(2E,4R,5S)-2,3,4,5-TETRAHYDROXY-6-(PALMITOYLOXY)HEX-2-ENOIC ACID

Identification

Generic Name
(2E,4R,5S)-2,3,4,5-TETRAHYDROXY-6-(PALMITOYLOXY)HEX-2-ENOIC ACID
DrugBank Accession Number
DB08438
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 432.5482
Monoisotopic: 432.272318256
Chemical Formula
C22H40O8
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHyaluronate lyaseNot AvailableStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
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 medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Hydroxy acids and derivatives
Sub Class
Medium-chain hydroxy acids and derivatives
Direct Parent
Medium-chain hydroxy acids and derivatives
Alternative Parents
Medium-chain fatty acids / Hydroxy fatty acids / Fatty acid esters / Unsaturated fatty acids / Dicarboxylic acids and derivatives / Vinylogous acids / Secondary alcohols / Enediols / Carboxylic acid esters / 1,2-diols
show 4 more
Substituents
1,2-diol / Alcohol / Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Enediol / Fatty acid ester
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
XWTWKBKNEMLBKW-KCWNHAIFSA-N
InChI
InChI=1S/C22H40O8/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)30-16-17(23)19(25)20(26)21(27)22(28)29/h17,19,23,25-27H,2-16H2,1H3,(H,28,29)/b21-20-/t17-,19+/m0/s1
IUPAC Name
(2Z,4R,5S)-6-(hexadecanoyloxy)-2,3,4,5-tetrahydroxyhex-2-enoic acid
SMILES
[H][C@](O)(COC(=O)CCCCCCCCCCCCCCC)[C@@]([H])(O)C(\O)=C(\O)C(O)=O

References

General References
Not Available
PubChem Compound
54736482
PubChem Substance
99444909
ChemSpider
26330358
ZINC
ZINC000100036745
PDBe Ligand
PVC
PDB Entries
1w3y

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 Solubility0.0118 mg/mLALOGPS
logP4.39ALOGPS
logP4.11Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)2.86Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area144.52 Å2Chemaxon
Rotatable Bond Count20Chemaxon
Refractivity114.12 m3·mol-1Chemaxon
Polarizability49.76 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.723
Blood Brain Barrier+0.6084
Caco-2 permeable-0.6474
P-glycoprotein substrateSubstrate0.6929
P-glycoprotein inhibitor INon-inhibitor0.8713
P-glycoprotein inhibitor IINon-inhibitor0.7894
Renal organic cation transporterNon-inhibitor0.9235
CYP450 2C9 substrateNon-substrate0.8641
CYP450 2D6 substrateNon-substrate0.8657
CYP450 3A4 substrateNon-substrate0.5481
CYP450 1A2 substrateNon-inhibitor0.6636
CYP450 2C9 inhibitorNon-inhibitor0.824
CYP450 2D6 inhibitorNon-inhibitor0.8558
CYP450 2C19 inhibitorNon-inhibitor0.8412
CYP450 3A4 inhibitorNon-inhibitor0.8135
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9183
Ames testNon AMES toxic0.8937
CarcinogenicityNon-carcinogens0.8743
BiodegradationReady biodegradable0.979
Rat acute toxicity1.3630 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9584
hERG inhibition (predictor II)Non-inhibitor0.693
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/MSsplash10-00m1-6952500000-9a5820b2b13697b24532
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-9525300000-c19330a2fe148891d25f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000j-4295100000-3f220405f83f1b96f9a1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9111000000-1b684fb772555def475c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-4090000000-7e651793d16d6db94167
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0532-9340000000-cef06fc9386df0fd6a80
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]-209.75189
predicted
DeepCCS 1.0 (2019)
[M+H]+213.20427
predicted
DeepCCS 1.0 (2019)
[M+Na]+221.16045
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
Hyaluronate lyase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q54873
Uniprot Name
Hyaluronate lyase
Molecular Weight
120770.645 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]

Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52