NAV

N-(Sulfanylacetyl)Tyrosylprolylmethioninamide

Identification

Generic Name
N-(Sulfanylacetyl)Tyrosylprolylmethioninamide
DrugBank Accession Number
DB01883
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 482.617
Monoisotopic: 482.16576147
Chemical Formula
C21H30N4O5S2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

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 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
1-hydroxy-2-unsubstituted benzenoid / Alkylthiol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@@](CCSC)(NC(=O)[C@]1([H])CCCN1C(=O)[C@]([H])(CC1=CC=C(O)C=C1)NC(=O)CS)C(N)=O

References

General References
Not Available
PubChem Compound
5289343
PubChem Substance
46506367
ChemSpider
4451333
ZINC
ZINC000033821516
PDBe Ligand
SD2
PDB Entries
1pwq

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 Solubility0.0197 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/MSsplash10-053r-0011900000-91d11f5b63e0b490647e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0133900000-50dcde4b34d023b1d83b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-8629800000-255f1aa512ca9cb3a64f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bta-9265700000-160b09ab94732d7a2c89
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xu-9641000000-e4852dfa211193dca485
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9310100000-f7f5a40780028ba54ff9
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]-205.72054
predicted
DeepCCS 1.0 (2019)
[M+H]+207.68181
predicted
DeepCCS 1.0 (2019)
[M+Na]+213.59435
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Lethal factor
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52