(R)-3-hydroxytetradecanoic acid

Identification

Generic Name
(R)-3-hydroxytetradecanoic acid
DrugBank Accession Number
DB02767
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 244.3703
Monoisotopic: 244.203844762
Chemical Formula
C14H28O3
Synonyms
  • (−)-3-hydroxymyristic acid
  • (3R)-hydroxymyristic acid
  • (R)-(-)-3-Hydroxytetradecanoic acid
  • (R)-(−)-3-hydroxytetradecanoic acid
  • (R)-3-Hydroxymyristic acid
  • (R)-3-Hydroxytetradecanoic acid
  • D-(-)-beta-Hydroxymyristic acid
  • D-(−)-β-hydroxymyristic acid
  • β-hydroxymyristic acid
  • β-hydroxytetradecanoic acid

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProtein TonBNot AvailableEscherichia coli (strain K12)
ULymphocyte antigen 96Not AvailableHumans
UToll-like receptor 4Not AvailableHumans
UFerrichrome-iron receptorNot 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
PathwayCategory
Fatty Acid BiosynthesisMetabolic
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 long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Long-chain fatty acids
Alternative Parents
Hydroxy fatty acids / Beta hydroxy acids and derivatives / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alcohol / Aliphatic acyclic compound / Beta-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Hydroxy acid / Hydroxy fatty acid / Long-chain fatty acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
(3R)-3-hydroxy fatty acid, 3-hydroxytetradecanoic acid (CHEBI:42539) / Hydroxy fatty acids (LMFA01050322)
Affected organisms
Not Available

Chemical Identifiers

UNII
R7C245Y68X
CAS number
28715-21-1
InChI Key
ATRNZOYKSNPPBF-CYBMUJFWSA-N
InChI
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1
IUPAC Name
(3R)-3-hydroxytetradecanoic acid
SMILES
CCCCCCCCCCC[C@@H](O)CC(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0010731
PubChem Compound
5288266
PubChem Substance
46505492
ChemSpider
4450466
ChEBI
42539
ChEMBL
CHEMBL1232858
ZINC
ZINC000002039069
PDBe Ligand
FTT
PDB Entries
1fi1 / 1qff / 1qfg / 1qjq / 1qkc / 2grx / 3fxi / 4cu4 / 4d65 / 4ihg
show 9 more

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 Solubility0.0299 mg/mLALOGPS
logP4.69ALOGPS
logP4.14Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.67Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area57.53 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity69.4 m3·mol-1Chemaxon
Polarizability30.86 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9763
Blood Brain Barrier+0.768
Caco-2 permeable+0.6421
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.9678
P-glycoprotein inhibitor IINon-inhibitor0.8318
Renal organic cation transporterNon-inhibitor0.9304
CYP450 2C9 substrateNon-substrate0.8199
CYP450 2D6 substrateNon-substrate0.8732
CYP450 3A4 substrateNon-substrate0.6643
CYP450 1A2 substrateInhibitor0.5446
CYP450 2C9 inhibitorNon-inhibitor0.8213
CYP450 2D6 inhibitorNon-inhibitor0.911
CYP450 2C19 inhibitorNon-inhibitor0.8965
CYP450 3A4 inhibitorNon-inhibitor0.8825
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9089
Ames testNon AMES toxic0.972
CarcinogenicityNon-carcinogens0.7301
BiodegradationReady biodegradable0.8944
Rat acute toxicity1.3109 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9467
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-MSsplash10-000f-9500000000-d3837d6527b09790d09e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000b-9750000000-abe6126c50ab53269268
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-5090000000-ebce9e79ab63e6c2d012
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9120000000-38c2e398b05b4ce127d7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9200000000-89f2959143132d423436
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-3f76f5bd87d79860a032
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-350cf7a07d1a837ae9d2
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]-181.4748366
predicted
DarkChem Lite v0.1.0
[M-H]-183.0456366
predicted
DarkChem Lite v0.1.0
[M-H]-154.94466
predicted
DeepCCS 1.0 (2019)
[M+H]+182.8428366
predicted
DarkChem Lite v0.1.0
[M+H]+184.1056366
predicted
DarkChem Lite v0.1.0
[M+H]+157.58028
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.4892366
predicted
DarkChem Lite v0.1.0
[M+Na]+182.3486366
predicted
DarkChem Lite v0.1.0
[M+Na]+165.46089
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Siderophore transmembrane transporter activity
Specific Function
Interacts with outer membrane receptor proteins that carry out high-affinity binding and energy dependent uptake into the periplasmic space of specific substrates such as cobalamin, and various iro...
Gene Name
tonB
Uniprot ID
P02929
Uniprot Name
Protein TonB
Molecular Weight
26094.07 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Lipopolysaccharide receptor activity
Specific Function
Binds bacterial lipopolysaccharide (LPS) (PubMed:17803912, PubMed:17569869). Cooperates with TLR4 in the innate immune response to bacterial lipopolysaccharide (LPS), and with TLR2 in the response ...
Gene Name
LY96
Uniprot ID
Q9Y6Y9
Uniprot Name
Lymphocyte antigen 96
Molecular Weight
18545.345 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane signaling receptor activity
Specific Function
Cooperates with LY96 and CD14 to mediate the innate immune response to bacterial lipopolysaccharide (LPS). Acts via MYD88, TIRAP and TRAF6, leading to NF-kappa-B activation, cytokine secretion and ...
Gene Name
TLR4
Uniprot ID
O00206
Uniprot Name
Toll-like receptor 4
Molecular Weight
95679.19 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Virion binding
Specific Function
This receptor binds the ferrichrome-iron ligand. It interacts with the TonB protein, which is responsible for energy coupling of the ferrichrome-promoted iron transport system. Acts as a receptor f...
Gene Name
fhuA
Uniprot ID
P06971
Uniprot Name
Ferrichrome-iron receptor
Molecular Weight
82181.75 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