PALMITIC ACID
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
Mainterm | PALMITIC ACID |
Doc Type | ASP |
CAS Reg.No.(or other ID) | 57-10-3 |
Regnum |
173.340 172.210 172.860 |
From www.fda.gov
Computed Descriptors
Download SDF2D Structure | |
CID | 985 |
IUPAC Name | hexadecanoic acid |
InChI | InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) |
InChI Key | IPCSVZSSVZVIGE-UHFFFAOYSA-N |
Canonical SMILES | CCCCCCCCCCCCCCCC(=O)O |
Molecular Formula | C16H32O2 |
Wikipedia | calcium palmitate |
From Pubchem
Computed Properties
Property Name | Property Value |
---|---|
Molecular Weight | 256.43 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 14 |
Complexity | 178.0 |
CACTVS Substructure Key Fingerprint | A A A D c f B 4 M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A C A C A g A A C C A A A A g A I A A C Q C A A A A A A A A A A A A A E A A A A A A B I A A A A A Q A A E A A A A A A G I y K C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
Topological Polar Surface Area | 37.3 |
Monoisotopic Mass | 256.24 |
Exact Mass | 256.24 |
Compound Is Canonicalized | True |
Formal Charge | 0 |
Heavy Atom Count | 18 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9488 |
Human Intestinal Absorption | HIA+ | 0.9888 |
Caco-2 Permeability | Caco2+ | 0.8326 |
P-glycoprotein Substrate | Non-substrate | 0.6321 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9598 |
Non-inhibitor | 0.9277 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9266 |
Distribution | ||
Subcellular localization | Mitochondria | 0.5152 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7886 |
CYP450 2D6 Substrate | Non-substrate | 0.8956 |
CYP450 3A4 Substrate | Non-substrate | 0.6982 |
CYP450 1A2 Inhibitor | Inhibitor | 0.8326 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.8808 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9554 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9578 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9484 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9647 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9322 |
Non-inhibitor | 0.8868 | |
AMES Toxicity | Non AMES toxic | 0.9865 |
Carcinogens | Non-carcinogens | 0.6452 |
Fish Toxicity | High FHMT | 0.9144 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9990 |
Honey Bee Toxicity | High HBT | 0.6691 |
Biodegradation | Ready biodegradable | 0.8795 |
Acute Oral Toxicity | IV | 0.6378 |
Carcinogenicity (Three-class) | Non-required | 0.7057 |
From admetSAR
ADMET Predicted Profile --- Regression
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.5022 | LogS |
Caco-2 Permeability | 1.3950 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.3275 | LD50, mol/kg |
Fish Toxicity | 1.8920 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.3852 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
Route of Exposure | |
---|---|
Mechanism of Toxicity | |
Metabolism | |
Toxicity Values | |
Lethal Dose | |
Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
Minimum Risk Level | |
Health Effects | |
Treatment | |
Reference |
|
From T3DB
Taxonomic Classification
Kingdom | Organic compounds |
---|---|
Superclass | Lipids and lipid-like molecules |
Class | Fatty Acyls |
Subclass | Fatty acids and conjugates |
Intermediate Tree Nodes | Not available |
Direct Parent | Long-chain fatty acids |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | Long-chain fatty acid - Straight chain fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound |
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. |
From ClassyFire
Targets
- General Function:
- Small molecule binding
- Specific Function:
- This protein is, quantitatively, the main protein synthesized and secreted in the endometrium from mid-luteal phase of the menstrual cycle and during the first semester of pregnancy.
- Gene Name:
- PAEP
- Uniprot ID:
- P09466
- Molecular Weight:
- 20624.015 Da
References
- 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. [10592235 ]
- General Function:
- Palmitoyl-coa hydrolase activity
- Specific Function:
- Removes thioester-linked fatty acyl groups such as palmitate from modified cysteine residues in proteins or peptides during lysosomal degradation. Prefers acyl chain lengths of 14 to 18 carbons.
- Gene Name:
- PPT1
- Uniprot ID:
- P50897
- Molecular Weight:
- 34193.245 Da
References
- 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. [10592235 ]
- General Function:
- Photoreceptor activity
- Specific Function:
- Photoreceptor required for image-forming vision at low light intensity. Required for photoreceptor cell viability after birth. Light-induced isomerization of 11-cis to all-trans retinal triggers a conformational change leading to G-protein activation and release of all-trans retinal.
- Gene Name:
- RHO
- Uniprot ID:
- P08100
- Molecular Weight:
- 38892.335 Da
References
- 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. [10592235 ]
- General Function:
- Vitamin e binding
- Specific Function:
- Carrier protein. Binds to some hydrophobic molecules and promotes their transfer between the different cellular sites. Binds with high affinity to alpha-tocopherol. Also binds with a weaker affinity to other tocopherols and to tocotrienols. May have a transcriptional activatory activity via its association with alpha-tocopherol. Probably recognizes and binds some squalene structure, suggesting that it may regulate cholesterol biosynthesis by increasing the transfer of squalene to a metabolic active pool in the cell.
- Gene Name:
- SEC14L2
- Uniprot ID:
- O76054
- Molecular Weight:
- 46144.9 Da
References
- 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. [17016423 ]
- General Function:
- Lactose synthase activity
- Specific Function:
- Regulatory subunit of lactose synthase, changes the substrate specificity of galactosyltransferase in the mammary gland making glucose a good acceptor substrate for this enzyme. This enables LS to synthesize lactose, the major carbohydrate component of milk. In other tissues, galactosyltransferase transfers galactose onto the N-acetylglucosamine of the oligosaccharide chains in glycoproteins.
- Gene Name:
- LALBA
- Uniprot ID:
- P00709
- Molecular Weight:
- 16224.695 Da
References
- Barbana C, Perez MD, Pocovi C, Sanchez L, Wehbi Z: Interaction of human alpha-lactalbumin with fatty acids: determination of binding parameters. Biochemistry (Mosc). 2008 Jun;73(6):711-6. [18620538 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
- Gene Name:
- CYP2C8
- Uniprot ID:
- P10632
- Molecular Weight:
- 55824.275 Da
References
- Schoch GA, Yano JK, Wester MR, Griffin KJ, Stout CD, Johnson EF: Structure of human microsomal cytochrome P450 2C8. Evidence for a peripheral fatty acid binding site. J Biol Chem. 2004 Mar 5;279(10):9497-503. Epub 2003 Dec 15. [14676196 ]
- General Function:
- Transporter activity
- Specific Function:
- Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity).
- Gene Name:
- FABP4
- Uniprot ID:
- P15090
- Molecular Weight:
- 14718.815 Da
- General Function:
- Transporter activity
- Specific Function:
- High specificity for fatty acids. Highest affinity for C18 chain length. Decreasing the chain length or introducing double bonds reduces the affinity. May be involved in keratinocyte differentiation.
- Gene Name:
- FABP5
- Uniprot ID:
- Q01469
- Molecular Weight:
- 15164.36 Da
- General Function:
- Oleic acid binding
- Specific Function:
- FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters.
- Gene Name:
- FABP3
- Uniprot ID:
- P05413
- Molecular Weight:
- 14857.93 Da
- General Function:
- Transporter activity
- Specific Function:
- FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds saturated long-chain fatty acids with a high affinity, but binds with a lower affinity to unsaturated long-chain fatty acids. FABP2 may also help maintain energy homeostasis by functioning as a lipid sensor.
- Gene Name:
- FABP2
- Uniprot ID:
- P12104
- Molecular Weight:
- 15207.165 Da
- General Function:
- Zinc ion binding
- Specific Function:
- Transcription factor. Has a lower transcription activation potential than HNF4-alpha.
- Gene Name:
- HNF4G
- Uniprot ID:
- Q14541
- Molecular Weight:
- 45876.235 Da
- General Function:
- Triacyl lipopeptide binding
- Specific Function:
- Cooperates with LY96 to mediate the innate immune response to bacterial lipoproteins and other microbial cell wall components. Cooperates with TLR1 or TLR6 to mediate the innate immune response to bacterial lipoproteins or lipopeptides (PubMed:17889651). Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response. May also promote apoptosis in response to lipoproteins (PubMed:10426996). Recognizes mycoplasmal macrophage-activating lipopeptide-2kD (MALP-2), soluble tuberculosis factor (STF), phenol-soluble modulin (PSM) and B.burgdorferi outer surface protein A lipoprotein (OspA-L) cooperatively with TLR6 (PubMed:11441107). Acts as a receptor for M.tuberculosis lipoproteins LprA, LprG, LpqH and PhoS1 (pstS1), some lipoproteins are dependent on other coreceptors (TLR1, CD14 and/or CD36).The lipoproteins act as agonists to modulate antigen presenting cell functions in response to the pathogen (PubMed:19362712). Forms activation clusters composed of several receptors depending on the ligand, these clusters trigger signaling from the cell surface and subsequently are targeted to the Golgi in a lipid-raft dependent pathway. Forms the cluster TLR2:TLR6:CD14:CD36 in response to diacylated lipopeptides and TLR2:TLR1:CD14 in response to triacylated lipopeptides (PubMed:16880211).
- Gene Name:
- TLR2
- Uniprot ID:
- O60603
- Molecular Weight:
- 89836.575 Da
- Specific Function:
- May play a role in vesicular transport from endoplasmic reticulum to Golgi.
- Gene Name:
- TRAPPC3
- Uniprot ID:
- O43617
- Molecular Weight:
- 20273.915 Da
- General Function:
- Transporter activity
- Specific Function:
- May play a role in lipid transport protein in Schwann cells. May bind cholesterol.
- Gene Name:
- PMP2
- Uniprot ID:
- P02689
- Molecular Weight:
- 14909.305 Da
References
- 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. [10592235 ]
- Specific Function:
- Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
- Gene Name:
- FBF1
- Uniprot ID:
- Q8TES7
- Molecular Weight:
- 125445.19 Da
References
- Krishnakumar SS, Panda D: Spatial relationship between the prodan site, Trp-214, and Cys-34 residues in human serum albumin and loss of structure through incremental unfolding. Biochemistry. 2002 Jun 11;41(23):7443-52. [12044178 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
- Gene Name:
- PPARA
- Uniprot ID:
- Q07869
- Molecular Weight:
- 52224.595 Da
References
- Murakami K, Ide T, Suzuki M, Mochizuki T, Kadowaki T: Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. Biochem Biophys Res Commun. 1999 Jul 14;260(3):609-13. [10403814 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand.
- Gene Name:
- PPARD
- Uniprot ID:
- Q03181
- Molecular Weight:
- 49902.99 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRA
- Uniprot ID:
- P11474
- Molecular Weight:
- 45509.11 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Lipid binding
- Uniprot ID:
- P83812
- Molecular Weight:
- 32173.81 Da
- General Function:
- Lipid binding
- Specific Function:
- Binds long-chain fatty acids, such as palmitate, and may play a role in lipid transport or fatty acid metabolism.
- Uniprot ID:
- Q9X1H9
- Molecular Weight:
- 32574.335 Da
From T3DB