Compound: shikimic acid
SMILES: O=C(O)C1=C[C@@H](O)[C@@H](O)[C@@H](C1)O
InChIKey: JXOHGGNKMLTUBP-HSUXUTPPSA-N
Synonyms: shikimic acid, 138-59-0, (3R,4S,5R)-3,4,5-TRIHYDROXYCYCLOHEX-1-ENE-1-CARBOXYLIC ACID, 1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)-, (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid, 3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid, Bracken fern toxic component, 29MS2WI2NU, VEROCHIC, DTXSID4032039, 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))-, 3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid, CHEBI:16119, NSC-59257, Acid, Shikimic, Shikimic Acid Derivatives, RefChem:885013, DTXCID2012039, 205-334-2, L-Shikimic acid, (-)-Shikimic acid, (3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid, ShikimicAcid, CCRIS 7681, HSDB 3537, MFCD00066278, 106210-02-0, CHEMBL290345, HYDROTRIS(3-PHENYLPYRAZOL-1-YL)BORATE THALLIUM SALT, [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid, (3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid, (-)-Shikimate, (4S,3R,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid, SMR001306700, SR-01000632403, EINECS 205-334-2, NSC 59257, UNII-29MS2WI2NU, Skikimate, NSC59257, L-Shikimate, 2aay, 4guj, Spectrum_001232, 1we2, 2aa9, SpecPlus_000488, Spectrum2_001508, Spectrum3_001541, Spectrum4_001853, Spectrum5_000386, Shikimic acid (Standard), 1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, Shikimic acid, >=99%, bmse000114, EC 205-334-2, SHIKIMIC ACID [MI], SCHEMBL43377, BSPBio_002982, KBioGR_002287, KBioSS_001712, SHIKIMIC ACID [HSDB], SHIKIMIC ACID [IARC], MLS002207031, MLS004256600, DivK1c_006584, SPECTRUM1502256, SPBio_001555, MEGxp0_001939, HY-N0130R, KBio1_001528, KBio2_001712, KBio2_004280, KBio2_006848, KBio3_002482, Shikimic acid, analytical standard, (3r,4s,5r)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid, HY-N0130, MSK40056, BDBM50281998, CCG-38884, EBC-13807, SBB012371, AKOS004119897, AC-8010, FS06909, SDCCGMLS-0066740.P001, SMP1_000326, NCGC00142601-01, NCGC00142601-02, AS-13905, ST069316, SY057997, CS-0007856, NS00079355, S0038, C00493, EN300-208879, F037802, Q410830, SR-01000632403-1, SR-01000632403-4, SR-01000632403-5, (-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid, Z1198149969, (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylicacid, B1A53F8A-8664-405D-8370-A9785ADD2D0B, (3R,4S,5R))-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid, (3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid, 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- (9CI), SHIKIMIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC], [3R-(3 alpha,4 alpha,5 beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid, 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta)), 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))- (9CI), 3,4,5-Trihydroxy-, [3R-3.alpha.,4.alpha.,5.beta. )]-, 1-cyclohexene-1-carboxylic acid, Shikimic acid [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid, InChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s
Theoretical properties:
molecular_formula: C7H10O5
molecular_weight: 174.15 g/mol
exact_mass: 174.05282342 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 1
heavy_atom_count: 12
topological_polar_surface_area: 98 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Needles from methanol/ethyl acetate
color: Needles from methanol/ethyl acetate
melting_point: 183-184.5 °C
solubility: Water solubility = 1.5X10+5 mg/l @ 21 °C
vapor_pressure: 0.00000001 [mmHg]
Descriptions:
pubchem: Shikimic acid is a cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms. It has a role as a Saccharomyces cerevisiae metabolite, a plant metabolite and an Escherichia coli metabolite. It is a cyclohexenecarboxylic acid, a hydroxy monocarboxylic acid and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a shikimate.
chebi: A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3<i>R</i>,4<i>S</i>,5<i>R</i> stereoisomer). It is an intermediate metabolite in plants and microorganisms.
chembl: SHIKIMIC ACID is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later.