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Lysophosphotidylserine

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Overview

Structure
DrugBank ID
DB04136
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
Lysophosphotidylserine
DrugBank Accession Number
DB04136
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 485.5491
Monoisotopic: 485.275368523
Chemical Formula
C21H44NO9P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProthrombinNot 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
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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 glycerophosphoserines. These are lipids containing a glycerol moiety carrying a phosphoserine at the 3-position.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Glycerophospholipids
Sub Class
Glycerophosphoserines
Direct Parent
Glycerophosphoserines
Alternative Parents
L-alpha-amino acids / Phosphoethanolamines / Dialkyl phosphates / Secondary alcohols / Hemiacetals / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides
show 3 more
Substituents
Alcohol / Aliphatic acyclic compound / Alkyl phosphate / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Carbonyl group / Carboxylic acid
show 19 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
RPZLJDFLPRHXGM-HSALFYBXSA-N
InChI
InChI=1S/C21H44NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-20(24)29-15-18(23)16-30-32(27,28)31-17-19(22)21(25)26/h18-20,23-24H,2-17,22H2,1H3,(H,25,26)(H,27,28)/t18-,19+,20-/m1/s1
IUPAC Name
(2S)-2-amino-3-({hydroxy[(2R)-2-hydroxy-3-{[(1R)-1-hydroxypentadecyl]oxy}propoxy]phosphoryl}oxy)propanoic acid
SMILES
[H][C@@](O)(CO[C@@]([H])(O)CCCCCCCCCCCCCC)COP(O)(=O)OC[C@]([H])(N)C(O)=O

References

General References
Not Available
PubChem Compound
17754066
PubChem Substance
46505939
ChemSpider
16744091
ChEMBL
CHEMBL1234081
ZINC
ZINC000038377594
PDBe Ligand
LPS
PDB Entries
1nl2 / 8kh5

Clinical Trials

Clinical Trials
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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 Solubility0.00707 mg/mLALOGPS
logP0.47ALOGPS
logP1.96Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.51Chemaxon
pKa (Strongest Basic)9.38Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area168.77 Å2Chemaxon
Rotatable Bond Count23Chemaxon
Refractivity120.03 m3·mol-1Chemaxon
Polarizability53.69 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7152
Blood Brain Barrier+0.6126
Caco-2 permeable-0.6716
P-glycoprotein substrateSubstrate0.5678
P-glycoprotein inhibitor INon-inhibitor0.7851
P-glycoprotein inhibitor IINon-inhibitor0.9767
Renal organic cation transporterNon-inhibitor0.9306
CYP450 2C9 substrateNon-substrate0.8819
CYP450 2D6 substrateNon-substrate0.8018
CYP450 3A4 substrateNon-substrate0.6137
CYP450 1A2 substrateNon-inhibitor0.6519
CYP450 2C9 inhibitorNon-inhibitor0.8646
CYP450 2D6 inhibitorNon-inhibitor0.8616
CYP450 2C19 inhibitorNon-inhibitor0.7438
CYP450 3A4 inhibitorNon-inhibitor0.7825
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9657
Ames testNon AMES toxic0.7416
CarcinogenicityNon-carcinogens0.8202
BiodegradationNot ready biodegradable0.6789
Rat acute toxicity2.0135 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9293
hERG inhibition (predictor II)Non-inhibitor0.7637
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/MSsplash10-014r-3103900000-23b9e7b95f245cc0a4be
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-1109000000-0786da692f6ac3fc9bd2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002g-3592100000-831e62e7ff60c8b07421
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-39a3999a98e9dff2a495
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9401000000-7d9bc5c67f27b06fe8ca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-9181000000-23d9ef642bc76ea99999
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]-195.5211
predicted
DeepCCS 1.0 (2019)
[M+H]+198.8296
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.39491
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Prothrombin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing. Thrombin triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2 and IL8/CXCL8, in endothelial cells (PubMed:30568593, PubMed:9780208)
Specific Function
calcium ion binding
Gene Name
F2
Uniprot ID
P00734
Uniprot Name
Prothrombin
Molecular Weight
70036.295 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