NAV

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
Similar Structures
Weight
Average: 416.4489
Monoisotopic: 416.20762331
Chemical Formula
C19H33N2O6P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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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
1-[(E)-[(3-hydroxy-2-methyl-5-{[(trihydroxy-lambda5-phosphanyl)oxy]methyl}pyridin-4-yl)methylidene]amino]undecan-2-one
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)5.55Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area132.47 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity109.78 m3·mol-1Chemaxon
Polarizability45.25 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/MSsplash10-014j-0107900000-5ab887c0e10613425dc2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-65e7619b3aa8594af519
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1798000000-cbdbd15bcf952c79ecbc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9001200000-29b74205f028930f16c0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9001000000-0fd4d96783316d91ebd7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-9733000000-d73a037ffe6acf8d5df7
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-201.2915
predicted
DeepCCS 1.0 (2019)
[M+H]+205.11119
predicted
DeepCCS 1.0 (2019)
[M+Na]+213.92625
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. CAI-1 autoinducer synthase
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