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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:10 UTC

HMDB ID

HMDB0000784

Secondary Accession Numbers

HMDB00784

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 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 View NMR Assignments View Stereo Labels

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

Physiological effect

Health effect

Observation

Attachment loss (HMDB: HMDB0000784)
Missing teeth (HMDB: HMDB0000784)

Intervention

Periodontal Probing Depth (HMDB: HMDB0000784)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8412012)
Breast milk (PMID: 24027187)
Cerebrospinal Fluid (CSF) (PMID: 8412012)
Saliva (PMID: 22308371)
Breast milk (HMDB: HMDB0000784)
Cerebrospinal fluid (HMDB: HMDB0000784)

Tissue

Epithelium

Epidermis (HMDB: HMDB0000784)

Organ

Prostate (HMDB: HMDB0000784)
Skin (HMDB: HMDB0000784)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 19573517)
Sweat (PMID: 26755145)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0000784)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0000784)

Enteral

Ingestion (HMDB: HMDB0000784)

Source

Exogenous

Exogenous (HMDB: HMDB0000784)

Food

Food (HMDB: HMDB0000784)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Tuber

Potato (FooDB: FOOD00175)

Pulse

Bean

Common bean (FooDB: FOOD00134)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0000784)

Endogenous

Endogenous (HMDB: HMDB0000784)

Plant

Plant (HMDB: HMDB0000784)
Fabaceae (HMDB: HMDB0000784)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000784)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000784)

Lipid metabolism pathway (HMDB: HMDB0000784)

Biochemical process

Lipid transport (HMDB: HMDB0000784)

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0000784)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0000784)

Pharmaceutical (HMDB: HMDB0000784)

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000251)

Biological role

Energy source (HMDB: HMDB0000784)
Anti acne (HMDB: HMDB0000784)
Anti bacterial (HMDB: HMDB0000784)
Anti hyperpigmentative (HMDB: HMDB0000784)
Anti leukemic (HMDB: HMDB0000784)
Anti melanomic (HMDB: HMDB0000784)
Anti melasmic (HMDB: HMDB0000784)
Anti proliferative (HMDB: HMDB0000784)
Cytotoxic (HMDB: HMDB0000784)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	106.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.4 mg/mL	Not Available
LogP	1.57	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	137.378	30932474
[M-H]-	Not Available	139.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000214

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	144.191	31661259
DarkChem	[M-H]-	140.945	31661259
AllCCS	[M+H]+	142.685	32859911
AllCCS	[M-H]-	143.779	32859911
DeepCCS	[M+H]+	141.964	30932474
DeepCCS	[M-H]-	138.196	30932474
DeepCCS	[M-2H]-	175.081	30932474
DeepCCS	[M+Na]+	150.788	30932474
AllCCS	[M+H]+	142.7	32859911
AllCCS	[M+H-H2O]+	139.0	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.1	32859911
AllCCS	[M-H]-	143.8	32859911
AllCCS	[M+Na-2H]-	145.1	32859911
AllCCS	[M+HCOO]-	146.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azelaic acid	OC(=O)CCCCCCCC(O)=O	2556.0	Standard polar	33892256
Azelaic acid	OC(=O)CCCCCCCC(O)=O	1475.1	Standard non polar	33892256
Azelaic acid	OC(=O)CCCCCCCC(O)=O	1675.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Azelaic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCC(=O)O	1709.5	Semi standard non polar	33892256
Azelaic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCC(=O)O[Si](C)(C)C	1812.6	Semi standard non polar	33892256
Azelaic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(=O)O	1956.6	Semi standard non polar	33892256
Azelaic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2282.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Azelaic acid GC-MS (2 TMS)	splash10-0v0r-4920000000-5a3ed693b1c4083f1f15	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Azelaic acid GC-MS (Non-derivatized)	splash10-0v0r-4920000000-5a3ed693b1c4083f1f15	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Azelaic acid GC-EI-TOF (Non-derivatized)	splash10-00mk-1910000000-83ba58dac4b0698643d0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azelaic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9600000000-24638c458fa83f47c259	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azelaic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00y0-9740000000-d157d08c3a7c87244190	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azelaic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azelaic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azelaic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azelaic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06rx-9100000000-6db2acb47ad4c6163063	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-000i-0900000000-a118e433f0bd27a95b89	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-006t-9600000000-93b3a375b722791cb5c9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-052k-9500000000-6b069f2fed947651b284	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-000i-0900000000-7980b5eadcca6ee1eadd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-004i-0900000000-462585874f7661d40d5b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0002-9300000000-d654ca3c764066f98358	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0002-9000000000-60a08bb384f2b4cbfca8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ , negative-QTOF	splash10-000i-0900000000-7980b5eadcca6ee1eadd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ , negative-QTOF	splash10-004i-0900000000-462585874f7661d40d5b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ , negative-QTOF	splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ , negative-QTOF	splash10-0002-9300000000-fcefbd80852c2625bc0e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid LC-ESI-QQ , negative-QTOF	splash10-0002-9000000000-60a08bb384f2b4cbfca8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid Linear Ion Trap , negative-QTOF	splash10-004i-0900000000-26216115e75cad833509	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid Linear Ion Trap , negative-QTOF	splash10-004i-0900000000-7bef8272c481ea57a60b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid Linear Ion Trap , negative-QTOF	splash10-004i-0900000000-751bf479539d4bd2b5e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid Linear Ion Trap , negative-QTOF	splash10-00di-0900000000-9a056a45b27896966bf9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid Linear Ion Trap , negative-QTOF	splash10-00di-0900000000-3155fd845eec8f32ce93	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azelaic acid , negative-QTOF	splash10-004r-0900000000-544110f97ebc0f97e15b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azelaic acid 10V, Positive-QTOF	splash10-00dr-0900000000-b1b7c1ab57d58a2405a8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azelaic acid 20V, Positive-QTOF	splash10-00g3-2900000000-d0ba7fbbe987efa4c818	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azelaic acid 40V, Positive-QTOF	splash10-05qd-9100000000-8d65a19b998d18ad08ac	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azelaic acid 10V, Negative-QTOF	splash10-000i-0900000000-a7edc3ac66d27685b9d1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azelaic acid 20V, Negative-QTOF	splash10-00kr-1900000000-c56b9d972f88c58dc65b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azelaic acid 40V, Negative-QTOF	splash10-0a4l-9300000000-47cbefe19a788d7f36b9	2015-04-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Epidermis
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	27.0 (0.0-58.0) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Breast Milk	Detected and Quantified	101 +/- 72.5 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	17.0 +/- 17.0 uM	Adult (>18 years old)	Not Specified	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Saliva	Detected and Quantified	0.0648 +/- 0.127 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	1.69 +/- 0.876 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.73 +/- 1.02 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.221 +/- 0.218 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2.06 +/- 1.85 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2.74 +/- 1.71 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	2.5 (0.1-12.3) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	3.6 (0.1-4.4) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	4.3 (1.0-11.7) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	3.7 (0.6-17.6) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	9439441	details
Urine	Detected and Quantified	2.21 +/- 1.67 umol/mmol creatinine	Adult (>18 years old)	Both	Not Available	9439441	details
Urine	Detected and Quantified	8.033 +/- 4.649 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.50-1.2 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	4.8 (1.3-15) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	5.382 +/- 1.998 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0-2.1 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	0-3.8 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	0-4.4 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	1.0-6.3 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	0.45-0.81 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	2.8 (1.8-4.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.9 (1.2-3.2) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	gastric cancer	21443661	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	superficial gastric cancer	21443661	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Urine	Detected and Quantified	7.782 +/- 5.227 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	10.726 +/- 11.681 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	4.791 +/- 3.255 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Stomach cancer
Yu L, Aa J, Xu J, Sun M, Qian S, Cheng L, Yang S, Shi R: Metabolomic phenotype of gastric cancer and precancerous stages based on gas chromatography time-of-flight mass spectrometry. J Gastroenterol Hepatol. 2011 Aug;26(8):1290-7. doi: 10.1111/j.1440-1746.2011.06724.x. [PubMed:21443661 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

137215 (Stomach cancer)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB00548

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

C08261

MarkerDB ID

MDB00000251

Good Scents ID

Not Available

References

Synthesis Reference

Chen, Song; Yan, Jinlong. Synthesis of azelaic acid by chemical oxidation with oleic acid. Pige Huagong (2003), 20(6), 31-35.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
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 ]
Korman SH, Mandel H, Gutman A: Characteristic urine organic acid profile in peroxisomal biogenesis disorders. J Inherit Metab Dis. 2000 Jun;23(4):425-8. [PubMed:10896310 ]
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: A status report on the medical management of rosacea: focus on topical therapies. Cutis. 2002 Nov;70(5):271-5. [PubMed:12469780 ]
Liao DC: Management of acne. J Fam Pract. 2003 Jan;52(1):43-51. [PubMed:12540312 ]
Del Rosso JQ: Medical treatment of rosacea with emphasis on topical therapies. Expert Opin Pharmacother. 2004 Jan;5(1):5-13. [PubMed:14680431 ]
Wolf JE Jr: The role of topical metronidazole in the treatment of rosacea. Cutis. 2004 Jan;73(1 Suppl):19-28. [PubMed:14959942 ]
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: Management of dyschromias in ethnic skin. Dermatol Ther. 2004;17(2):151-7. [PubMed:15113282 ]
Halder RM, Richards GM: Topical agents used in the management of hyperpigmentation. Skin Therapy Lett. 2004 Jun-Jul;9(6):1-3. [PubMed:15334278 ]
Lindow KB: Rosacea. An overview of diagnosis and management. Adv Nurse Pract. 2004 Dec;12(12):27-32. [PubMed:15615217 ]
Cayce KA, McMichael AJ, Feldman SR: Hyperpigmentation: an overview of the common afflictions. Dermatol Nurs. 2004 Oct;16(5):401-6, 413-6; quiz 417. [PubMed:15624705 ]
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 ]
Purdy S: Acne vulgaris. Clin Evid. 2005 Jun;(13):2038-59. [PubMed:16135322 ]
Roebuck HL: Face up to rosacea. Nurse Pract. 2005 Sep;30(9):24-30, 35; quiz 36-7. [PubMed:16151303 ]
Callender VD: Considerations for treating acne in ethnic skin. Cutis. 2005 Aug;76(2 Suppl):19-23. [PubMed:16164153 ]
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 ]
Goodman G: Managing acne vulgaris effectively. Aust Fam Physician. 2006 Sep;35(9):705-9. [PubMed:16969442 ]
Purdy S: Acne vulgaris. Clin Evid. 2006 Jun;(15):2183-201. [PubMed:16973084 ]
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 ]

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase 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

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. [PubMed:2114832 ]
Nazzaro-Porro M: Azelaic acid. J Am Acad Dermatol. 1987 Dec;17(6):1033-41. [PubMed:2963038 ]
Picardo M, Passi S, Sirianni MC, Fiorilli M, Russo GD, Cortesi E, Barile G, Breathnach AS, Nazzaro-Porro M: Activity of azelaic acid on cultures of lymphoma- and leukemia-derived cell lines, normal resting and stimulated lymphocytes and 3T3 fibroblasts. Biochem Pharmacol. 1985 May 15;34(10):1653-8. [PubMed:4004885 ]
Nazzaro-Porro M, Passi S, Balus L, Breathnach A, Martin B, Morpurgo G: Effect of dicarboxylic acids on lentigo maligna. J Invest Dermatol. 1979 Jun;72(6):296-305. [PubMed:448162 ]

Enzyme Details

2. 3-oxo-5-beta-steroid 4-dehydrogenase

General function:: Involved in oxidoreductase activity
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:: 32889.38

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. [PubMed:3207614 ]

Enzyme Details

3. 3-oxo-5-alpha-steroid 4-dehydrogenase 2

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase 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:: 28407.035

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
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. [PubMed:3207614 ]

Showing metabocard for Azelaic acid (HMDB0000784)

MOL for HMDB0000784 (Azelaic acid)

3D MOL for HMDB0000784 (Azelaic acid)

3D SDF for HMDB0000784 (Azelaic acid)

3D-SDF for HMDB0000784 (Azelaic acid)

PDB for HMDB0000784 (Azelaic acid)

3D PDB for HMDB0000784 (Azelaic acid)

SMILES for HMDB0000784 (Azelaic acid)

INCHI for HMDB0000784 (Azelaic acid)

Structure for HMDB0000784 (Azelaic acid)

3D Structure for HMDB0000784 (Azelaic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

References