Azelaic Acid
PubChem CID: 2266
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| Compound Synonyms | azelaic acid, NONANEDIOIC ACID, 123-99-9, Finacea, Anchoic acid, Azelex, Lepargylic acid, 1,7-Heptanedicarboxylic acid, Skinoren, 1,9-Nonanedioic acid, Heptanedicarboxylic acid, n-Nonanedioic acid, Emerox 1110, Emerox 1144, acide azelaique, azelate, Acido azelaico, acidum azelaicum, Finevin, Azelainic acid, 1,7-Dicarboxyheptane, Azelaic acid, technical grade, Skinorem, ZK 62498, ZK-62498, Emery's L-110, Acidum azelaicum [Latin], NSC 19493, Azelainsaeure, Nonandisaeure, CHEBI:48131, UNII-F2VW3D43YT, EINECS 204-669-1, F2VW3D43YT, NSC-19493, BRN 1101094, DTXSID8021640, AI3-06299, HSDB 7659, NSC19493, MFCD00004432, MLS000069659, DTXCID501640, EC 204-669-1, 4-02-00-02055 (Beilstein Handbook Reference), NCGC00014993-07, SMR000059164, Acidum azelaicum (Latin), Azalaic Acid, Acide azelaique [French], Acido azelaico [Spanish], AZELAIC ACID (MART.), AZELAIC ACID [MART.], heptane-1,7-dicarboxylic acid, Azelaic acid [USAN:INN], Azelaic, CAS-123-99-9, Finacea (TN), Azelaic acid 99%, Azelex (TN), SR-01000075671, Azelaic acid (USAN/INN), Azelaicacidtech, Azelainsaure, Lepargylate, Nonandisaure, Anchoate, azelaic-acid, n-Nonanedioate, Acidum acelaicum, Finacea Foam, 1tuf, Azelaic Acid Gel, 1,9-Nonanedioate, SH-441, AGN-191861, Azelaic acid, 98%, Spectrum_000057, Water-solubleazelaicacid, Opera_ID_740, Azelaic acid (Standard), 1,7-Heptanedicarboxylate, Spectrum2_000995, Spectrum3_000278, Spectrum4_000401, Spectrum5_001304, Water-soluble azelaic acid, AZELAIC ACID [MI], Epitope ID:187039, AZELAIC ACID [INN], Lopac-246379, SCHEMBL3887, AZELAIC ACID [HSDB], AZELAIC ACID [USAN], CHEMBL1238, Lopac0_000051, AZELAIC ACID [VANDF], BSPBio_001756, KBioGR_000662, KBioSS_000437, Nonanedioic acid Azelaic acid, MLS001148615, BIDD:GT0315, DivK1c_000532, SPECTRUM1500648, SPBio_001089, AZELAIC ACID [WHO-DD], GTPL7484, HMS501K14, HY-B0704R, KBio1_000532, KBio2_000437, KBio2_003005, KBio2_005573, KBio3_001256, Azelaic acid, analytical standard, D10AX03, NINDS_000532, HMS1921O11, HMS2092E22, HMS2234D10, HMS3260K03, HMS3372J07, Pharmakon1600-01500648, AZELAIC ACID [ORANGE BOOK], BCP18690, HY-B0704, Tox21_110063, Tox21_201989, Tox21_303011, Tox21_500051, Azelaic acid, technical grade, 80%, CCG-40081, LMFA01170054, NSC757406, s4550, STL059432, AKOS000120052, Tox21_110063_1, Azelaic acid, technical, ~85% (GC), Azelaic acid, Vetec(TM) reagent grade, DB00548, FA29685, KS-5293, LP00051, NSC-757406, SDCCGMLS-0066619.P001, SDCCGMLS-0066619.P033, SDCCGSBI-0050040.P004, IDI1_000532, MLS-0066619, NCGC00014993-01, NCGC00014993-02, NCGC00014993-03, NCGC00014993-04, NCGC00014993-05, NCGC00014993-06, NCGC00014993-08, NCGC00014993-09, NCGC00014993-10, NCGC00014993-12, NCGC00014993-15, NCGC00093565-01, NCGC00093565-02, NCGC00093565-03, NCGC00093565-04, NCGC00093565-05, NCGC00093565-06, NCGC00093565-07, NCGC00256508-01, NCGC00259538-01, NCGC00260736-01, BP-27863, MLS-0066619.P021, SBI-0050040.P003, A0561, A1318, Dicarboxylic acid C9, Nonanedioic acid, AZA, EU-0100051, NS00011498, EN300-18040, C08261, D03034, D70171, AB00052140_12, Q413504, SR-01000075671-1, SR-01000075671-4, SR-01000075671-6, 0C50D8EC-0DB0-4F24-8EFC-2919E1F0D9BF, BRD-K08976401-001-18-5, Z57127532, F8889-5093, 204-669-1, InChI=1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13 |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 74.6 |
| Hydrogen Bond Donor Count | 2.0 |
| Pfizer 3 75 Rule | False |
| Np Classifier Class | Dicarboxylic acids |
| Deep Smiles | OC=O)CCCCCCCC=O)O |
| Heavy Atom Count | 13.0 |
| Classyfire Class | Fatty acyls |
| Description | Occurs in rancid fats. Isolated from a few higher plants Azelaic acid (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH). It possesses a variety of biological actions both in vitro and in vivo. Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. Later, it was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: it possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids. Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris. It offers effectiveness similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845), Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by <i>Malassezia furfur</i> (also known as <i>Pityrosporum ovale</i>), 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., 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%. Azelaic acid may be useful as a hair growth stimulant.[citation needed]. Azelaic acid is found in common bean and potato. |
| Classyfire Subclass | Fatty acids and conjugates |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 147.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;imppat_phytochem;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Enzyme Uniprot Id | P51857, P31213 |
| Uniprot Id | P14679, P51857, P31213 |
| Iupac Name | nonanedioic acid |
| Class | Fatty Acyls |
| Veber Rule | True |
| Classyfire Superclass | Lipids and lipid-like molecules |
| Xlogp | 1.6 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Fatty acids and conjugates |
| Gsk 4 400 Rule | True |
| Molecular Formula | C9H16O4 |
| Inchi Key | BDJRBEYXGGNYIS-UHFFFAOYSA-N |
| Silicos It Class | Soluble |
| Rotatable Bond Count | 8.0 |
| State | Solid |
| Synonyms | 1, 9-Nonanedioic acid, 1,7-Dicarboxyheptane, 1,7-Heptanedicarboxylate, 1,7-Heptanedicarboxylic acid, 1,9-Nonanedioate, 1,9-Nonanedioic acid, 1tuf, Acide azelaique, Acido azelaico, Acidum azelaicum, Anchoate, Anchoic acid, Azalaic acid, Azelaate, Azelaic acid, Azelaic acid (usan/inn), Azelaic acid [usan:inn], Azelaic acid polyanhydride, AZELAIC ACID, 95%, Azelaic acid, INN, USAN, Azelaic polyanhydride, Azelaicacidtech, Azelainic acid, Azelainsaeure, Azelate, Azelex, Azelex (TN), Azleaic acid, Emerox 1110, Emerox 1144, Emery's L-110, Finacea, Finacea (TN), Finevin, Heptanedicarboxylic acid, Lepargylate, Lepargylic acid, N-nonanedioate, N-nonanedioic acid, Nonandisaeure, Nonanedioate, Nonanedioic acid, Nonanedioic acid azelaic acid, Nonanedioic acid homopolymer, Nonanedioic acid, homopolymer, Poly(azelaic anhydride), Polyazelaic anhydride, Skinorem, Skinoren, ZK 62498, N-Nonanedioic acid, N-Nonanedioate, Emery'S L-110, Azelaic acid, dilithium salt, Azelaic acid, dipotassium salt, Azelaic acid, disodium salt, Azelaic acid, monosodium salt, Azelaic acid, potassium salt, Azelaic acid, sodium salt, Monosodium azelate, Azelic acid, alpha,omega-Nonanedioic acid, α,ω-Nonanedioic acid, azelaic acid, nonanedioic acid, nonanedioic-acid |
| Substituent Name | Medium-chain fatty acid, Dicarboxylic acid or derivatives, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aliphatic acyclic compound |
| Esol Class | Very soluble |
| Functional Groups | CC(=O)O |
| Compound Name | Azelaic Acid |
| Kingdom | Organic compounds |
| Exact Mass | 188.105 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 188.105 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 188.22 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic acyclic compounds |
| Lipinski Rule Of 5 | True |
| 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) |
| Smiles | C(CCCC(=O)O)CCCC(=O)O |
| Np Classifier Biosynthetic Pathway | Fatty acids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Medium-chain fatty acids |
| Np Classifier Superclass | Fatty Acids and Conjugates |
- 1. Outgoing r'ship
FOUND_INto/from Baccharoides Anthelmintica (Plant) Rel Props:Reference:ISBN:9788172363093 - 2. Outgoing r'ship
FOUND_INto/from Hibiscus Syriacus (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279 - 3. Outgoing r'ship
FOUND_INto/from Phaseolus Vulgaris (Plant) Rel Props:Source_db:fooddb_chem_all - 4. Outgoing r'ship
FOUND_INto/from Solanum Tuberosum (Plant) Rel Props:Source_db:fooddb_chem_all