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Identification
NameN-(Sulfanylacetyl)Tyrosylprolylmethioninamide
Accession NumberDB01883  (EXPT02874)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 482.617
Monoisotopic: 482.16576147
Chemical FormulaC21H30N4O5S2
InChI KeyLNLWXWOYQHAKTD-ULQDDVLXSA-N
InChI
InChI=1S/C21H30N4O5S2/c1-32-10-8-15(19(22)28)24-20(29)17-3-2-9-25(17)21(30)16(23-18(27)12-31)11-13-4-6-14(26)7-5-13/h4-7,15-17,26,31H,2-3,8-12H2,1H3,(H2,22,28)(H,23,27)(H,24,29)/t15-,16-,17-/m0/s1
IUPAC Name
(2S)-2-{[(2S)-1-[(2S)-3-(4-hydroxyphenyl)-2-(2-sulfanylacetamido)propanoyl]pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanamide
SMILES
[H][C@@](CCSC)(NC(=O)[C@]1([H])CCCN1C(=O)[C@]([H])(CC1=CC=C(O)C=C1)NC(=O)CS)C(N)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Lethal factorProteinunknownNot AvailableBacillus anthracisP15917 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9754
Blood Brain Barrier-0.8551
Caco-2 permeable-0.7844
P-glycoprotein substrateSubstrate0.8621
P-glycoprotein inhibitor INon-inhibitor0.9504
P-glycoprotein inhibitor IINon-inhibitor0.9775
Renal organic cation transporterNon-inhibitor0.8167
CYP450 2C9 substrateNon-substrate0.8301
CYP450 2D6 substrateNon-substrate0.71
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9716
CYP450 2C9 inhibitorNon-inhibitor0.8714
CYP450 2D6 inhibitorNon-inhibitor0.8954
CYP450 2C19 inhibitorNon-inhibitor0.7839
CYP450 3A4 inhibitorNon-inhibitor0.9719
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9891
Ames testNon AMES toxic0.9041
CarcinogenicityNon-carcinogens0.934
BiodegradationNot ready biodegradable0.9488
Rat acute toxicity2.4015 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8601
hERG inhibition (predictor II)Non-inhibitor0.7486
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0197 mg/mLALOGPS
logP1.31ALOGPS
logP-0.14ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.17ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.83 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity125.56 m3·mol-1ChemAxon
Polarizability49.33 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Phenylpropylamine
  • Amphetamine or derivatives
  • N-substituted-alpha-amino acid
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Phenol
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Bacillus anthracis
Pharmacological action
unknown
General Function:
Metallopeptidase activity
Specific Function:
One of the three proteins composing the anthrax toxin, the agent which infects many mammalian species and that may cause death. LF is the lethal factor that, when associated with PA, causes death. LF is not toxic by itself. It is a protease that cleaves the N-terminal of most dual specificity mitogen-activated protein kinase kinases (MAPKKs or MAP2Ks) (except for MAP2K5). Cleavage invariably oc...
Gene Name:
lef
Uniprot ID:
P15917
Molecular Weight:
93769.58 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. 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. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23