NAV
Explore a selection of essential drug information below, or:
Unlock enhanced features & extensive drug insights. Create a free account.
Explore the full scope of our drug knowledge tailored for pharmaceutical research needs in our data library. Learn more.

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

Explore a selection of our essential drug information below, or:

CREATE FREE ACCOUNT
Full Drug Profiles
Unlock enhanced features & extensive drug insights, including detailed interaction data & regulatory status. Create a free account.
SUBSCRIBERECOMMENDED FOR PHARMA
Data Packages
Explore the full scope of our drug knowledge tailored for pharmaceutical research needs in our data library. Learn more.

Identification

Generic Name
(1S,4S,5S)-1,4,5-TRIHYDROXY-3-[3-(PHENYLTHIO)PHENYL]CYCLOHEX-2-ENE-1-CARBOXYLIC ACID
DrugBank Accession Number
DB08485
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 358.408
Monoisotopic: 358.087494376
Chemical Formula
C19H18O5S
Synonyms
Not Available
Unlock the secrets to drugging the undruggable
Discover how groundbreaking research is turning "undruggable" targets into therapeutic opportunities.
Download eBook
Unlock the secrets to drugging the undruggable
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-dehydroquinate dehydrataseNot AvailableStreptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
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), which 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.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Quinic acids and derivatives
Alternative Parents
Diarylthioethers / Thiophenol ethers / Benzene and substituted derivatives / Alpha hydroxy acids and derivatives / Tertiary alcohols / Secondary alcohols / Sulfenyl compounds / Polyols / Monocarboxylic acids and derivatives / Carboxylic acids
show 3 more
Substituents
Alpha-hydroxy acid / Aromatic homomonocyclic compound / Aryl thioether / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Diarylthioether / Hydrocarbon derivative / Hydroxy acid
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QMNMNSINKIFYBV-LMMKCTJWSA-N
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
IUPAC Name
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-(phenylsulfanyl)phenyl]cyclohex-2-ene-1-carboxylic acid
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

References

General References
Not Available
PubChem Compound
16058682
PubChem Substance
99444956
ChemSpider
17218400
ZINC
ZINC000016051897
PDBe Ligand
RP4
PDB Entries
2cjf

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0893 mg/mLALOGPS
logP1.8ALOGPS
logP2.11Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.29Chemaxon
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area97.99 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity96.26 m3·mol-1Chemaxon
Polarizability36.7 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9619
Blood Brain Barrier-0.6943
Caco-2 permeable-0.6267
P-glycoprotein substrateSubstrate0.5371
P-glycoprotein inhibitor INon-inhibitor0.8047
P-glycoprotein inhibitor IINon-inhibitor0.969
Renal organic cation transporterNon-inhibitor0.9226
CYP450 2C9 substrateNon-substrate0.8041
CYP450 2D6 substrateNon-substrate0.8711
CYP450 3A4 substrateNon-substrate0.5705
CYP450 1A2 substrateNon-inhibitor0.8337
CYP450 2C9 inhibitorNon-inhibitor0.7167
CYP450 2D6 inhibitorNon-inhibitor0.9135
CYP450 2C19 inhibitorNon-inhibitor0.7852
CYP450 3A4 inhibitorNon-inhibitor0.9565
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7735
Ames testNon AMES toxic0.8477
CarcinogenicityNon-carcinogens0.8686
BiodegradationNot ready biodegradable0.941
Rat acute toxicity2.2084 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9976
hERG inhibition (predictor II)Non-inhibitor0.8362
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-0029000000-d9c241ab6cac39ca303e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-420f4bc4ef490cdf9065
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0749000000-99d2c4c1a72fcbfccb5d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0c04-0179000000-9ab11c2a8521934b879f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aba-5494000000-9d8a80bc53ddc3c39f51
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dr-1391000000-998c09af5d53e7ccb76b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.14317
predicted
DeepCCS 1.0 (2019)
[M+H]+185.53874
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.57597
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. 3-dehydroquinate dehydratase
Kind
Protein
Organism
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Pharmacological action
Unknown
General Function
3-dehydroquinate dehydratase activity
Specific Function
Catalyzes a trans-dehydration via an enolate intermediate.
Gene Name
aroQ
Uniprot ID
P15474
Uniprot Name
3-dehydroquinate dehydratase
Molecular Weight
16681.69 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:32 / Updated at June 12, 2020 16:52