(1R,2R,3R,4S,5R)-4-(Benzylamino)-5-(methylthio)cyclopentane-1,2,3-triol

Identification

Generic Name
(1R,2R,3R,4S,5R)-4-(Benzylamino)-5-(methylthio)cyclopentane-1,2,3-triol
DrugBank Accession Number
DB06984
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 269.36
Monoisotopic: 269.108564169
Chemical Formula
C13H19NO3S
Synonyms
  • Benzylation of mannostatin A, 1b

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAlpha-mannosidase 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
Adverseeffects
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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 phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylmethylamines
Alternative Parents
Benzylamines / Aminocyclitols / Aralkylamines / Cyclopentanols / 1,2-aminoalcohols / Sulfenyl compounds / Polyols / Dialkylthioethers / Dialkylamines / Organopnictogen compounds
show 1 more
Substituents
1,2-aminoalcohol / Alcohol / Amine / Aminocyclitol / Aminocyclitol or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzylamine / Cyclic alcohol / Cyclitol or derivatives
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
CHTYSDQNKZIWBZ-ZOLYEBIHSA-N
InChI
InChI=1S/C13H19NO3S/c1-18-13-9(10(15)11(16)12(13)17)14-7-8-5-3-2-4-6-8/h2-6,9-17H,7H2,1H3/t9-,10+,11+,12+,13+/m0/s1
IUPAC Name
(1R,2R,3R,4S,5R)-4-(benzylamino)-5-(methylsulfanyl)cyclopentane-1,2,3-triol
SMILES
[H]N(CC1=CC=CC=C1)[C@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@]1([H])SC

References

General References
Not Available
PubChem Compound
6914612
PubChem Substance
99443455
ChemSpider
5290492
BindingDB
84462
ZINC
ZINC000038191910
PDBe Ligand
2SK
PDB Entries
2f7p

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 Solubility5.64 mg/mLALOGPS
logP-0.01ALOGPS
logP0.24ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)7.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.72 m3·mol-1ChemAxon
Polarizability28.63 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8913
Blood Brain Barrier-0.8595
Caco-2 permeable-0.6804
P-glycoprotein substrateNon-substrate0.7236
P-glycoprotein inhibitor INon-inhibitor0.9177
P-glycoprotein inhibitor IINon-inhibitor0.7881
Renal organic cation transporterNon-inhibitor0.8561
CYP450 2C9 substrateNon-substrate0.6439
CYP450 2D6 substrateNon-substrate0.7939
CYP450 3A4 substrateNon-substrate0.6779
CYP450 1A2 substrateNon-inhibitor0.5817
CYP450 2C9 inhibitorNon-inhibitor0.7923
CYP450 2D6 inhibitorNon-inhibitor0.8874
CYP450 2C19 inhibitorNon-inhibitor0.7147
CYP450 3A4 inhibitorNon-inhibitor0.9307
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6467
Ames testNon AMES toxic0.6271
CarcinogenicityNon-carcinogens0.9172
BiodegradationNot ready biodegradable0.9141
Rat acute toxicity2.1580 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9569
hERG inhibition (predictor II)Non-inhibitor0.8839
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Details
1. Alpha-mannosidase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the first committed step in the biosynthesis of complex N-glycans. It controls conversion of high mannose to complex N-glycans; the final hydrolytic step in the N-glycan maturation pathway.
Gene Name
MAN2A1
Uniprot ID
Q16706
Uniprot Name
Alpha-mannosidase 2
Molecular Weight
131139.485 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 21:18 / Updated at June 16, 2021 12:31