(1S,4S,5S)-1,4,5-TRIHYDROXY-3-[3-(PHENYLTHIO)PHENYL]CYCLOHEX-2-ENE-1-CARBOXYLIC ACID

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 1.8 ALOGPS
logS -3.6 ALOGPS
Water Solubility 8.93e-02 g/l ALOGPS
logP 2.11 ChemAxon
IUPAC Name (1R,4R,5R)-1,4,5-trihydroxy-3-[3-(phenylsulfanyl)phenyl]cyclohex-2-ene-1-carboxylic acid ChemAxon
Traditional IUPAC Name (1R,4R,5R)-1,4,5-trihydroxy-3-[3-(phenylsulfanyl)phenyl]cyclohex-2-ene-1-carboxylic acid ChemAxon
Molecular Weight 358.408 ChemAxon
Monoisotopic Weight 358.087494376 ChemAxon
SMILES [H][C@@]1(O)C[C@@](O)(C=C(C2=CC=CC(SC3=CC=CC=C3)=C2)[C@@]1([H])O)C(O)=O ChemAxon
Molecular Formula C19H18O5S ChemAxon
InChI InChI=1S/C19H18O5S/c20-16-11-19(24,18(22)23)10-15(17(16)21)12-5-4-8-14(9-12)25-13-6-2-1-3-7-13/h1-10,16-17,20-21,24H,11H2,(H,22,23)/t16-,17-,19+/m1/s1 ChemAxon
InChIKey InChIKey=QMNMNSINKIFYBV-LMMKCTJWSA-N ChemAxon
Polar Surface Area (PSA) 97.99 ChemAxon
Refractivity 96.26 ChemAxon
Polarizability 36.7 ChemAxon
Rotatable Bond Count 4 ChemAxon
H Bond Acceptor Count 5 ChemAxon
H Bond Donor Count 4 ChemAxon
pKa (strongest acidic) 3.29 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 3 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)