O-Benzylsulfonyl-Serine

Identification

Name
O-Benzylsulfonyl-Serine
Accession Number
DB01973  (EXPT02878)
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: 259.279
Monoisotopic: 259.051443221
Chemical Formula
C10H13NO5S
InChI Key
GCZVEKLTOLTWLM-VIFPVBQESA-N
InChI
InChI=1S/C10H13NO5S/c11-9(10(12)13)6-16-17(14,15)7-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/m0/s1
IUPAC Name
(2S)-2-amino-3-(phenylmethanesulfonyloxy)propanoic acid
SMILES
N[[email protected]@H](COS(=O)(=O)CC1=CC=CC=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USubtilisin SavinaseNot AvailableBacillus lentus
UTrypsin-2Not AvailableHuman
UCarboxymethylenebutenolidaseNot AvailablePseudomonas sp. (strain B13)
UCapsid scaffolding proteinNot AvailableHHV-5
UAlkaline proteaseNot AvailableBacillus alcalophilus
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
17754162
PubChem Substance
46506745
ChemSpider
16744196
HET
SEB
PDB Entries
1c9m / 1c9n / 1ggv / 1iav / 1iec / 1pqa / 1q5p / 1ziy / 1zj4 / 1zj5
show 10 more

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 Solubility2.3 mg/mLALOGPS
logP-1.4ALOGPS
logP-2.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.53ChemAxon
pKa (Strongest Basic)8.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area106.69 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity59.53 m3·mol-1ChemAxon
Polarizability24.47 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8611
Blood Brain Barrier+0.7139
Caco-2 permeable-0.6345
P-glycoprotein substrateNon-substrate0.6666
P-glycoprotein inhibitor INon-inhibitor0.8716
P-glycoprotein inhibitor IINon-inhibitor0.9956
Renal organic cation transporterNon-inhibitor0.917
CYP450 2C9 substrateNon-substrate0.8984
CYP450 2D6 substrateNon-substrate0.8216
CYP450 3A4 substrateNon-substrate0.7048
CYP450 1A2 substrateNon-inhibitor0.7653
CYP450 2C9 inhibitorNon-inhibitor0.8474
CYP450 2D6 inhibitorNon-inhibitor0.9038
CYP450 2C19 inhibitorNon-inhibitor0.8276
CYP450 3A4 inhibitorNon-inhibitor0.9358
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9866
Ames testNon AMES toxic0.5848
CarcinogenicityNon-carcinogens0.5164
BiodegradationReady biodegradable0.5321
Rat acute toxicity2.0404 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.918
hERG inhibition (predictor II)Non-inhibitor0.9067
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Sulfonic acid esters / Organosulfonic acid esters / Benzene and substituted derivatives / Sulfonyls / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
Substituents
L-alpha-amino acid / Monocyclic benzene moiety / Sulfonic acid ester / Organosulfonic acid ester / Benzenoid / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Amino acid / Carboxylic acid
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Bacillus lentus
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Subtilisin is an extracellular alkaline serine protease, it catalyzes the hydrolysis of proteins and peptide amides.
Gene Name
Not Available
Uniprot ID
P29600
Uniprot Name
Subtilisin Savinase
Molecular Weight
26698.32 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
Serine-type endopeptidase activity
Specific Function
In the ileum, may be involved in defensin processing, including DEFA5.
Gene Name
PRSS2
Uniprot ID
P07478
Uniprot Name
Trypsin-2
Molecular Weight
26487.55 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
Pseudomonas sp. (strain B13)
Pharmacological action
Unknown
General Function
Carboxymethylenebutenolidase activity
Specific Function
Ring cleavage of cyclic ester dienelactone to produce maleylacetate.
Gene Name
clcD
Uniprot ID
P0A115
Uniprot Name
Carboxymethylenebutenolidase
Molecular Weight
25554.855 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
HHV-5
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Capsid scaffolding protein: Acts as a scaffold protein by binding major capsid protein VP5 in the cytoplasm, inducing the nuclear localization of both proteins. Multimerizes in the nucleus such as ...
Gene Name
UL80
Uniprot ID
P16753
Uniprot Name
Capsid scaffolding protein
Molecular Weight
73851.155 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
Bacillus alcalophilus
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P27693
Uniprot Name
Alkaline protease
Molecular Weight
38852.735 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:51