Identification
NamePalmitoleic Acid
Accession NumberDB04257  (EXPT02495)
TypeSmall Molecule
GroupsExperimental
DescriptionNot 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)
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII209B6YPZ4I
CAS number373-49-9
WeightAverage: 254.4082
Monoisotopic: 254.224580204
Chemical FormulaC16H30O2
InChI KeySECPZKHBENQXJG-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylaseProteinunknownNot AvailableAquifex aeolicus (strain VF5)O67648 details
Fatty-acid peroxygenaseProteinunknownNot AvailableBacillus subtilis (strain 168)O31440 details
Bifunctional cytochrome P450/NADPH--P450 reductaseProteinunknownNot AvailableBacillus megateriumP14779 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-90ab9a21246ad658bda0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00mk-2900000000-6683cd8579813b4f1ebbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-35027c88ff732ff74b4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-3cac469ac1efde0a3543View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-e5833c7aa4795570bdc4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-9090000000-909ebad9120d01bf8e79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-fb5a2e21c48a7d72aac8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0090000000-09c91b61deabc72625f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0090000000-993c95f96e1ca69a41c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0090000000-993c95f96e1ca69a41c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0090000000-e72ac58f23bacbf37344View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0090000000-e72ac58f23bacbf37344View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0090000000-202819132f83589a248bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-7790000000-ff129e0c7cc2a7e4cf19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-749f09fec19d95c21683View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-5005f244d7d1c3502c3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1090000000-cac7fce9a75b0f1abd63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2e782c63ccf72afe9be9View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acids
Alternative ParentsUnsaturated fatty acids / Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsLong-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 FrameworkAliphatic acyclic compounds
External Descriptorshexadec-9-enoic acid (CHEBI:28716 ) / Unsaturated fatty acids, Monounsaturated fatty acids (C08362 ) / Unsaturated fatty acids (LMFA01030056 )

Targets

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
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 ]
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
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, myristic, and palmitic acids). The reductase domain is required for electron transfer from NADP to cytochrome P450.
Gene Name:
cyp102A1
Uniprot ID:
P14779
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 ]
Drug created on June 13, 2005 07:24 / Updated on June 24, 2017 13:22