NAV

(2R,3R,4S,5R)-2-acetamido-3,4-dihydroxy-5-hydroxymethyl-piperidine

Identification

Generic Name
(2R,3R,4S,5R)-2-acetamido-3,4-dihydroxy-5-hydroxymethyl-piperidine
DrugBank Accession Number
DB03861
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 204.2236
Monoisotopic: 204.11100701
Chemical Formula
C8H16N2O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-hexosaminidase subunit betaNot AvailableHumans
UCalcium-activated potassium channel subunit beta-2Not 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
Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Amino acids and derivatives / Dialkylamines / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino acid or derivatives / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative
show 12 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
hydroxypiperidine (CHEBI:43403)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
176246-06-3
InChI Key
IWVRQJNSUOIUFV-VGRMVHKJSA-N
InChI
InChI=1S/C8H16N2O4/c1-4(12)10-8-7(14)6(13)5(3-11)2-9-8/h5-9,11,13-14H,2-3H2,1H3,(H,10,12)/t5-,6+,7+,8-/m1/s1
IUPAC Name
N-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)piperidin-2-yl]acetamide
SMILES
[H]N([C@H]1N([H])C[C@H](CO)[C@H](O)[C@@H]1O)C(C)=O

References

General References
Not Available
PubChem Compound
446429
PubChem Substance
46508888
ChemSpider
393787
PDBe Ligand
IFG
PDB Entries
1jak / 1now

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 Solubility56.1 mg/mLALOGPS
logP-1.7ALOGPS
logP-2.9Chemaxon
logS-0.56ALOGPS
pKa (Strongest Acidic)12.39Chemaxon
pKa (Strongest Basic)7.25Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area101.82 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity47.63 m3·mol-1Chemaxon
Polarizability20.14 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6052
Blood Brain Barrier-0.6893
Caco-2 permeable-0.7537
P-glycoprotein substrateSubstrate0.5452
P-glycoprotein inhibitor INon-inhibitor0.9589
P-glycoprotein inhibitor IINon-inhibitor0.936
Renal organic cation transporterNon-inhibitor0.926
CYP450 2C9 substrateNon-substrate0.7035
CYP450 2D6 substrateNon-substrate0.8103
CYP450 3A4 substrateNon-substrate0.6983
CYP450 1A2 substrateNon-inhibitor0.924
CYP450 2C9 inhibitorNon-inhibitor0.9194
CYP450 2D6 inhibitorNon-inhibitor0.9364
CYP450 2C19 inhibitorNon-inhibitor0.9258
CYP450 3A4 inhibitorNon-inhibitor0.9811
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9737
Ames testNon AMES toxic0.6228
CarcinogenicityNon-carcinogens0.9581
BiodegradationReady biodegradable0.7834
Rat acute toxicity1.8633 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.99
hERG inhibition (predictor II)Non-inhibitor0.9353
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-MSsplash10-00dr-5900000000-266ebe7bcff4ffd80282
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0970000000-9d15ec2be6e8e964a595
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0890000000-fb3cf42688be542c009a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-054o-3900000000-647b68b0117e23ace409
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ds-1900000000-645d906e14104ad2730a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052o-9200000000-a441442a23a0db6632ed
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-5d4050aec85ce60880bc
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]-146.1538
predicted
DeepCCS 1.0 (2019)
[M+H]+148.5118
predicted
DeepCCS 1.0 (2019)
[M+Na]+156.16202
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-hexosaminidase subunit beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
Gene Name
HEXB
Uniprot ID
P07686
Uniprot Name
Beta-hexosaminidase subunit beta
Molecular Weight
63110.745 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. [Article]
  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. [Article]
Details2. Calcium-activated potassium channel subunit beta-2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Potassium channel regulator activity
Specific Function
Regulatory subunit of the calcium activated potassium KCNMA1 (maxiK) channel. Modulates the calcium sensitivity and gating kinetics of KCNMA1, thereby contributing to KCNMA1 channel diversity. Acts...
Gene Name
KCNMB2
Uniprot ID
Q9Y691
Uniprot Name
Calcium-activated potassium channel subunit beta-2
Molecular Weight
27129.37 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52