NAV

2-Hydroxymethyl-Pyrrolidine-3,4-Diol

Identification

Generic Name
2-Hydroxymethyl-Pyrrolidine-3,4-Diol
DrugBank Accession Number
DB03411
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 133.1457
Monoisotopic: 133.073893223
Chemical Formula
C5H11NO3
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
UPurine nucleoside phosphorylaseNot AvailableMycobacterium tuberculosis
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 pyrrolidines. These are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
Not Available
Direct Parent
Pyrrolidines
Alternative Parents
Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / 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
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Z330X18GMD
CAS number
Not Available
InChI Key
OQEBIHBLFRADNM-YUPRTTJUSA-N
InChI
InChI=1S/C5H11NO3/c7-2-3-5(9)4(8)1-6-3/h3-9H,1-2H2/t3-,4-,5-/m0/s1
IUPAC Name
(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol
SMILES
OC[C@@H]1NC[C@H](O)[C@H]1O

References

General References
Not Available
PubChem Compound
127716
PubChem Substance
46504688
ChemSpider
113295
BindingDB
50375511
ChEMBL
CHEMBL406973
ZINC
ZINC000001492251
PDBe Ligand
EDG
PDB Entries
2ydp / 2ydt / 5jox / 6f1j / 6zq1

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 Solubility659.0 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.3Chemaxon
logS0.69ALOGPS
pKa (Strongest Acidic)13.32Chemaxon
pKa (Strongest Basic)9.36Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area72.72 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity30.61 m3·mol-1Chemaxon
Polarizability13.1 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9536
Blood Brain Barrier-0.5875
Caco-2 permeable-0.7021
P-glycoprotein substrateNon-substrate0.5191
P-glycoprotein inhibitor INon-inhibitor0.9083
P-glycoprotein inhibitor IINon-inhibitor0.8985
Renal organic cation transporterNon-inhibitor0.7737
CYP450 2C9 substrateNon-substrate0.8692
CYP450 2D6 substrateNon-substrate0.7066
CYP450 3A4 substrateNon-substrate0.7236
CYP450 1A2 substrateNon-inhibitor0.9102
CYP450 2C9 inhibitorNon-inhibitor0.9461
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9424
CYP450 3A4 inhibitorNon-inhibitor0.9954
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9796
Ames testNon AMES toxic0.844
CarcinogenicityNon-carcinogens0.9474
BiodegradationNot ready biodegradable0.8116
Rat acute toxicity1.8442 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8692
hERG inhibition (predictor II)Non-inhibitor0.8934
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-MSsplash10-0fk9-9300000000-17669072607076d2d428
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-7900000000-bae26f522616c94c6cd4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-90cc74f58ae8cffff0be
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9100000000-9c6c5f363c0a28e343f1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kal-9300000000-f75567f89febbb189f7b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-9000000000-6c2d15c72485df3c0d32
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pbc-9200000000-84495cd1fffec9024046
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]-124.9715065
predicted
DarkChem Lite v0.1.0
[M-H]-128.72734
predicted
DeepCCS 1.0 (2019)
[M+H]+125.4302065
predicted
DarkChem Lite v0.1.0
[M+H]+130.90297
predicted
DeepCCS 1.0 (2019)
[M+Na]+124.6436065
predicted
DarkChem Lite v0.1.0
[M+Na]+138.31892
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Purine nucleoside phosphorylase
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate. Cleaves guanosine, inosine, 2'-deoxyguanosine and 2'-deoxyinosine.
Specific Function
Purine-nucleoside phosphorylase activity
Gene Name
punA
Uniprot ID
P9WP01
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
27571.215 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]

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