(3AR,5R,6S,7R,7AR)-5-(HYDROXYMETHYL)-2-PROPYL-5,6,7,7A-TETRAHYDRO-3AH-PYRANO[3,2-D][1,3]THIAZOLE-6,7-DIOL

Identification

Generic Name
(3AR,5R,6S,7R,7AR)-5-(HYDROXYMETHYL)-2-PROPYL-5,6,7,7A-TETRAHYDRO-3AH-PYRANO[3,2-D][1,3]THIAZOLE-6,7-DIOL
DrugBank Accession Number
DB08255
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 247.311
Monoisotopic: 247.087828727
Chemical Formula
C10H17NO4S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UO-GlcNAcase BT_4395Not AvailableBacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
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 monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Monosaccharides
Alternative Parents
Oxanes / Thiazolines / Monothioacetals / Secondary alcohols / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds
show 1 more
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Azacycle / Hydrocarbon derivative / Meta-thiazoline / Monosaccharide / Monothioacetal / Organic 1,3-dipolar compound / Organic nitrogen compound / Organoheterocyclic compound
show 7 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
pyranothiazole (CHEBI:44187)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QWOPEBCGKASVQP-QXOHVQIXSA-N
InChI
InChI=1S/C10H17NO4S/c1-2-3-6-11-7-9(14)8(13)5(4-12)15-10(7)16-6/h5,7-10,12-14H,2-4H2,1H3/t5-,7-,8-,9-,10-/m1/s1
IUPAC Name
(3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-propyl-3aH,5H,6H,7H,7aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
SMILES
[H][C@]12O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])N=C(CCC)S2

References

General References
Not Available
PubChem Compound
11507040
PubChem Substance
99444726
ChemSpider
9681837
BindingDB
50323696
ChEMBL
CHEMBL1213604
ZINC
ZINC000016052203
PDBe Ligand
NB1
PDB Entries
2j4g

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 Solubility6.23 mg/mLALOGPS
logP-0.2ALOGPS
logP-0.22Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.81Chemaxon
pKa (Strongest Basic)2.38Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area82.28 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity59.53 m3·mol-1Chemaxon
Polarizability25.24 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6934
Blood Brain Barrier-0.7253
Caco-2 permeable-0.6624
P-glycoprotein substrateSubstrate0.5353
P-glycoprotein inhibitor INon-inhibitor0.9276
P-glycoprotein inhibitor IINon-inhibitor0.989
Renal organic cation transporterNon-inhibitor0.7666
CYP450 2C9 substrateNon-substrate0.782
CYP450 2D6 substrateNon-substrate0.7643
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.6419
CYP450 2C9 inhibitorNon-inhibitor0.7091
CYP450 2D6 inhibitorNon-inhibitor0.8787
CYP450 2C19 inhibitorNon-inhibitor0.7182
CYP450 3A4 inhibitorNon-inhibitor0.9718
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7774
Ames testNon AMES toxic0.5672
CarcinogenicityNon-carcinogens0.9531
BiodegradationNot ready biodegradable0.895
Rat acute toxicity2.3345 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9556
hERG inhibition (predictor II)Non-inhibitor0.9138
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-MSsplash10-05ul-9430000000-6621d1445d43b94c21ea
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-db0639df7988dce99ca4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0adi-9610000000-91335c2b4a0758a2ad01
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0032-0790000000-de918f6236d18ef22d9e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ab9-8910000000-31cd067abe419109fb93
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0059-1900000000-c5246aa9756112349cca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-8910000000-50a7163417a883372077
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]-162.4535
predicted
DeepCCS 1.0 (2019)
[M+H]+164.34892
predicted
DeepCCS 1.0 (2019)
[M+Na]+170.39455
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Pharmacological action
Unknown
General Function
Beta-n-acetylglucosaminidase activity
Specific Function
Can hydrolyze the glycosidic link of O-GlcNAcylated proteins. Can use p-nitrophenyl-beta-GlcNAc and 4-methylumbelliferone-GlcNAc as substrates (in vitro).
Gene Name
Not Available
Uniprot ID
Q89ZI2
Uniprot Name
O-GlcNAcase BT_4395
Molecular Weight
84484.62 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