NP-MRD: Showing NP-Card for Azelaic acid (NP0000459)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...Show more...

Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-03 04:18:55 UTC

NP-MRD ID

NP0000459

Natural Product DOI

https://doi.org/10.57994/1562

Secondary Accession Numbers

None

Natural Product 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000784
     RDKit          3D
Azelaic acid
 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.9974    0.0468   -2.2837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4621    0.1986   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1988    0.8011   -0.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -0.2451   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7426    0.0311    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358   -0.3951    0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821    0.3024    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607   -0.2322    0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163    0.4026   -0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848   -0.1914    0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954    0.3346   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    1.1937   -1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313   -0.1326    0.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588    0.6277    0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3524    0.1777   -1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602   -1.3448   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069   -0.6156    1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002    1.0654    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.0857    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735   -1.4713    0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3834    0.1293   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2740    1.3887    0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -1.3169    0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1129   -0.0085    1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1714   -1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034    1.5065   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    0.0262    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670   -1.2851    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2578   -1.0794   -0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

HMDB0000784
     RDKit          3D
Azelaic acid
 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.9974    0.0468   -2.2837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4621    0.1986   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1988    0.8011   -0.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -0.2451   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7426    0.0311    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358   -0.3951    0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821    0.3024    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607   -0.2322    0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163    0.4026   -0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848   -0.1914    0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954    0.3346   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    1.1937   -1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313   -0.1326    0.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588    0.6277    0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3524    0.1777   -1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602   -1.3448   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069   -0.6156    1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002    1.0654    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.0857    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735   -1.4713    0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3834    0.1293   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2740    1.3887    0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -1.3169    0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1129   -0.0085    1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1714   -1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034    1.5065   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    0.0262    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670   -1.2851    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2578   -1.0794   -0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8643.6608640.575   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8644.9928639.806   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8646.3288640.575   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8647.6648639.806   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8646.3288642.116   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8642.3218639.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8640.9878640.575   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8639.6528639.806   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8638.3188640.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8636.9838639.806   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8635.6488640.575   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8634.3148639.806   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8635.6488642.116   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0000784
HETATM    1  O1  UNL     1      -4.997   0.047  -2.284  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.462   0.199  -1.158  1.00  0.00           C  
HETATM    3  O2  UNL     1      -5.199   0.801  -0.163  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.083  -0.245  -0.880  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.743   0.031   0.544  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.336  -0.395   0.901  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.282   0.302   0.084  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.061  -0.232   0.563  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.216   0.403  -0.192  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.485  -0.191   0.356  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.695   0.335  -0.284  1.00  0.00           C  
HETATM   12  O3  UNL     1       4.663   1.194  -1.196  1.00  0.00           O  
HETATM   13  O4  UNL     1       5.931  -0.133   0.132  1.00  0.00           O  
HETATM   14  H1  UNL     1      -4.959   0.628   0.795  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.352   0.178  -1.600  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.060  -1.345  -1.043  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.407  -0.616   1.173  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.900   1.065   0.848  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.176  -0.086   1.959  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.174  -1.471   0.852  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.383   0.129  -1.004  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.274   1.389   0.310  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.050  -1.317   0.399  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.113  -0.009   1.645  1.00  0.00           H  
HETATM   25  H12 UNL     1       2.109   0.171  -1.271  1.00  0.00           H  
HETATM   26  H13 UNL     1       2.203   1.506  -0.100  1.00  0.00           H  
HETATM   27  H14 UNL     1       3.536   0.026   1.450  1.00  0.00           H  
HETATM   28  H15 UNL     1       3.467  -1.285   0.261  1.00  0.00           H  
HETATM   29  H16 UNL     1       6.258  -1.079  -0.042  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   12   13
CONECT   13   29
END

HMDB0000784
     RDKit          3D
Azelaic acid
 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.9974    0.0468   -2.2837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4621    0.1986   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1988    0.8011   -0.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -0.2451   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7426    0.0311    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358   -0.3951    0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821    0.3024    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607   -0.2322    0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163    0.4026   -0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848   -0.1914    0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954    0.3346   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632    1.1937   -1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313   -0.1326    0.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9588    0.6277    0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3524    0.1777   -1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0602   -1.3448   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4069   -0.6156    1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9002    1.0654    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763   -0.0857    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735   -1.4713    0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3834    0.1293   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2740    1.3887    0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -1.3169    0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1129   -0.0085    1.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.1714   -1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034    1.5065   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    0.0262    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4670   -1.2851    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2578   -1.0794   -0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

View in JSmol

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
Azelic acid	HMDB
alpha,Omega-nonanedioic acid	HMDB
Α,ω-nonanedioic acid	HMDB
Azelaic acid	PhytoBank

Chemical Formula

C₉H₁₆O₄

Average Mass

188.2209 Da

Monoisotopic Mass

188.10486 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	Not Available	Sumner lab, University of Missouri	Zach Tretter	2024-01-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acorus calamus	LOTUS Database	35616633
Aloe africana	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Averrhoa carambola	KNApSAcK Database	22123792
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brucea javanica	LOTUS Database	35616633
Bubalus bubalis	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Carthamus oxyacanthus	LOTUS Database	35616633
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Fritillaria hupehensis	LOTUS Database	35616633
Fritillaria monantha	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Hibiscus syriacus	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Hyacinthoides non-scripta	LOTUS Database	35616633
Isatis tinctoria	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Lotus burttii	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Peucedanum praeruptorum	LOTUS Database	35616633
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Ranunculus ternatus	LOTUS Database	35616633
Salmonella enterica	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Schnabelia tetradonta	KNApSAcK Database	22123792
Solanum lycopersicum	LOTUS Database	35616633
Solanum tuberosum	KNApSAcK Database	22123792
Streptomyces nigra	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Tuber indicum	LOTUS Database	35616633
Vincetoxicum atratum	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	106.5 °C	Not Available
Boiling Point	356.00 to 357.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.4 mg/mL	Not Available
LogP	1.57	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	2.28 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000784

DrugBank ID

DB00548

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Azelaic_Acid

METLIN ID

5750

PubChem Compound

2266

PDB ID

Not Available

ChEBI ID

48131

Good Scents ID

rw1220821

References

General References

Mayer-da-Silva A, Gollnick H, Detmar M, Gassmuller J, Parry A, Muller R, Orfanos CE: Effects of azelaic acid on sebaceous gland, sebum excretion rate and keratinization pattern in human skin. An in vivo and in vitro study. Acta Derm Venereol Suppl (Stockh). 1989;143:20-30. [PubMed:2475995 ]
Hermanns JF, Petit L, Martalo O, Pierard-Franchimont C, Cauwenbergh G, Pierard GE: Unraveling the patterns of subclinical pheomelanin-enriched facial hyperpigmentation: effect of depigmenting agents. Dermatology. 2000;201(2):118-22. [PubMed:11053913 ]
Rocamora V, Puig L, Romani J, de Moragas JM: Amelanotic lentigo maligna melanoma: report of a case and review of the literature. Cutis. 1999 Jul;64(1):53-6. [PubMed:10431675 ]
Russell JJ: Topical therapy for acne. Am Fam Physician. 2000 Jan 15;61(2):357-66. [PubMed:10670502 ]
Webster G: Combination azelaic acid therapy for acne vulgaris. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S47-50. [PubMed:10898830 ]
Del Rosso JQ: Medical treatment of rosacea with emphasis on topical therapies. Expert Opin Pharmacother. 2004 Jan;5(1):5-13. [PubMed:14680431 ]
Frampton JE, Wagstaff AJ: Azelaic acid 15% gel: in the treatment of papulopustular rosacea. Am J Clin Dermatol. 2004;5(1):57-64. [PubMed:14979745 ]
Halder RM, Richards GM: Topical agents used in the management of hyperpigmentation. Skin Therapy Lett. 2004 Jun-Jul;9(6):1-3. [PubMed:15334278 ]
Wolf JE Jr: Present and future rosacea therapy. Cutis. 2005 Mar;75(3 Suppl):4-7; discussion 33-6. [PubMed:15810803 ]
van Zuuren EJ, Graber MA: The rigor of trials evaluating Rosacea treatments. Cutis. 2005 Mar;75(3 Suppl):13-6; discussion 33-6. [PubMed:15810805 ]
Nally JB, Berson DS: Topical therapies for rosacea. J Drugs Dermatol. 2006 Jan;5(1):23-6. [PubMed:16468288 ]
Fleischer AB Jr: The evolution of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):4-6. [PubMed:16566281 ]
Draelos ZD: The rationale for advancing the formulation of azelaic acid vehicles. Cutis. 2006 Feb;77(2 Suppl):7-11. [PubMed:16566282 ]
Elewski B, Thiboutot D: A clinical overview of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):12-6. [PubMed:16566283 ]
Del Rosso JQ: The use of topical azelaic acid for common skin disorders other than inflammatory rosacea. Cutis. 2006 Feb;77(2 Suppl):22-4. [PubMed:16566285 ]
Worret WI, Fluhr JW: [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid]. J Dtsch Dermatol Ges. 2006 Apr;4(4):293-300. [PubMed:16638058 ]
Liu RH, Smith MK, Basta SA, Farmer ER: Azelaic acid in the treatment of papulopustular rosacea: a systematic review of randomized controlled trials. Arch Dermatol. 2006 Aug;142(8):1047-52. [PubMed:16924055 ]
Gupta AK, Gover MD, Nouri K, Taylor S: The treatment of melasma: a review of clinical trials. J Am Acad Dermatol. 2006 Dec;55(6):1048-65. Epub 2006 Sep 28. [PubMed:17097400 ]
Fitton A, Goa KL: Azelaic acid. A review of its pharmacological properties and therapeutic efficacy in acne and hyperpigmentary skin disorders. Drugs. 1991 May;41(5):780-98. [PubMed:1712709 ]
van Zuuren EJ, Gupta AK, Gover MD, Graber M, Hollis S: Systematic review of rosacea treatments. J Am Acad Dermatol. 2007 Jan;56(1):107-15. Epub 2006 Nov 7. [PubMed:17190628 ]
Gupta AK, Gover MD: Azelaic acid (15% gel) in the treatment of acne rosacea. Int J Dermatol. 2007 May;46(5):533-8. [PubMed:17472690 ]
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. [PubMed:7737781 ]
Mackrides PS, Shaughnessy AF: Azelaic acid therapy for acne. Am Fam Physician. 1996 Dec;54(8):2457-9. [PubMed:8961845 ]

Showing NP-Card for Azelaic acid (NP0000459)

MOL for NP0000459 (Azelaic acid)

3D MOL for NP0000459 (Azelaic acid)

3D SDF for NP0000459 (Azelaic acid)

3D-SDF for NP0000459 (Azelaic acid)

PDB for NP0000459 (Azelaic acid)

3D PDB for NP0000459 (Azelaic acid)

SMILES for NP0000459 (Azelaic acid)

INCHI for NP0000459 (Azelaic acid)

Structure for NP0000459 (Azelaic acid)

3D Structure for NP0000459 (Azelaic acid)