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[(1S)-1-(5-CHLORO-1-BENZOTHIEN-3-YL)-2-(2-NAPHTHYLAMINO)-2-OXOETHYL]PHOSPHONIC ACID

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Identification

Generic Name
[(1S)-1-(5-CHLORO-1-BENZOTHIEN-3-YL)-2-(2-NAPHTHYLAMINO)-2-OXOETHYL]PHOSPHONIC ACID
DrugBank Accession Number
DB07680
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 431.829
Monoisotopic: 431.014792882
Chemical Formula
C20H15ClNO4PS
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UChymaseNot 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 naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
1-benzothiophenes / N-arylamides / Aryl chlorides / Thiophenes / Organic phosphonic acids / Heteroaromatic compounds / Secondary carboxylic acid amides / Organopnictogen compounds / Organophosphorus compounds / Organochlorides
show 3 more
Substituents
1-benzothiophene / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Benzothiophene / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative
show 16 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
HUJXISJLAPAFBO-IBGZPJMESA-N
InChI
InChI=1S/C20H15ClNO4PS/c21-14-6-8-18-16(10-14)17(11-28-18)19(27(24,25)26)20(23)22-15-7-5-12-3-1-2-4-13(12)9-15/h1-11,19H,(H,22,23)(H2,24,25,26)/t19-/m0/s1
IUPAC Name
[(S)-(5-chloro-1-benzothiophen-3-yl)[(naphthalen-2-yl)carbamoyl]methyl]phosphonic acid
SMILES
[H][C@@](C(=O)NC1=CC=C2C=CC=CC2=C1)(C1=CSC2=C1C=C(Cl)C=C2)P(O)(O)=O

References

General References
Not Available
PubChem Compound
16122567
PubChem Substance
99444151
ChemSpider
17279485
ZINC
ZINC000028604312
PDBe Ligand
DRX
PDB Entries
2hvx

Clinical Trials

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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 Solubility0.00715 mg/mLALOGPS
logP3.25ALOGPS
logP4.21Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.52Chemaxon
pKa (Strongest Basic)-9.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area86.63 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity110.86 m3·mol-1Chemaxon
Polarizability40.15 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.769
Blood Brain Barrier+0.8641
Caco-2 permeable-0.5952
P-glycoprotein substrateNon-substrate0.7909
P-glycoprotein inhibitor INon-inhibitor0.9249
P-glycoprotein inhibitor IINon-inhibitor0.907
Renal organic cation transporterNon-inhibitor0.9371
CYP450 2C9 substrateNon-substrate0.5531
CYP450 2D6 substrateNon-substrate0.8204
CYP450 3A4 substrateNon-substrate0.5989
CYP450 1A2 substrateInhibitor0.6264
CYP450 2C9 inhibitorNon-inhibitor0.6317
CYP450 2D6 inhibitorNon-inhibitor0.8763
CYP450 2C19 inhibitorNon-inhibitor0.6454
CYP450 3A4 inhibitorNon-inhibitor0.7316
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5849
Ames testNon AMES toxic0.5883
CarcinogenicityNon-carcinogens0.6114
BiodegradationNot ready biodegradable0.9842
Rat acute toxicity2.5444 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9825
hERG inhibition (predictor II)Non-inhibitor0.8174
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-MSsplash10-01ox-5943800000-b26626b4ab91a082f74c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0030900000-2e66cc771ad900d16a3e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0020900000-e041147890b60ea3a5aa
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0010900000-d1e141c40f221b5eb3f2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-3030900000-55f8eed6ec4c55a48286
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00gl-0920100000-789fd1366393fa4d048b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-9400000000-170fd9ea9a0b8cc8ccee
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]-177.87556
predicted
DeepCCS 1.0 (2019)
[M+H]+180.27113
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.28342
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Chymase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Major secreted protease of mast cells with suspected roles in vasoactive peptide generation, extracellular matrix degradation, and regulation of gland secretion
Specific Function
Endopeptidase activity
Gene Name
CMA1
Uniprot ID
P23946
Uniprot Name
Chymase
Molecular Weight
27324.56 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 21:24 / Updated at June 12, 2020 16:52