NAV

[N-(BENZYLOXYCARBONYL)AMINO](4-AMIDINOPHENYL)METHANE-PHOSPHONATE

Identification

Generic Name
[N-(BENZYLOXYCARBONYL)AMINO](4-AMIDINOPHENYL)METHANE-PHOSPHONATE
DrugBank Accession Number
DB08763
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 363.305
Monoisotopic: 363.098407213
Chemical Formula
C16H18N3O5P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTrypsin-1Not 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 benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzyloxycarbonyls
Direct Parent
Benzyloxycarbonyls
Alternative Parents
Organic phosphonic acids / Carbamate esters / Organic carbonic acids and derivatives / Carboximidamides / Carboxamidines / Organopnictogen compounds / Organophosphorus compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Amidine / Aromatic homomonocyclic compound / Benzyloxycarbonyl / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboximidamide / Carboxylic acid amidine / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FSNDLCSOLUMYRH-OAHLLOKOSA-N
InChI
InChI=1S/C16H18N3O5P/c17-14(18)12-6-8-13(9-7-12)15(25(21,22)23)19-16(20)24-10-11-4-2-1-3-5-11/h1-9,15H,10H2,(H3,17,18)(H,19,20)(H2,21,22,23)/t15-/m1/s1
IUPAC Name
[(R)-{[(benzyloxy)carbonyl]amino}(4-carbamimidoylphenyl)methyl]phosphonic acid
SMILES
[H][C@](NC(=O)OCC1=CC=CC=C1)(C1=CC=C(C=C1)C(N)=N)P(O)(O)=O

References

General References
Not Available
PubChem Compound
447110
PubChem Substance
99445234
ChemSpider
394295
ZINC
ZINC000031260847
PDBe Ligand
ZAP
PDB Entries
1max / 1may

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 Solubility0.0262 mg/mLALOGPS
logP0.02ALOGPS
logP0.9Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)1.41Chemaxon
pKa (Strongest Basic)11.48Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area145.73 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity102.3 m3·mol-1Chemaxon
Polarizability35.3 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9335
Blood Brain Barrier+0.91
Caco-2 permeable-0.6615
P-glycoprotein substrateNon-substrate0.6787
P-glycoprotein inhibitor INon-inhibitor0.9525
P-glycoprotein inhibitor IINon-inhibitor0.9591
Renal organic cation transporterNon-inhibitor0.9042
CYP450 2C9 substrateNon-substrate0.682
CYP450 2D6 substrateNon-substrate0.8207
CYP450 3A4 substrateNon-substrate0.7153
CYP450 1A2 substrateNon-inhibitor0.7264
CYP450 2C9 inhibitorNon-inhibitor0.8212
CYP450 2D6 inhibitorNon-inhibitor0.8712
CYP450 2C19 inhibitorNon-inhibitor0.8292
CYP450 3A4 inhibitorNon-inhibitor0.7934
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9488
Ames testNon AMES toxic0.5754
CarcinogenicityNon-carcinogens0.8001
BiodegradationNot ready biodegradable0.9839
Rat acute toxicity2.3851 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9922
hERG inhibition (predictor II)Non-inhibitor0.8898
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-MSsplash10-0006-9871000000-1a07eed41ec3c7991913
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-2089000000-0e27697acb93cdec7006
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-8290000000-67183614dc9a6a5181af
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dm-2294000000-5f97ac107fccbf16da27
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-9040000000-ba7f5a9cc214daa939c5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9801000000-22fe333cf4f4f8e87391
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-9000000000-2aef0b4d0ba102f5a0a9
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]-174.43326
predicted
DeepCCS 1.0 (2019)
[M+H]+176.79124
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.58382
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Trypsin-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-1
Molecular Weight
26557.88 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 21:34 / Updated at June 12, 2020 16:52