Azelaic Acid
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Basic Info
| Common Name | Azelaic Acid(F05518) |
| 2D Structure | |
| Description | Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis. |
| FRCD ID | F05518 |
| CAS Number | 123-99-9 |
| PubChem CID | 2266 |
| Formula | C9H16O4 |
| IUPAC Name | nonanedioic acid |
| InChI Key | BDJRBEYXGGNYIS-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) |
| Canonical SMILES | C(CCCC(=O)O)CCCC(=O)O |
| Isomeric SMILES | C(CCCC(=O)O)CCCC(=O)O |
| Wikipedia | Azelaic Acid |
| Synonyms |
Anchoic acid
Heptanedicarboxylic acid
azelaic acid
NONANEDIOIC ACID
123-99-9
Finacea
Azelex
Lepargylic acid
Skinoren
1,7-Heptanedicarboxylic acid
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty acids and conjugates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Medium-chain fatty acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Medium-chain fatty acid - Dicarboxylic 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 medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 188.223 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 8 |
| Complexity | 147 |
| Monoisotopic Mass | 188.105 |
| Exact Mass | 188.105 |
| XLogP | 1.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7397 |
| Human Intestinal Absorption | HIA+ | 0.5731 |
| Caco-2 Permeability | Caco2- | 0.6412 |
| P-glycoprotein Substrate | Non-substrate | 0.6969 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9845 |
| Non-inhibitor | 0.9229 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9359 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8984 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8447 |
| CYP450 2D6 Substrate | Non-substrate | 0.9050 |
| CYP450 3A4 Substrate | Non-substrate | 0.7534 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9390 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9729 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9762 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9600 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9927 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9348 |
| Non-inhibitor | 0.9602 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.8382 |
| Fish Toxicity | High FHMT | 0.8783 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6559 |
| Honey Bee Toxicity | High HBT | 0.6229 |
| Biodegradation | Ready biodegradable | 0.8506 |
| Acute Oral Toxicity | IV | 0.6448 |
| Carcinogenicity (Three-class) | Non-required | 0.7514 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.8273 | LogS |
| Caco-2 Permeability | 0.3625 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.3577 | LD50, mol/kg |
| Fish Toxicity | 2.3886 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3850 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Characterization and biological activity of PVA hydrogel containingchitooligosaccharides conjugated with gallic acid. | Carbohydr Polym | 2018 Oct 15 | 30092991 |
| Dietary fibers influence the intestinal SCFAs and plasma metabolites profiling ingrowing pigs. | Food Funct | 2016 Nov 9 | 27754504 |
| New and Emerging Treatments for Rosacea. | Am J Clin Dermatol | 2015 Dec | 26396117 |
| Inflammatory acne management with a novel prescription dietary supplement. | J Drugs Dermatol | 2012 Dec | 23377512 |
| Acne vulgaris. | BMJ Clin Evid | 2011 Jan 5 | 21477388 |
| Alternative therapies for common dermatologic disorders, part 1. | Prim Care | 2010 Jun | 20493336 |
| A review of the diagnosis and treatment of rosacea. | Postgrad Med | 2010 Jan | 20107297 |
| Rosacea: a review of current topical, systemic and light-based therapies. | G Ital Dermatol Venereol | 2009 Dec | 19907406 |
| Acne vulgaris. | BMJ Clin Evid | 2008 May 15 | 19450306 |
Targets
- General Function:
- Steroid binding
- Specific Function:
- Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
- Gene Name:
- AKR1D1
- Uniprot ID:
- P51857
- Molecular Weight:
- 37376.615 Da
References
- Stamatiadis D, Bulteau-Portois MC, Mowszowicz I: Inhibition of 5 alpha-reductase activity in human skin by zinc and azelaic acid. Br J Dermatol. 1988 Nov;119(5):627-32. [3207614 ]
- General Function:
- Sterol 5-alpha reductase activity
- Specific Function:
- Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
- Gene Name:
- SRD5A2
- Uniprot ID:
- P31213
- Molecular Weight:
- 28393.015 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
- Gene Name:
- TYR
- Uniprot ID:
- P14679
- Molecular Weight:
- 60392.69 Da
References
- Schallreuter KU, Wood JW: A possible mechanism of action for azelaic acid in the human epidermis. Arch Dermatol Res. 1990;282(3):168-71. [2114832 ]
- 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 ]