Nelfinavir mesylate (CHEM017401)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:18:41 UTC
Update Date2016-11-09 01:15:35 UTC
Accession NumberCHEM017401
Identification
Common NameNelfinavir mesylate
ClassSmall Molecule
DescriptionA methanesulfonate (mesylate) salt prepared from equimolar amounts of nelfinavir and methanesulfonic acid. It is used for treatment of HIV and also exhibits some anticancer properties.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Nelfinavir mesilateChEBI
ViraceptChEBI
Nelfinavir mesilic acidGenerator
Nelfinavir mesylic acidGenerator
Mesylate, nelfinavirMeSH
Roche brand OF nelfinavir mesylateMeSH
Monomethane sulfonate, nelfinavirMeSH
Agouron brand OF nelfinavir mesylateMeSH
Nelfinavir monomethane sulfonateMeSH
NelfinavirMeSH
Sulfonate, nelfinavir monomethaneMeSH
Chemical FormulaC33H49N3O7S2
Average Molecular Mass663.890 g/mol
Monoisotopic Mass663.301 g/mol
CAS Registry Number159989-65-8
IUPAC Name(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-{[hydroxy(3-hydroxy-2-methylphenyl)methylidene]amino}-4-(phenylsulfanyl)butyl]-decahydroisoquinoline-3-carboximidic acid; methanesulfonic acid
Traditional Namemethanesulfonic acid; nelfinavir mesilate
SMILESCS(O)(=O)=O.[H][C@@](O)(CN1C[C@@]2([H])CCCC[C@@]2([H])C[C@@]1([H])C(O)=NC(C)(C)C)[C@]([H])(CSC1=CC=CC=C1)N=C(O)C1=C(C)C(O)=CC=C1
InChI IdentifierInChI=1S/C32H45N3O4S.CH4O3S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4;1-5(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39);1H3,(H,2,3,4)/t22-,23+,26-,27-,29+;/m0./s1
InChI KeyNQHXCOAXSHGTIA-SKXNDZRYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenesulfonyl group
  • Aralkylamine
  • Monocyclic benzene moiety
  • Substituted pyrrole
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrole
  • Pyrrolidine
  • Sulfone
  • Sulfonyl
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Hydrobromide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP4.68ALOGPS
logP3.88ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area108.88 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity163.72 m³·mol⁻¹ChemAxon
Polarizability64.1 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-8aec383e385658aae3bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-8aec383e385658aae3bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000009000-8aec383e385658aae3bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-009a3296752a0c20cdd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000009000-009a3296752a0c20cdd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000009000-009a3296752a0c20cdd4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000885
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNelfinavir
Chemspider IDNot Available
ChEBI ID7497
PubChem Compound ID64142
Kegg Compound IDC08091
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10452644
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10698844
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11106345
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16189129
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16545536
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17046010
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18430402
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19443141
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19660105
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=20399586
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21392920
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23385634
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=9397180
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=9607830