loganin.