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Compound InformationSONAR Target prediction
Name:

AZELAIC ACID

Unique Identifier:SPE01500648
MolClass: Checkout models in ver1.5 and ver1.0
Molecular Formula:
Molecular Weight:172.094 g/mol
X log p:-1.656  (online calculus)
Lipinksi Failures0
TPSA34.14
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptors Count:4
Rotatable Bond Count:8
Canonical Smiles:OC(=O)CCCCCCCC(O)=O
Class:alkane
Source:rancid fats and Lycopodium spp
Therapeutics:antiacne, antiproliferative agent
Generic_name:Azelaic Acid
Chemical_iupac_name:nonanedioic acid
Drug_type:Approved Drug
Pharmgkb_id:PA448516
Kegg_compound_id:C08261
Drugbank_id:APRD00812
Melting_point:106.5 oC
H2o_solubility:2400 mg/L (20°C)
Logp:1.646
Isoelectric_point:4.55
Cas_registry_number:123-99-9
Mass_spectrum:http://webbook.nist.gov/cgi/cbook.cgi?Spec=C123999&Index=0&Type=Mass&Large=on
Drug_category:Antineoplastic Agents; Dermatologic Agents; ATC:D10AX03
Indication:For the topical treatment of mild-to-moderate inflammatory acne vulgaris.
Pharmacology: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.
Mechanism_of_action:The exact mechanism of action of azelaic acid is not known. It is thought that
azelaic acid manifests its antibacterial effects by inhibiting the synthesis of
cellular protein in anaerobic and aerobic bacteria, especially Staphylococcus
epidermidis
and Propionibacterium acnes. In aerobic bacteria, azelaic
acid reversibly inhibits several oxidoreductive enzymes including tyrosinase,
mitochondrial enzymes of the respiratory chain, thioredoxin reductase,
5-alpha-reductase, and DNA polymerases. In anaerobic bacteria, azelaic acid impedes
glycolysis. Along with these actions, azelaic acid also improves acne vulgaris by
normalizing the keratin process and decreasing microcomedo formation. Azelaic acid
may be effective against both inflamed and noninflamed lesions. Specifically,
azelaic acid reduces the thickness of the stratum corneum, shrinks keratohyalin
granules by reducing the amount and distribution of filaggrin (a component of
keratohyalin) in epidermal layers, and lowers the number of keratohyalin granules.
Organisms_affected:Various aerobic and anaerobic microorganisms

Found: 205 nonactive as graph: single | with analogs 2 3 4 5 6 7 8 9 10  Next >> [205]
Species: 4932
Condition: BCK1
Replicates: 2
Raw OD Value: r im 0.8890±0.0269408
Normalized OD Score: sc h 1.0130±0.00898732
Z-Score: 0.6245±0.164586
p-Value: 0.535082
Z-Factor: -1.67062
Fitness Defect: 0.6253
Bioactivity Statement: Nonactive
Experimental Conditions
Library:Spectrum_ED
Plate Number and Position:2|D8
Drug Concentration:50.00 nM
OD Absorbance:595 nm
Robot Temperature:30.00 Celcius
Date:2010-08-10 YYYY-MM-DD
Plate CH Control (+):0.09300000000000001±0.00526
Plate DMSO Control (-):0.94575±0.01308
Plate Z-Factor:0.9370
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DBLink | Rows returned: 2052[1] << Back 1 2 3 4 5 6 7 8 9 10  Next >> [342]
8818 3-cyclopentylpropanoic acid
9318 2-ethylhexanoate; tin(+2) cation
9857 sodium hexadecanoate
9903 (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetrade
cahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
10130 2-(3-acetyl-2,2-dimethyl-cyclobutyl)acetic acid
10131 3-(carboxymethyl)-2,2-dimethyl-cyclobutane-1-carboxylic acid

internal high similarity DBLink | Rows returned: 29<< Back 1 2 3 4 5 Next >> 
SPE01500835 1.0000
BTB 12971 1.0000
JFD 01229 1.0000
FM 00078 1.0000
BTB 12972 1.0000
BTB 12973 1.0000

active | Cluster 13528 | Additional Members: 3 | Rows returned: 0

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