NAV

1-Hexadecanosulfonyl-O-L-Serine

Identification

Generic Name
1-Hexadecanosulfonyl-O-L-Serine
DrugBank Accession Number
DB03692
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 393.582
Monoisotopic: 393.254894053
Chemical Formula
C19H39NO5S
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
UPhospholipase A1Not AvailableEscherichia coli (strain K12)
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 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 / Sulfonyls / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 1 more
Substituents
Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NKAIXQDVYXAWPS-SFHVURJKSA-N
InChI
InChI=1S/C19H39NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-26(23,24)25-17-18(20)19(21)22/h18H,2-17,20H2,1H3,(H,21,22)/t18-/m0/s1
IUPAC Name
(2S)-2-amino-3-[(hexadecane-1-sulfonyl)oxy]propanoic acid
SMILES
[H][C@](N)(COS(=O)(=O)CCCCCCCCCCCCCCCC)C(O)=O

References

General References
Not Available
PubChem Compound
17754154
PubChem Substance
46508679
ChemSpider
16744187
ZINC
ZINC000014880865
PDBe Ligand
S1H
PDB Entries
1fw3

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 Solubility0.000448 mg/mLALOGPS
logP2.21ALOGPS
logP2.86Chemaxon
logS-5.9ALOGPS
pKa (Strongest Acidic)1.54Chemaxon
pKa (Strongest Basic)8.57Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area106.69 Å2Chemaxon
Rotatable Bond Count19Chemaxon
Refractivity104 m3·mol-1Chemaxon
Polarizability47.23 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9194
Blood Brain Barrier+0.7214
Caco-2 permeable-0.6259
P-glycoprotein substrateNon-substrate0.5501
P-glycoprotein inhibitor INon-inhibitor0.7941
P-glycoprotein inhibitor IINon-inhibitor0.9943
Renal organic cation transporterNon-inhibitor0.9353
CYP450 2C9 substrateNon-substrate0.8934
CYP450 2D6 substrateNon-substrate0.8122
CYP450 3A4 substrateNon-substrate0.6429
CYP450 1A2 substrateNon-inhibitor0.7313
CYP450 2C9 inhibitorNon-inhibitor0.8167
CYP450 2D6 inhibitorNon-inhibitor0.8845
CYP450 2C19 inhibitorNon-inhibitor0.7609
CYP450 3A4 inhibitorNon-inhibitor0.9269
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9832
Ames testNon AMES toxic0.7086
CarcinogenicityNon-carcinogens0.6197
BiodegradationReady biodegradable0.7161
Rat acute toxicity2.2047 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8858
hERG inhibition (predictor II)Non-inhibitor0.8622
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-MSsplash10-006w-9664000000-1289b4bf887ee4451b42
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-3079000000-d6a94ccdf3da32a0d5df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-0009000000-b0b1e68365b89c671445
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-2019000000-47893968d1e2ea7f7bf8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-2924000000-2e3cee5787e4795f59cb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9326000000-20d743cddfcf54b703c2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052g-9200000000-3d8929866cab5cdf37bc
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]-187.50652
predicted
DeepCCS 1.0 (2019)
[M+H]+189.86452
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.95767
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Phospholipase A1
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membra...
Gene Name
pldA
Uniprot ID
P0A921
Uniprot Name
Phospholipase A1
Molecular Weight
33162.93 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