Livestock Metabolome Database: Showing metabocard for Azelaic acid (LMDB00245)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:34 UTC

Update Date

2016-07-20 20:58:41 UTC

Lmdb

LMDB00245

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Azelaic acid

Description

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,7-Dicarboxyheptane	ChEBI
1,7-Heptanedicarboxylic acid	ChEBI
1,9-Nonanedioic acid	ChEBI
Acide azelaique	ChEBI
Acidum azelaicum	ChEBI
Anchoic acid	ChEBI
Azelainsaeure	ChEBI
Azelex	ChEBI
Finacea	ChEBI
Lepargylic acid	ChEBI
N-Nonanedioic acid	ChEBI
Nonandisaeure	ChEBI
Skinoren	ChEBI
Nonanedioic acid	Kegg
1,7-Heptanedicarboxylate	Generator
1,9-Nonanedioate	Generator
Anchoate	Generator
Lepargylate	Generator
N-Nonanedioate	Generator
Nonanedioate	Generator
Azelaate	Generator
Azalaic acid	HMDB
Azelaicacidtech	HMDB
Azelainic acid	HMDB
Azelate	HMDB
Emerox 1110	HMDB
Emerox 1144	HMDB
Emery'S L-110	HMDB
Finevin	HMDB
Heptanedicarboxylic acid	HMDB
Nonanedioic acid azelaic acid	HMDB
Nonanedioic acid homopolymer	HMDB
Poly(azelaic anhydride)	HMDB
Polyazelaic anhydride	HMDB
Skinorem	HMDB
Azelaic acid, dilithium salt	HMDB
Azelaic acid, dipotassium salt	HMDB
Azelaic acid, disodium salt	HMDB
Azelaic acid, monosodium salt	HMDB
Azelaic acid, potassium salt	HMDB
Azelaic acid, sodium salt	HMDB
Monosodium azelate	HMDB
Azelaic acid	PhytoBank
Azelic acid	PhytoBank
alpha,omega-Nonanedioic acid	PhytoBank
α,ω-Nonanedioic acid	PhytoBank

Chemical Formula

C₉H₁₆O₄

Average Molecular Weight

188.2209

Monoisotopic Molecular Weight

188.104859

IUPAC Name

nonanedioic acid

Traditional Name

azelaic acid

CAS Registry Number

123-99-9

SMILES

OC(=O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)

InChI Key

BDJRBEYXGGNYIS-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:48131 )
Dicarboxylic acids (C08261 )
Dicarboxylic acids (LMFA01170054 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.37	ALOGPS
logP	1.82	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.15	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	46.54 m³·mol⁻¹	ChemAxon
Polarizability	20.5 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0v0r-4920000000-5a3ed693b1c4083f1f15	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0v0r-4920000000-5a3ed693b1c4083f1f15	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-1910000000-83ba58dac4b0698643d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9600000000-24638c458fa83f47c259	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00y0-9740000000-d157d08c3a7c87244190	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0900000000-a118e433f0bd27a95b89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-006t-9600000000-93b3a375b722791cb5c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-052k-9500000000-6b069f2fed947651b284	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-7980b5eadcca6ee1eadd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-462585874f7661d40d5b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9300000000-d654ca3c764066f98358	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-9000000000-60a08bb384f2b4cbfca8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-7980b5eadcca6ee1eadd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-462585874f7661d40d5b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9300000000-fcefbd80852c2625bc0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-60a08bb384f2b4cbfca8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-26216115e75cad833509	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-7bef8272c481ea57a60b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-751bf479539d4bd2b5e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-9a056a45b27896966bf9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-3155fd845eec8f32ce93	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004r-0900000000-544110f97ebc0f97e15b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0900000000-b1b7c1ab57d58a2405a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g3-2900000000-d0ba7fbbe987efa4c818	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05qd-9100000000-8d65a19b998d18ad08ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a7edc3ac66d27685b9d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-1900000000-c56b9d972f88c58dc65b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-47cbefe19a788d7f36b9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06rx-9100000000-6db2acb47ad4c6163063	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Ruminal Fluid
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22675387	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details

External Links

DrugBank ID

DB00548

HMDB ID

HMDB0000784

FooDB ID

FDB012192

Phenol Explorer ID

Not Available

KNApSAcK ID

C00045634

BiGG ID

Not Available

BioCyc ID

CPD0-1265

METLIN ID

5750

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB21399

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Nguyen QH, Bui TP: Azelaic acid: pharmacokinetic and pharmacodynamic properties and its therapeutic role in hyperpigmentary disorders and acne. Int J Dermatol. 1995 Feb;34(2):75-84. [7737781 ]
Mackrides PS, Shaughnessy AF: Azelaic acid therapy for acne. Am Fam Physician. 1996 Dec;54(8):2457-9. [8961845 ]

Showing metabocard for Azelaic acid (LMDB00245)

Structure for LMDB00245 (Azelaic acid)