NAV

N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONAMIDE

Identification

Generic Name
N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONAMIDE
DrugBank Accession Number
DB07527
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 392.512
Monoisotopic: 392.176978084
Chemical Formula
C20H28N2O4S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylbutylamines
Direct Parent
Phenylbutylamines
Alternative Parents
Amphetamines and derivatives / Benzenesulfonamides / Benzenesulfonyl compounds / Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / Aralkylamines / Organosulfonamides / Aminosulfonyl compounds
show 6 more
Substituents
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aminosulfonyl compound / Amphetamine or derivatives / Anisole / Aralkylamine / Aromatic homomonocyclic compound / Benzenesulfonamide
show 21 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
HORGTFOBJRCVMO-ZWKOTPCHSA-N
InChI
InChI=1S/C20H28N2O4S/c1-13-10-19(26-4)14(2)15(3)20(13)27(24,25)22-12-18(23)17(21)11-16-8-6-5-7-9-16/h5-10,17-18,22-23H,11-12,21H2,1-4H3/t17-,18+/m0/s1
IUPAC Name
N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-4-methoxy-2,3,6-trimethylbenzene-1-sulfonamide
SMILES
[H][C@](N)(CC1=CC=CC=C1)[C@]([H])(O)CNS(=O)(=O)C1=C(C)C=C(OC)C(C)=C1C

References

General References
Not Available
PubChem Compound
9543487
PubChem Substance
99443998
ChemSpider
7822439
BindingDB
12586
ChEMBL
CHEMBL379692
ZINC
ZINC000013681953
PDBe Ligand
C4M
PDB Entries
2c93

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 Solubility0.0236 mg/mLALOGPS
logP1.21ALOGPS
logP2.74Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)10.91Chemaxon
pKa (Strongest Basic)9.01Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area101.65 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity107.65 m3·mol-1Chemaxon
Polarizability42.73 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9524
Blood Brain Barrier-0.7247
Caco-2 permeable-0.6656
P-glycoprotein substrateSubstrate0.5436
P-glycoprotein inhibitor INon-inhibitor0.8278
P-glycoprotein inhibitor IINon-inhibitor0.8989
Renal organic cation transporterNon-inhibitor0.8874
CYP450 2C9 substrateNon-substrate0.6412
CYP450 2D6 substrateNon-substrate0.7548
CYP450 3A4 substrateSubstrate0.5415
CYP450 1A2 substrateNon-inhibitor0.7915
CYP450 2C9 inhibitorNon-inhibitor0.5637
CYP450 2D6 inhibitorNon-inhibitor0.8887
CYP450 2C19 inhibitorNon-inhibitor0.5588
CYP450 3A4 inhibitorNon-inhibitor0.5223
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6166
Ames testNon AMES toxic0.6425
CarcinogenicityNon-carcinogens0.721
BiodegradationNot ready biodegradable0.9967
Rat acute toxicity2.3711 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9325
hERG inhibition (predictor II)Non-inhibitor0.597
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-MSsplash10-00dl-3971000000-3743bb240900c7a15a62
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-1869000000-e7984c6712b62abaa70d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0039000000-2c1bb84c84a0792e9401
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00mk-2911000000-7ab45bf2b8b19b3a13b0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ov-0924000000-e1ebac29e3a93a3758ac
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gj1-2911000000-f645d760541f854b0a16
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-2902000000-c87f9e0c79918db1213d
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]-183.44284
predicted
DeepCCS 1.0 (2019)
[M+H]+185.83841
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.75095
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