N-(Sulfanylacetyl)Tyrosylprolylmethioninamide

Identification

Name
N-(Sulfanylacetyl)Tyrosylprolylmethioninamide
Accession Number
DB01883  (EXPT02874)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 482.617
Monoisotopic: 482.16576147
Chemical Formula
C21H30N4O5S2
InChI Key
LNLWXWOYQHAKTD-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][[email protected]@](CCSC)(NC(=O)[[email protected]]1([H])CCCN1C(=O)[[email protected]]([H])(CC1=CC=C(O)C=C1)NC(=O)CS)C(N)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULethal factorNot AvailableBacillus anthracis
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5289343
PubChem Substance
46506367
ChemSpider
4451333
HET
SD2
PDB Entries
1pwq

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0197 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Methionine and derivatives / Proline and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Pyrrolidinecarboxamides / N-acylpyrrolidines / 1-hydroxy-2-unsubstituted benzenoids / Fatty amides / Tertiary carboxylic acid amides
show 11 more
Substituents
Alpha-oligopeptide / Methionine or derivatives / N-acyl-alpha amino acid or derivatives / Proline or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Amphetamine or derivatives / Pyrrolidine-2-carboxamide / N-acylpyrrolidine
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not 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. ...
Gene Name
lef
Uniprot ID
P15917
Uniprot Name
Lethal factor
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:50