MiMeDB: Showing metabocard for Azelaic acid (MMDBc0000546)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:14 UTC

Update Date

2024-04-30 19:32:57 UTC

Metabolite ID

MMDBc0000546

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

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

Molecular Formula

C₉H₁₆O₄

Average Mass

188.2209

Monoisotopic Mass

188.104859

IUPAC Name

nonanedioic acid

Traditional Name

azelaic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0v0r-4920000000-5a3ed693b1c4083f1f15	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0v0r-4920000000-5a3ed693b1c4083f1f15	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-1910000000-83ba58dac4b0698643d0	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9600000000-24638c458fa83f47c259	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00y0-9740000000-d157d08c3a7c87244190	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0900000000-a118e433f0bd27a95b89	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-006t-9600000000-93b3a375b722791cb5c9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-052k-9500000000-6b069f2fed947651b284	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-7980b5eadcca6ee1eadd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-462585874f7661d40d5b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9300000000-d654ca3c764066f98358	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-9000000000-60a08bb384f2b4cbfca8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-7980b5eadcca6ee1eadd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-462585874f7661d40d5b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9300000000-fcefbd80852c2625bc0e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-60a08bb384f2b4cbfca8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-26216115e75cad833509	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-7bef8272c481ea57a60b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-751bf479539d4bd2b5e1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-9a056a45b27896966bf9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-3155fd845eec8f32ce93	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004r-0900000000-544110f97ebc0f97e15b	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0900000000-b1b7c1ab57d58a2405a8	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g3-2900000000-d0ba7fbbe987efa4c818	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05qd-9100000000-8d65a19b998d18ad08ac	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a7edc3ac66d27685b9d1	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-1900000000-c56b9d972f88c58dc65b	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-47cbefe19a788d7f36b9	2015-04-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06rx-9100000000-6db2acb47ad4c6163063	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)		2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

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

Tissue Locations

Epidermis
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191760	Tyrosinase	Unknown	P14679	Homo sapiens
MMDBp0192197	3-oxo-5-beta-steroid 4-dehydrogenase	Enzyme	P51857	Homo sapiens
MMDBp0192337	3-oxo-5-alpha-steroid 4-dehydrogenase 2	Enzyme	P31213	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0004776	1-Hydroperoxy-8-Carboxyoctyl 3,4-Epoxynon-(2E)-Enyl Ether	Azelaic acid	Not Available		VMH	11408659 11686005
MMDBr0004777	1-Hydroperoxy-8-Carboxyoctyl 3,4-Epoxynon-(2E)-Enyl Ether	Azelaic acid	Not Available		VMH	11408659 11686005
MMDBr0005715	Azelaic acid	Azelaic acid	Not Available		VMH	30371894
MMDBr0038946	Azelaic acid	N-Nonanedioyl-4R-hydroxysphinganine	Alkaline ceramidase YPC1	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	8	Human stool; Human feces; Human mucosa; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	1		Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Root	Phaseolus vulgaris	FooDB	31437929
Plant	Leaves	Solanum tuberosum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified			0	2.1	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	3.8	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	4.4	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0.45	0.81	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.50	1.2	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			1.0	6.3	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified	1.9		1.2	3.2	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Breast milk	Detected and Quantified	101	72.5			uM	Adult (>18 years old)	Female	Normal	HMDB	24027187
Human Cerebrospinal fluid (csf)	Detected and Quantified	17.0	17.0			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	8412012
Human Urine	Detected and Quantified	2.21	1.67			umol/mmol creatinine	Adult (>18 years old)	Both		HMDB	9439441
Human Urine	Detected and Quantified	2.5		0.1	12.3	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	2.8		1.8	4.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	27.0		0.0	58.0	uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Urine	Detected and Quantified	3.6		0.1	4.4	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	3.7		0.6	17.6	umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	4.3		1.0	11.7	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	4.8		1.3	15	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected and Quantified	4.791	3.255			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	7.782	5.227			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.382	1.998			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	8.033	4.649			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Saliva	Detected and Quantified	0.0648	0.127			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.221	0.218			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.69	0.876			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.73	1.02			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	2.06	1.85			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	2.74	1.71			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	9439441
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Sweat	Detected but not Quantified						Adult	Both	Normal	HMDB	26755145
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000784

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.2165/00003495-199141050-00007. [PubMed:1712709 ]
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 ]
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. doi: 10.1111/j.1365-4362.1995.tb03583.x. [PubMed:7737781 ]
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. doi: 10.1007/BF00711898. [PubMed:8412012 ]
Mackrides PS, Shaughnessy AF: Azelaic acid therapy for acne. Am Fam Physician. 1996 Dec;54(8):2457-9. [PubMed:8961845 ]
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 ]
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. doi: 10.1023/a:1005624523611. [PubMed:10896310 ]
Webster G: Combination azelaic acid therapy for acne vulgaris. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S47-50. doi: 10.1067/mjd.2000.108318. [PubMed:10898830 ]
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. doi: 10.1159/000018473. [PubMed:11053913 ]
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. doi: 10.1517/14656566.5.1.5. [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. doi: 10.2165/00128071-200405010-00009. [PubMed:14979745 ]
Halder RM, Richards GM: Management of dyschromias in ethnic skin. Dermatol Ther. 2004;17(2):151-7. doi: 10.1111/j.1396-0296.2004.04015.x. [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 ]
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Showing metabocard for Azelaic acid (MMDBc0000546)

MOL for #<Metabolite:0x000055e070e1bf58>

3D MOL for #<Metabolite:0x000055e070e1bf58>

3D SDF for #<Metabolite:0x000055e070e1bf58>

3D-SDF for #<Metabolite:0x000055e070e1bf58>

PDB for #<Metabolite:0x000055e070e1bf58>

3D PDB for #<Metabolite:0x000055e070e1bf58>

SMILES for #<Metabolite:0x000055e070e1bf58>

INCHI for #<Metabolite:0x000055e070e1bf58>

Structure for #<Metabolite:0x000055e070e1bf58>

3D Structure for #<Metabolite:0x000055e070e1bf58>