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(2R,3R,4R,5S)-2-(HYDROXYMETHYL)-1-NONYLPIPERIDINE-3,4,5-TRIOL

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Data Packages
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Identification

Generic Name
(2R,3R,4R,5S)-2-(HYDROXYMETHYL)-1-NONYLPIPERIDINE-3,4,5-TRIOL
DrugBank Accession Number
DB08283
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 289.4109
Monoisotopic: 289.225308485
Chemical Formula
C15H31NO4
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
ULysosomal acid glucosylceramidaseNot AvailableHumans
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 piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Not Available
Direct Parent
Piperidines
Alternative Parents
Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Polyols / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1,2-aminoalcohol / Alcohol / Aliphatic heteromonocyclic compound / Amine / Azacycle / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
tertiary amino compound, hydroxypiperidine (CHEBI:76399)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FTSCEGKYKXESFF-LXTVHRRPSA-N
InChI
InChI=1S/C15H31NO4/c1-2-3-4-5-6-7-8-9-16-10-13(18)15(20)14(19)12(16)11-17/h12-15,17-20H,2-11H2,1H3/t12-,13+,14-,15-/m1/s1
IUPAC Name
(2R,3R,4R,5S)-2-(hydroxymethyl)-1-nonylpiperidine-3,4,5-triol
SMILES
[H][C@]1(O)CN(CCCCCCCCC)[C@]([H])(CO)[C@@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
501640
PubChem Substance
99444754
ChemSpider
438794
BindingDB
18358
ChEBI
76399
ChEMBL
CHEMBL408500
ZINC
ZINC000014253608
PDBe Ligand
NND
PDB Entries
2v3e

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 Solubility9.58 mg/mLALOGPS
logP1.3ALOGPS
logP1.04Chemaxon
logS-1.5ALOGPS
pKa (Strongest Acidic)12.9Chemaxon
pKa (Strongest Basic)8.37Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area84.16 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity78.75 m3·mol-1Chemaxon
Polarizability34.57 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.877
Blood Brain Barrier-0.9092
Caco-2 permeable-0.6339
P-glycoprotein substrateSubstrate0.8106
P-glycoprotein inhibitor INon-inhibitor0.6446
P-glycoprotein inhibitor IINon-inhibitor0.9289
Renal organic cation transporterNon-inhibitor0.7472
CYP450 2C9 substrateNon-substrate0.8316
CYP450 2D6 substrateNon-substrate0.7471
CYP450 3A4 substrateNon-substrate0.5581
CYP450 1A2 substrateNon-inhibitor0.9112
CYP450 2C9 inhibitorNon-inhibitor0.9
CYP450 2D6 inhibitorNon-inhibitor0.9159
CYP450 2C19 inhibitorNon-inhibitor0.9383
CYP450 3A4 inhibitorNon-inhibitor0.9749
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9935
Ames testNon AMES toxic0.8383
CarcinogenicityNon-carcinogens0.9587
BiodegradationNot ready biodegradable0.6063
Rat acute toxicity2.1798 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6812
hERG inhibition (predictor II)Non-inhibitor0.8208
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00dj-6970000000-1af3e72bd55e70bd29b3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-8eea61fda19aa229f0dd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-666a321f430b4a0914fe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0190000000-a51b0240d6b9faa5ebe0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0596-2590000000-2bf38d7284cc433b1b9e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06sc-9850000000-4c70646fe32927673254
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9510000000-69e6177d065ea9bc14ed
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]-190.0500755
predicted
DarkChem Lite v0.1.0
[M-H]-175.3776
predicted
DeepCCS 1.0 (2019)
[M+H]+190.8947755
predicted
DarkChem Lite v0.1.0
[M+H]+178.82996
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.4374755
predicted
DarkChem Lite v0.1.0
[M+Na]+187.30821
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Lysosomal acid glucosylceramidase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Glucosylceramidase that catalyzes, within the lysosomal compartment, the hydrolysis of glucosylceramides/GlcCers (such as beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine) into free ceramides (such as N-acylsphing-4-enine) and glucose (PubMed:15916907, PubMed:24211208, PubMed:32144204, PubMed:9201993). Plays a central role in the degradation of complex lipids and the turnover of cellular membranes (PubMed:27378698). Through the production of ceramides, participates in the PKC-activated salvage pathway of ceramide formation (PubMed:19279011). Catalyzes the glucosylation of cholesterol, through a transglucosylation reaction where glucose is transferred from GlcCer to cholesterol (PubMed:24211208, PubMed:26724485, PubMed:32144204). GlcCer containing mono-unsaturated fatty acids (such as beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4-enine) are preferred as glucose donors for cholesterol glucosylation when compared with GlcCer containing same chain length of saturated fatty acids (such as beta-D-glucosyl-N-octadecanoyl-sphing-4-enine) (PubMed:24211208). Under specific conditions, may alternatively catalyze the reverse reaction, transferring glucose from cholesteryl 3-beta-D-glucoside to ceramide (Probable) (PubMed:26724485). Can also hydrolyze cholesteryl 3-beta-D-glucoside producing glucose and cholesterol (PubMed:24211208, PubMed:26724485). Catalyzes the hydrolysis of galactosylceramides/GalCers (such as beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine), as well as the transfer of galactose between GalCers and cholesterol in vitro, but with lower activity than with GlcCers (PubMed:32144204). Contrary to GlcCer and GalCer, xylosylceramide/XylCer (such as beta-D-xyosyl-(1<->1')-N-acylsphing-4-enine) is not a good substrate for hydrolysis, however it is a good xylose donor for transxylosylation activity to form cholesteryl 3-beta-D-xyloside (PubMed:33361282)
Specific Function
galactosylceramidase activity
Gene Name
GBA1
Uniprot ID
P04062
Uniprot Name
Lysosomal acid glucosylceramidase
Molecular Weight
59715.745 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 21:30 / Updated at June 12, 2020 16:52