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1,3,4-TRIHYDROXY-5-(3-PHENOXYPROPYL)-CYCLOHEXANE-1-CARBOXYLIC A CID

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Identification

Generic Name
1,3,4-TRIHYDROXY-5-(3-PHENOXYPROPYL)-CYCLOHEXANE-1-CARBOXYLIC A CID
DrugBank Accession Number
DB04656
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 310.3423
Monoisotopic: 310.141638436
Chemical Formula
C16H22O6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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
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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
Phenoxy compounds / Phenol ethers / Cyclohexanols / Alkyl aryl ethers / Alpha hydroxy acids and derivatives / Tertiary alcohols / Polyols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides
show 2 more
Substituents
Alkyl aryl ether / Alpha-hydroxy acid / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclohexanol / Ether / Hydrocarbon derivative
show 10 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
SCUFESRLGCQXRX-DCDXPUDHSA-N
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
IUPAC Name
(1S,3R,4R,5S)-1,3,4-trihydroxy-5-(3-phenoxypropyl)cyclohexane-1-carboxylic acid
SMILES
[H][C@@]1(O)C[C@@](O)(C[C@]([H])(CCCOC2=CC=CC=C2)[C@@]1([H])O)C(O)=O

References

General References
Not Available
PubChem Compound
6102758
PubChem Substance
46504969
ChemSpider
4810266
ZINC
ZINC000012504452
PDBe Ligand
CA2
PDB Entries
2bt4 / 3n76

Clinical Trials

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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 Solubility4.11 mg/mLALOGPS
logP0.35ALOGPS
logP0.6Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.51Chemaxon
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area107.22 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity78.25 m3·mol-1Chemaxon
Polarizability31.83 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6007
Blood Brain Barrier-0.5099
Caco-2 permeable-0.7223
P-glycoprotein substrateSubstrate0.6631
P-glycoprotein inhibitor INon-inhibitor0.8335
P-glycoprotein inhibitor IINon-inhibitor0.6636
Renal organic cation transporterNon-inhibitor0.8206
CYP450 2C9 substrateNon-substrate0.822
CYP450 2D6 substrateNon-substrate0.8841
CYP450 3A4 substrateSubstrate0.5309
CYP450 1A2 substrateNon-inhibitor0.7921
CYP450 2C9 inhibitorNon-inhibitor0.7761
CYP450 2D6 inhibitorNon-inhibitor0.9365
CYP450 2C19 inhibitorNon-inhibitor0.7142
CYP450 3A4 inhibitorNon-inhibitor0.9262
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9518
Ames testNon AMES toxic0.8792
CarcinogenicityNon-carcinogens0.9435
BiodegradationNot ready biodegradable0.756
Rat acute toxicity2.2664 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9554
hERG inhibition (predictor II)Non-inhibitor0.5727
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/MSsplash10-0292-0794000000-7a7d7b6cba6079d2bc22
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0139000000-078465516161c3d9e0d3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1691000000-0b34174afcb5c9c4a20d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052e-2593000000-dd6c0061dedd44ea0b32
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-5391000000-eccc2cb6e9f88d620365
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-9240000000-c02c599a13a056906951
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]-170.8726
predicted
DeepCCS 1.0 (2019)
[M+H]+173.26817
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.2889
predicted
DeepCCS 1.0 (2019)

Targets

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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 11, 2007 17:49 / Updated at June 12, 2020 16:52