Status : experimental

Chemical Classification

This compound belongs to the class of organic compounds known as quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), whis is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.

Quinic acids and derivatives

Organic compounds

Organooxygen compounds

Alcohols and polyols

Cyclic alcohols and derivatives

Calculated Property

kind Value Source
logP 0.35 ALOGPS
logS -1.9 ALOGPS
Water Solubility 4.11e+00 g/l ALOGPS
logP 0.6 ChemAxon
IUPAC Name (1S,3R,4R,5S)-1,3,4-trihydroxy-5-(3-phenoxypropyl)cyclohexane-1-carboxylic acid ChemAxon
Traditional IUPAC Name (1S,3R,4R,5S)-1,3,4-trihydroxy-5-(3-phenoxypropyl)cyclohexane-1-carboxylic acid ChemAxon
Molecular Weight 310.3423 ChemAxon
Monoisotopic Weight 310.141638436 ChemAxon
SMILES [H][C@@]1(O)C[C@@](O)(C[C@]([H])(CCCOC2=CC=CC=C2)[C@@]1([H])O)C(O)=O ChemAxon
Molecular Formula C16H22O6 ChemAxon
InChI InChI=1S/C16H22O6/c17-13-10-16(21,15(19)20)9-11(14(13)18)5-4-8-22-12-6-2-1-3-7-12/h1-3,6-7,11,13-14,17-18,21H,4-5,8-10H2,(H,19,20)/t11-,13+,14+,16-/m0/s1 ChemAxon
Polar Surface Area (PSA) 107.22 ChemAxon
Refractivity 78.25 ChemAxon
Polarizability 31.89 ChemAxon
Rotatable Bond Count 6 ChemAxon
H Bond Acceptor Count 6 ChemAxon
H Bond Donor Count 4 ChemAxon
pKa (strongest acidic) 3.51 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Target within organism

  • 3-dehydroquinate dehydratase : in Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)