Palmitoleic Acid

Identification

Name
Palmitoleic Acid
Accession Number
DB04257  (EXPT02495)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (9Z)-hexadecenoic acid
  • (Z)-9-hexadecenoic acid
  • (Z)-hexadec-9-enoic acid
  • 9-cis-hexadecenoic acid
  • cis-9-Hexadecenoic acid
  • palmitolinoleic acid
  • zoomaric acid
External IDs
16:1(N-7)
Categories
UNII
209B6YPZ4I
CAS number
373-49-9
Weight
Average: 254.4082
Monoisotopic: 254.224580204
Chemical Formula
C16H30O2
InChI Key
SECPZKHBENQXJG-FPLPWBNLSA-N
InChI
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-
IUPAC Name
(9Z)-hexadec-9-enoic acid
SMILES
CCCCCC\C=C/CCCCCCCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFatty-acid peroxygenaseNot AvailableBacillus subtilis (strain 168)
UBifunctional P-450/NADPH-P450 reductaseNot AvailableBacillus megaterium
UUDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylaseNot AvailableAquifex aeolicus (strain VF5)
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
PathwayCategory
Fatty Acid MetabolismMetabolic
Inner Membrane TransportMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0003229
KEGG Compound
C08362
PubChem Compound
445638
PubChem Substance
46508831
ChemSpider
393216
BindingDB
50269531
ChEBI
28716
ChEMBL
CHEMBL453509
HET
PAM
PDB Entries
1fag / 1fk3 / 1izo / 1smj / 1uvb / 1yh8 / 1yhc / 2uuh / 3ekd / 3gbg
show 17 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
PropertyValueSource
melting point (°C)-0.1 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.000447 mg/mLALOGPS
logP6.71ALOGPS
logP5.89ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m3·mol-1ChemAxon
Polarizability32.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9945
Blood Brain Barrier+0.9539
Caco-2 permeable+0.8371
P-glycoprotein substrateNon-substrate0.5962
P-glycoprotein inhibitor INon-inhibitor0.9487
P-glycoprotein inhibitor IINon-inhibitor0.8964
Renal organic cation transporterNon-inhibitor0.9272
CYP450 2C9 substrateNon-substrate0.7643
CYP450 2D6 substrateNon-substrate0.8954
CYP450 3A4 substrateNon-substrate0.6678
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.8972
CYP450 2D6 inhibitorNon-inhibitor0.9545
CYP450 2C19 inhibitorNon-inhibitor0.9467
CYP450 3A4 inhibitorNon-inhibitor0.9295
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9349
Ames testNon AMES toxic0.9674
CarcinogenicityNon-carcinogens0.6568
BiodegradationReady biodegradable0.811
Rat acute toxicity1.3991 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9133
hERG inhibition (predictor II)Non-inhibitor0.9103
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
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-00nb-5900000000-90ab9a21246ad658bda0
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00mk-2900000000-6683cd8579813b4f1ebb
GC-MS Spectrum - GC-MSGC-MSsplash10-00nb-5900000000-90ab9a21246ad658bda0
GC-MS Spectrum - GC-MSGC-MSsplash10-00nb-5900000000-90ab9a21246ad658bda0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0090000000-202819132f83589a248b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4s-7790000000-ff129e0c7cc2a7e4cf19
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9600000000-749f09fec19d95c21683
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-5005f244d7d1c3502c3e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zg0-1090000000-cac7fce9a75b0f1abd63
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9320000000-2e782c63ccf72afe9be9
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0090000000-35027c88ff732ff74b4c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0090000000-3cac469ac1efde0a3543
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0090000000-e5833c7aa4795570bdc4
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-9090000000-909ebad9120d01bf8e79
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004j-9000000000-fb5a2e21c48a7d72aac8
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0udi-0090000000-09c91b61deabc72625f3
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0udi-0090000000-993c95f96e1ca69a41c0
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0udi-0090000000-e72ac58f23bacbf37344
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Unsaturated fatty acids / Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Long-chain fatty acid / Unsaturated fatty acid / Straight chain fatty acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
hexadec-9-enoic acid (CHEBI:28716) / Unsaturated fatty acids, Monounsaturated fatty acids (C08362) / Unsaturated fatty acids (LMFA01030056)

Targets

Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific Function
Catalyzes the alpha- and beta-hydroxylation of myristic acid in the presence of hydrogen peroxide.
Gene Name
cypC
Uniprot ID
O31440
Uniprot Name
Fatty-acid peroxygenase
Molecular Weight
48108.7 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 megaterium
Pharmacological action
Unknown
General Function
Nadph-hemoprotein reductase activity
Specific Function
Functions as a fatty acid monooxygenase. Catalyzes hydroxylation of medium and long-chain fatty acids at omega-1, omega-2 and omega-3 positions, with optimum chain lengths of 12-16 carbons (lauric,...
Gene Name
cyp102A1
Uniprot ID
P14779
Uniprot Name
Bifunctional cytochrome P450/NADPH--P450 reductase
Molecular Weight
117780.49 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
Aquifex aeolicus (strain VF5)
Pharmacological action
Unknown
General Function
Udp-3-o-[3-hydroxymyristoyl] n-acetylglucosamine deacetylase activity
Specific Function
Involved in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell.
Gene Name
lpxC
Uniprot ID
O67648
Uniprot Name
UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase
Molecular Weight
32144.765 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 November 02, 2018 05:54