1-{[(1E)-(3-HYDROXY-2-METHYL-5-{[(TRIHYDROXY-LAMBDA^5^-PHOSPHANYL)OXY]METHYL}PYRIDIN-4-YL)METHYLIDENE]AMINO}UNDECAN-2-ONE

Identification

Generic Name
1-{[(1E)-(3-HYDROXY-2-METHYL-5-{[(TRIHYDROXY-LAMBDA^5^-PHOSPHANYL)OXY]METHYL}PYRIDIN-4-YL)METHYLIDENE]AMINO}UNDECAN-2-ONE
DrugBank Accession Number
DB08364
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 416.4489
Monoisotopic: 416.20762331
Chemical Formula
C19H33N2O6P
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCAI-1 autoinducer synthaseNot AvailableVibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
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
Adverseeffects
Improve decision support & research outcomes
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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 methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Methylpyridines
Direct Parent
Methylpyridines
Alternative Parents
Hydroxypyridines / Heteroaromatic compounds / Shiff bases / Ketones / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aldimine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyridine / Imine / Ketone / Methylpyridine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VERCTSZYCODNLU-DEDYPNTBSA-N
InChI
InChI=1S/C19H33N2O6P/c1-3-4-5-6-7-8-9-10-17(22)12-20-13-18-16(14-27-28(24,25)26)11-21-15(2)19(18)23/h11,13,23-26,28H,3-10,12,14H2,1-2H3/b20-13+
IUPAC Name
hydroxy({5-hydroxy-6-methyl-4-[(1E)-[(2-oxoundecyl)imino]methyl]pyridin-3-yl}methoxy)phosphonous acid
SMILES
CCCCCCCCCC(=O)C\N=C\C1=C(COP(O)(O)O)C=NC(C)=C1O

References

General References
Not Available
PubChem Compound
46937144
PubChem Substance
99444835
ChemSpider
25057666
ZINC
ZINC000053683108
PDBe Ligand
P89
PDB Entries
2wka

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0144 mg/mLALOGPS
logP3.65ALOGPS
logP2.49ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.4ChemAxon
pKa (Strongest Basic)5.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.47 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity109.78 m3·mol-1ChemAxon
Polarizability45.2 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8009
Blood Brain Barrier+0.5746
Caco-2 permeable-0.6059
P-glycoprotein substrateSubstrate0.7238
P-glycoprotein inhibitor INon-inhibitor0.7365
P-glycoprotein inhibitor IINon-inhibitor0.8889
Renal organic cation transporterNon-inhibitor0.7156
CYP450 2C9 substrateNon-substrate0.7435
CYP450 2D6 substrateNon-substrate0.7535
CYP450 3A4 substrateSubstrate0.5055
CYP450 1A2 substrateNon-inhibitor0.7726
CYP450 2C9 inhibitorNon-inhibitor0.8067
CYP450 2D6 inhibitorNon-inhibitor0.8411
CYP450 2C19 inhibitorNon-inhibitor0.7284
CYP450 3A4 inhibitorNon-inhibitor0.7203
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8354
Ames testNon AMES toxic0.682
CarcinogenicityNon-carcinogens0.8632
BiodegradationNot ready biodegradable0.9952
Rat acute toxicity2.5871 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7888
hERG inhibition (predictor II)Non-inhibitor0.5805
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/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

Targets

Drugtargets2
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Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
Transferase activity, transferring acyl groups
Specific Function
Required for the synthesis of the quorum-sensing autoinducer CAI-1 ((S)-3-hydroxytridecan-4-one) which probably functions as an intragenus signal.
Gene Name
cqsA
Uniprot ID
Q9KM65
Uniprot Name
CAI-1 autoinducer synthase
Molecular Weight
43593.15 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 21:31 / Updated at June 12, 2020 16:52