3-Dehydroshikimate

Identification

Name
3-Dehydroshikimate
Accession Number
DB04347  (EXPT01191)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 172.1354
Monoisotopic: 172.037173366
Chemical Formula
C7H8O5
InChI Key
SLWWJZMPHJJOPH-PHDIDXHHSA-N
InChI
InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1
IUPAC Name
(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
SMILES
O[C@@H]1CC(=CC(=O)[C@H]1O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-dehydroquinate dehydrataseNot AvailableStaphylococcus aureus (strain MRSA252)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C02637
PubChem Compound
439774
PubChem Substance
46507545
ChemSpider
388830
ChEBI
30918
HET
3DS
Wikipedia
3-Dehydroshikimic_acid
PDB Entries
3n59 / 4gug / 4guh

Clinical Trials

Clinical Trials
Not Available

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 Solubility137.0 mg/mLALOGPS
logP-1.2ALOGPS
logP-1ChemAxon
logS-0.1ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.19 m3·mol-1ChemAxon
Polarizability14.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8153
Blood Brain Barrier-0.5791
Caco-2 permeable-0.7735
P-glycoprotein substrateNon-substrate0.5902
P-glycoprotein inhibitor INon-inhibitor0.9526
P-glycoprotein inhibitor IINon-inhibitor0.9974
Renal organic cation transporterNon-inhibitor0.9388
CYP450 2C9 substrateNon-substrate0.8455
CYP450 2D6 substrateNon-substrate0.9011
CYP450 3A4 substrateNon-substrate0.6261
CYP450 1A2 substrateNon-inhibitor0.9537
CYP450 2C9 inhibitorNon-inhibitor0.964
CYP450 2D6 inhibitorNon-inhibitor0.9488
CYP450 2C19 inhibitorNon-inhibitor0.965
CYP450 3A4 inhibitorNon-inhibitor0.941
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9773
Ames testNon AMES toxic0.8957
CarcinogenicityNon-carcinogens0.9479
BiodegradationReady biodegradable0.8661
Rat acute toxicity1.7570 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9814
hERG inhibition (predictor II)Non-inhibitor0.9628
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
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-001r-4951000000-73e5d4c38702a9a74934
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-05as-2981000000-48228f5a995cc5391fde
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , negativeLC-MS/MSsplash10-056r-1900000000-78f25cc3fd642b56e1ec
MS/MS Spectrum - , positiveLC-MS/MSsplash10-022i-2900000000-0cfcedb79843656d9142

Taxonomy

Description
This compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Cyclohexenones
Alternative Parents
Secondary alcohols / 1,2-diols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Cyclohexenone / Secondary alcohol / 1,2-diol / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxide / Hydrocarbon derivative / Alcohol / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
alpha,beta-unsaturated monocarboxylic acid, 4-oxo monocarboxylic acid, 5-hydroxy monocarboxylic acid, 4-hydroxy monocarboxylic acid (CHEBI:30918)

Targets

Kind
Protein
Organism
Staphylococcus aureus (strain MRSA252)
Pharmacological action
Unknown
General Function
3-dehydroquinate dehydratase activity
Specific Function
Involved in the third step of the chorismate pathway, which leads to the biosynthesis of aromatic amino acids. Catalyzes the cis-dehydration of 3-dehydroquinate (DHQ) and introduces the first doubl...
Gene Name
aroD
Uniprot ID
Q6GII7
Uniprot Name
3-dehydroquinate dehydratase
Molecular Weight
27052.965 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:55