[2(R,S)-2-Sulfanylheptanoyl]-Phe-Ala

Identification

Name
[2(R,S)-2-Sulfanylheptanoyl]-Phe-Ala
Accession Number
DB02597  (EXPT03060)
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: 380.502
Monoisotopic: 380.176978084
Chemical Formula
C19H28N2O4S
InChI Key
GOIYKVXXGCPHQU-BPUTZDHNSA-N
InChI
InChI=1S/C19H28N2O4S/c1-3-4-6-11-16(26)18(23)21-15(12-14-9-7-5-8-10-14)17(22)20-13(2)19(24)25/h5,7-10,13,15-16,26H,3-4,6,11-12H2,1-2H3,(H,20,22)(H,21,23)(H,24,25)/t13-,15-,16-/m0/s1
IUPAC Name
(2S)-2-[(2S)-3-phenyl-2-[(2S)-2-sulfanylheptanamido]propanamido]propanoic acid
SMILES
[H][[email protected]@](C)(NC(=O)[[email protected]]([H])(CC1=CC=CC=C1)NC(=O)[[email protected]@]([H])(S)CCCCC)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThermolysinNot AvailableGeobacillus stearothermophilus
UNeprilysinNot AvailableHuman
UThermolysinNot AvailableBacillus thermoproteolyticus
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
5289469
PubChem Substance
46505753
ChemSpider
4451431
Therapeutic Targets Database
DNC001441
HET
TI1
PDB Entries
1qf1 / 1r1i

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 Solubility0.0104 mg/mLALOGPS
logP3.23ALOGPS
logP3.01ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.83ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area95.5 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity102.51 m3·mol-1ChemAxon
Polarizability41.19 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8077
Blood Brain Barrier+0.6623
Caco-2 permeable-0.7367
P-glycoprotein substrateSubstrate0.7047
P-glycoprotein inhibitor INon-inhibitor0.9495
P-glycoprotein inhibitor IINon-inhibitor0.9804
Renal organic cation transporterNon-inhibitor0.965
CYP450 2C9 substrateNon-substrate0.7541
CYP450 2D6 substrateNon-substrate0.8426
CYP450 3A4 substrateNon-substrate0.6599
CYP450 1A2 substrateNon-inhibitor0.8707
CYP450 2C9 inhibitorNon-inhibitor0.7998
CYP450 2D6 inhibitorNon-inhibitor0.9042
CYP450 2C19 inhibitorNon-inhibitor0.7294
CYP450 3A4 inhibitorNon-inhibitor0.6956
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9106
Ames testNon AMES toxic0.9199
CarcinogenicityNon-carcinogens0.9239
BiodegradationNot ready biodegradable0.8614
Rat acute toxicity2.1308 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9963
hERG inhibition (predictor II)Non-inhibitor0.9411
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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Phenylalanine and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Alanine and derivatives / Amphetamines and derivatives / N-acyl amines / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Alkylthiols
show 5 more
Substituents
Alpha-dipeptide / Phenylalanine or derivatives / N-acyl-alpha-amino acid / N-acyl-l-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alanine or derivatives / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Amphetamine or derivatives
show 20 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Metalloendopeptidase activity
Specific Function
Extracellular zinc metalloprotease.
Gene Name
nprS
Uniprot ID
P43133
Uniprot Name
Thermolysin
Molecular Weight
60616.22 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Thermolysin-like specificity, but is almost confined on acting on polypeptides of up to 30 amino acids (PubMed:15283675, PubMed:8168535). Biologically important in the destruction of opioid peptide...
Gene Name
MME
Uniprot ID
P08473
Uniprot Name
Neprilysin
Molecular Weight
85513.225 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]
Kind
Protein
Organism
Bacillus thermoproteolyticus
Pharmacological action
Unknown
General Function
Metalloendopeptidase activity
Specific Function
Extracellular zinc metalloprotease.
Gene Name
npr
Uniprot ID
P00800
Uniprot Name
Thermolysin
Molecular Weight
60103.515 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:00