Palmitoleic Acid
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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
Target Actions Organism UUDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase Not Available Aquifex aeolicus (strain VF5) UFatty-acid peroxygenase Not Available Bacillus subtilis (strain 168) UBifunctional cytochrome P450/NADPH--P450 reductase Not Available Bacillus 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
- External Links
- 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
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) -0.1 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.000447 mg/mL ALOGPS logP 6.71 ALOGPS logP 5.89 Chemaxon logS -5.8 ALOGPS pKa (Strongest Acidic) 4.99 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 78.2 m3·mol-1 Chemaxon Polarizability 32.87 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9945 Blood Brain Barrier + 0.9539 Caco-2 permeable + 0.8371 P-glycoprotein substrate Non-substrate 0.5962 P-glycoprotein inhibitor I Non-inhibitor 0.9487 P-glycoprotein inhibitor II Non-inhibitor 0.8964 Renal organic cation transporter Non-inhibitor 0.9272 CYP450 2C9 substrate Non-substrate 0.7643 CYP450 2D6 substrate Non-substrate 0.8954 CYP450 3A4 substrate Non-substrate 0.6678 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.8972 CYP450 2D6 inhibitor Non-inhibitor 0.9545 CYP450 2C19 inhibitor Non-inhibitor 0.9467 CYP450 3A4 inhibitor Non-inhibitor 0.9295 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9349 Ames test Non AMES toxic 0.9674 Carcinogenicity Non-carcinogens 0.6568 Biodegradation Ready biodegradable 0.811 Rat acute toxicity 1.3991 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9133 hERG inhibition (predictor II) Non-inhibitor 0.9103
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 193.3792518 predictedDarkChem Lite v0.1.0 [M-H]- 193.9338518 predictedDarkChem Lite v0.1.0 [M-H]- 193.6257518 predictedDarkChem Lite v0.1.0 [M-H]- 193.3839518 predictedDarkChem Lite v0.1.0 [M-H]- 170.41113 predictedDeepCCS 1.0 (2019) [M+H]+ 174.4308 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.44191 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Aquifex aeolicus (strain VF5)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the hydrolysis of UDP-3-O-myristoyl-N-acetylglucosamine to form UDP-3-O-myristoylglucosamine and acetate, the committed step in lipid A biosynthesis.
- Specific Function
- metal ion binding
- Gene Name
- lpxC
- Uniprot ID
- O67648
- Uniprot Name
- UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase
- Molecular Weight
- 32144.765 Da
References
2. DetailsFatty-acid peroxygenase
- Kind
- Protein
- Organism
- Bacillus subtilis (strain 168)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the alpha- and beta-hydroxylation of myristic acid in the presence of hydrogen peroxide.
- Specific Function
- heme binding
- Gene Name
- cypC
- Uniprot ID
- O31440
- Uniprot Name
- Fatty-acid peroxygenase
- Molecular Weight
- 48108.7 Da
References
- Kind
- Protein
- Organism
- Bacillus megaterium
- Pharmacological action
- Unknown
- General Function
- Functions as a fatty acid monooxygenase (PubMed:11695892, PubMed:14653735, PubMed:16403573, PubMed:16566047, PubMed:17077084, PubMed:1727637, PubMed:17868686, PubMed:18004886, PubMed:18298086, PubMed:18619466, PubMed:18721129, PubMed:19492389, PubMed:20180779, PubMed:21110374, PubMed:21875028, PubMed:3106359, PubMed:7578081). Catalyzes hydroxylation of fatty acids at omega-1, omega-2 and omega-3 positions (PubMed:1727637, PubMed:21875028). Shows activity toward medium and long-chain fatty acids, with optimum chain lengths of 12, 14 and 16 carbons (lauric, myristic, and palmitic acids). Able to metabolize some of these primary metabolites to secondary and tertiary products (PubMed:1727637). Marginal activity towards short chain lengths of 8-10 carbons (PubMed:1727637, PubMed:18619466). Hydroxylates highly branched fatty acids, which play an essential role in membrane fluidity regulation (PubMed:16566047). Also displays a NADPH-dependent reductase activity in the C-terminal domain, which allows electron transfer from NADPH to the heme iron of the cytochrome P450 N-terminal domain (PubMed:11695892, PubMed:14653735, PubMed:16403573, PubMed:16566047, PubMed:17077084, PubMed:1727637, PubMed:17868686, PubMed:18004886, PubMed:18298086, PubMed:18619466, PubMed:18721129, PubMed:19492389, PubMed:20180779, PubMed:21110374, PubMed:21875028, PubMed:3106359, PubMed:7578081). Involved in inactivation of quorum sensing signals of other competing bacteria by oxidazing efficiently acyl homoserine lactones (AHLs), molecules involved in quorum sensing signaling pathways, and their lactonolysis products acyl homoserines (AHs) (PubMed:18020460).
- Specific Function
- aromatase activity
- Gene Name
- cyp102A1
- Uniprot ID
- P14779
- Uniprot Name
- Bifunctional cytochrome P450/NADPH--P450 reductase
- Molecular Weight
- 117780.49 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52