Palmitoleic Acid

Identification

Generic Name
Palmitoleic Acid
DrugBank Accession Number
DB04257
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 254.4082
Monoisotopic: 254.224580204
Chemical Formula
C16H30O2
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)

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylaseNot AvailableAquifex aeolicus (strain VF5)
UFatty-acid peroxygenaseNot AvailableBacillus subtilis (strain 168)
UBifunctional P-450/NADPH-P450 reductaseNot AvailableBacillus megaterium
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
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
Unsaturated fatty acids / Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Long-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / 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)
Affected organisms
Not Available

Chemical Identifiers

UNII
209B6YPZ4I
CAS number
373-49-9
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

References

General References
Not Available
Human Metabolome Database
HMDB0003229
KEGG Compound
C08362
PubChem Compound
445638
PubChem Substance
46508831
ChemSpider
393216
BindingDB
50269531
ChEBI
28716
ChEMBL
CHEMBL453509
ZINC
ZINC000008221009
PDBe Ligand
PAM
PDB Entries
1fag / 1fk3 / 1izo / 1smj / 1uvb / 1yh8 / 1yhc / 2uuh / 3ekd / 3gbg
show 43 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
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-MSsplash10-0006-8910000000-20fcd1fc2d9e095b2c24
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
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-004i-0092000000-b8aabbdc61f9b89ac359
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-004i-0092000000-b8aabbdc61f9b89ac359
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-004i-0092000000-b8aabbdc61f9b89ac359
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0udi-0090000000-993c95f96e1ca69a41c0
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0udi-0090000000-e72ac58f23bacbf37344
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0udi-0090000000-d1585cc46cbce84a0506
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0udi-0091000000-fd89101236e85a2d9154
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05o1-9530000000-949cbb714aa2eb149709
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-d76b1e618180205c4a4e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1190000000-dba4e57ba79ff9a07e8b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0159-9200000000-1a404dff954899f13b8c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05mx-9710000000-9dc24ef551b81de3bba2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-067l-9000000000-ce3e88ac364f71ae3906
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
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]-193.3792518
predicted
DarkChem Lite v0.1.0
[M-H]-193.9338518
predicted
DarkChem Lite v0.1.0
[M-H]-193.6257518
predicted
DarkChem Lite v0.1.0
[M-H]-193.3839518
predicted
DarkChem Lite v0.1.0
[M-H]-170.41113
predicted
DeepCCS 1.0 (2019)
[M+H]+174.4308
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.44191
predicted
DeepCCS 1.0 (2019)

Targets

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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. [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]
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. [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]
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. [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]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52