NAV

(3Z,6S)-6-Chloro-1-(2-{[(5-chloro-1-benzothiophen-3-yl)methyl]amino}ethyl)-3-({2-[(2R)-2-piperidinyl]ethyl}imino)-2-piperazinol

Identification

Generic Name
(3Z,6S)-6-Chloro-1-(2-{[(5-chloro-1-benzothiophen-3-yl)methyl]amino}ethyl)-3-({2-[(2R)-2-piperidinyl]ethyl}imino)-2-piperazinol
DrugBank Accession Number
DB07521
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 484.485
Monoisotopic: 483.162636743
Chemical Formula
C22H31Cl2N5OS
Synonyms
  • (3S)-3-Chloro-4-[2-[(5-chloro-1-benzothiophen-3-yl)methylamino]ethyl]-6-[2-[(2R)-piperidin-2-yl]ethylamino]-3,5-dihydro-2H-pyrazin-5-ol
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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
UProthrombinNot 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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
YHTGPUXGIBWHPN-IKQMYLSPSA-N
InChI
InChI=1S/C22H31Cl2N5OS/c23-16-4-5-19-18(11-16)15(14-31-19)12-25-9-10-29-20(24)13-28-21(22(29)30)27-8-6-17-3-1-2-7-26-17/h4-5,11,14,17,20,22,25-26,30H,1-3,6-10,12-13H2,(H,27,28)/t17-,20-,22?/m1/s1
IUPAC Name
(3Z,6S)-6-chloro-1-(2-{[(5-chloro-1-benzothiophen-3-yl)methyl]amino}ethyl)-3-({2-[(2R)-piperidin-2-yl]ethyl}imino)piperazin-2-ol
SMILES
[H][C@]1(CC\N=C2/NC[C@]([H])(Cl)N(CCNCC3=CSC4=CC=C(Cl)C=C34)C2O)CCCCN1

References

General References
Not Available
PubChem Compound
131704305
PubChem Substance
99443992
ChemSpider
64873351
PDBe Ligand
C2D
PDB Entries
2bxt

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 Solubility0.00386 mg/mLALOGPS
logP2.69ALOGPS
logP3.12Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)12.21Chemaxon
pKa (Strongest Basic)10.42Chemaxon
Physiological Charge3Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area71.92 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity128.43 m3·mol-1Chemaxon
Polarizability52.15 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.891
Blood Brain Barrier-0.5596
Caco-2 permeable-0.647
P-glycoprotein substrateSubstrate0.847
P-glycoprotein inhibitor INon-inhibitor0.5327
P-glycoprotein inhibitor IIInhibitor0.8471
Renal organic cation transporterInhibitor0.5157
CYP450 2C9 substrateNon-substrate0.6413
CYP450 2D6 substrateNon-substrate0.7325
CYP450 3A4 substrateSubstrate0.5644
CYP450 1A2 substrateInhibitor0.6045
CYP450 2C9 inhibitorNon-inhibitor0.5912
CYP450 2D6 inhibitorNon-inhibitor0.527
CYP450 2C19 inhibitorInhibitor0.5376
CYP450 3A4 inhibitorNon-inhibitor0.7988
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5778
Ames testNon AMES toxic0.6147
CarcinogenicityNon-carcinogens0.9024
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5621 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8216
hERG inhibition (predictor II)Inhibitor0.856
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0000900000-650b6655b3c1a860129b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0000900000-e412ddf7f548e52498aa
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1220900000-2f00b0973619b7c96b06
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-5009500000-a03fbecd5a6548f281e4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-3910200000-980bd075ed54105a13ef
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-3324900000-4fcfeb719f013fba1ff3
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]-208.42935
predicted
DeepCCS 1.0 (2019)
[M+H]+210.82494
predicted
DeepCCS 1.0 (2019)
[M+Na]+216.73746
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]

Drug created at September 15, 2010 21:23 / Updated at June 12, 2020 16:52