NAV

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

Identification

Generic Name
[2(R,S)-2-Sulfanylheptanoyl]-Phe-Ala
DrugBank Accession Number
DB02597
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 380.502
Monoisotopic: 380.176978084
Chemical Formula
C19H28N2O4S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThermolysinNot AvailableBacillus thermoproteolyticus
UThermolysinNot AvailableGeobacillus stearothermophilus
UNeprilysinNot AvailableHumans
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 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
Alanine or derivatives / Alkylthiol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group
show 20 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@@](C)(NC(=O)[C@]([H])(CC1=CC=CC=C1)NC(=O)[C@@]([H])(S)CCCCC)C(O)=O

References

General References
Not Available
PubChem Compound
5289469
PubChem Substance
46505753
ChemSpider
4451431
ZINC
ZINC000006352218
Therapeutic Targets Database
DNC001441
PDBe Ligand
TI1
PDB Entries
1qf1 / 1r1i

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 Solubility0.0104 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/MSsplash10-0006-0192000000-cf27d00ed2b245e58221
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-2039000000-017f2c90c23a3ddc349d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01c1-3931000000-c529811e1012c64ed5af
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000b-4893000000-027609b07fa4c75b5dfa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9810000000-299cc373e3ef57521192
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-4920000000-04c95673ec462ebd6013
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]-195.23529
predicted
DeepCCS 1.0 (2019)
[M+H]+197.63084
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.7693
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thermolysin
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. [Article]
Details2. Thermolysin
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. [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]
Details3. Neprilysin
Kind
Protein
Organism
Humans
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. [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 August 01, 2020 13:44