NAV

1-[(4S)-4-amino-5-(1,3-benzothiazol-2-yl)-5-oxopentyl]guanidine

Identification

Generic Name
1-[(4S)-4-amino-5-(1,3-benzothiazol-2-yl)-5-oxopentyl]guanidine
DrugBank Accession Number
DB08624
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 291.372
Monoisotopic: 291.115380881
Chemical Formula
C13H17N5OS
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProthrombinNot AvailableHumans
UAryl hydrocarbon receptorNot 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 benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazoles
Sub Class
Not Available
Direct Parent
Benzothiazoles
Alternative Parents
Aryl alkyl ketones / Benzenoids / Thiazoles / Heteroaromatic compounds / Alpha-amino ketones / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
1,3-benzothiazole / Alpha-aminoketone / Amine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azole / Benzenoid / Carboximidamide
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MAJHCCQPIDXPAN-QMMMGPOBSA-N
InChI
InChI=1S/C13H17N5OS/c14-8(4-3-7-17-13(15)16)11(19)12-18-9-5-1-2-6-10(9)20-12/h1-2,5-6,8H,3-4,7,14H2,(H4,15,16,17)/t8-/m0/s1
IUPAC Name
N-[(4S)-4-amino-5-(1,3-benzothiazol-2-yl)-5-oxopentyl]guanidine
SMILES
N[C@@H](CCCNC(N)=N)C(=O)C1=NC2=CC=CC=C2S1

References

Synthesis Reference

Roger J. Hopper, Budd H. Sturm, Joseph F. Geiser, "Preparation of 2-(isopropylsulfinyl)benzothiazole." U.S. Patent US4350818, issued April, 1944.

US4350818
General References
Not Available
PubChem Compound
46937165
PubChem Substance
99445095
ChemSpider
26330359
BindingDB
50420340
ChEBI
45993
ChEMBL
CHEMBL2089125
ZINC
ZINC000053683253
PDBe Ligand
THZ
PDB Entries
8g1w

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 Solubility0.13 mg/mLALOGPS
logP0.59ALOGPS
logP0.78Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)17.79Chemaxon
pKa (Strongest Basic)12Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area117.88 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity88.29 m3·mol-1Chemaxon
Polarizability30.44 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9942
Blood Brain Barrier+0.8558
Caco-2 permeable-0.6795
P-glycoprotein substrateSubstrate0.5875
P-glycoprotein inhibitor INon-inhibitor0.9157
P-glycoprotein inhibitor IIInhibitor0.5611
Renal organic cation transporterInhibitor0.6536
CYP450 2C9 substrateNon-substrate0.8028
CYP450 2D6 substrateNon-substrate0.7009
CYP450 3A4 substrateNon-substrate0.7184
CYP450 1A2 substrateInhibitor0.6474
CYP450 2C9 inhibitorNon-inhibitor0.8101
CYP450 2D6 inhibitorNon-inhibitor0.616
CYP450 2C19 inhibitorNon-inhibitor0.7545
CYP450 3A4 inhibitorNon-inhibitor0.5133
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6243
Ames testNon AMES toxic0.7459
CarcinogenicityNon-carcinogens0.9624
BiodegradationNot ready biodegradable0.9452
Rat acute toxicity2.5910 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.953
hERG inhibition (predictor II)Non-inhibitor0.8652
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-MSsplash10-03di-6910000000-a4c59d143831f41f2692
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-f37679539620d48a1231
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0159-0090000000-db02eca29e836b535095
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000t-0090000000-00f05f5959bd66449f69
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-044u-2960000000-75ebdc18d002cf85995a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0490000000-23b6831ad301b01cabb6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-613b582f7caf9229b118
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]-158.36269
predicted
DeepCCS 1.0 (2019)
[M+H]+160.72069
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.81383
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Prothrombin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thrombospondin receptor activity
Specific Function
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostas...
Gene Name
F2
Uniprot ID
P00734
Uniprot Name
Prothrombin
Molecular Weight
70036.295 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]
Details2. Aryl hydrocarbon receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. Noguerol TN, Boronat S, Casado M, Raldua D, Barcelo D, Pina B: Evaluating the interactions of vertebrate receptors with persistent pollutants and antifouling pesticides using recombinant yeast assays. Anal Bioanal Chem. 2006 Jul;385(6):1012-9. Epub 2006 May 17. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52