Jump To Section:

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

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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:32:49 UTC

Update Date

2022-11-23 21:48:33 UTC

HMDB ID

HMDB0249061

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzydamine

Description

Benzydamine, also known as bencidamina, belongs to the class of organic compounds known as indazoles. Indazoles are compounds containing an indazole, which is structurally characterized by a pyrazole fused to a benzene. Benzydamine is a very strong basic compound (based on its pKa). It may be used alone or as an adjunct to other therapy giving the possibility of increased therapeutic effect with little risk of interaction. Synthesis starts with the reaction of the N-benzyl derivative from methyl anthranilate with nitrous acid to give the N-nitroso derivative. Benzydamine has been used recreationally. Unlike other NSAIDs, it does not inhibit cyclooxygenase or lipooxygenase, and is not ulcerogenic. Please note there is an error in this section: US3318905 states that the nitroso derivative is reduced with sodium hydrosulfite (sodium dithionite) and not with sodium hyposulfite (sodium thiosulfate), as shown in the above scheme and stated in text. Alternatively, use of chloroacetamide in the alkylation step followed by acid hydrolysis produces bendazac instead. There are no contraindications to the use of benzydamine except for known hypersensitivity. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzydamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzydamine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0249061
     RDKit          3D
BENZYDAMINE
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.8944    2.1925    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439    1.3470   -0.4480 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    1.0576    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617    0.5017   -1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5629   -0.6414   -1.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -0.2969   -0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312   -1.4609   -0.4023 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -1.2251    0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4324   -0.0541    0.4442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522   -0.2632    0.9204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575    0.7754    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.2776    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6281    0.7074   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4538    1.1376   -1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9954    2.1780   -1.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608    2.7784   -1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9671    2.3272   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9335   -1.5823    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -2.3653    1.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854   -3.7295    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460   -4.3483    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772   -3.5629    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -2.1886    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6466    1.9630    1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9931    2.2809   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    3.2385    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7111    0.4785   -0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5553    2.0357    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751    0.5045    1.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0286    1.1500   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3977    0.0664   -1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3590   -1.2282   -2.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0206   -1.4024   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616    0.4442   -1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801    0.1355    0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    1.6529    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910    0.4066    2.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973   -0.1206    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4277    0.6536   -1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6249    2.5231   -2.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282    3.5952   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847    2.7759   -0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8738   -1.9090    1.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7149   -4.3573    1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6938   -5.4219    0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257   -4.0272   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  8  1  0
 17 12  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
M  END

  Mrv1533004161523312D          

 23 25  0  0  0  0            999 V2000
    4.2584    1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9728    1.5318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9728    2.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6873    1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018    1.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1162    1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8307    1.5318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5452    1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2989    1.4548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8509    0.8418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6714    0.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1563    0.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9768    0.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4617   -0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1261   -1.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3057   -1.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8207   -0.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4384    0.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6933   -0.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1413   -1.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3343   -1.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0794   -0.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6314    0.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  8 23  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249061

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCOC1=NN(CC2=CC=CC=C2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H23N3O/c1-21(2)13-8-14-23-19-17-11-6-7-12-18(17)22(20-19)15-16-9-4-3-5-10-16/h3-7,9-12H,8,13-15H2,1-2H3

> <INCHI_KEY>
CNBGNNVCVSKAQZ-UHFFFAOYSA-N

> <FORMULA>
C19H23N3O

> <MOLECULAR_WEIGHT>
309.413

> <EXACT_MASS>
309.184112373

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.62041708632231

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3-[(1-benzyl-1H-indazol-3-yl)oxy]propyl}dimethylamine

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.659847397

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.256663067303403

> <JCHEM_POLAR_SURFACE_AREA>
30.29

> <JCHEM_REFRACTIVITY>
105.56290000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tantum

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249061
     RDKit          3D
BENZYDAMINE
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.8944    2.1925    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439    1.3470   -0.4480 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    1.0576    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617    0.5017   -1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5629   -0.6414   -1.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -0.2969   -0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312   -1.4609   -0.4023 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -1.2251    0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4324   -0.0541    0.4442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522   -0.2632    0.9204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575    0.7754    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.2776    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6281    0.7074   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4538    1.1376   -1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9954    2.1780   -1.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608    2.7784   -1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9671    2.3272   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9335   -1.5823    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -2.3653    1.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854   -3.7295    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460   -4.3483    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772   -3.5629    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -2.1886    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6466    1.9630    1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9931    2.2809   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    3.2385    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7111    0.4785   -0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5553    2.0357    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751    0.5045    1.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0286    1.1500   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3977    0.0664   -1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3590   -1.2282   -2.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0206   -1.4024   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616    0.4442   -1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801    0.1355    0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    1.6529    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910    0.4066    2.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973   -0.1206    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4277    0.6536   -1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6249    2.5231   -2.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282    3.5952   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847    2.7759   -0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8738   -1.9090    1.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7149   -4.3573    1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6938   -5.4219    0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257   -4.0272   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  8  1  0
 17 12  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       7.949   2.089   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.283   2.859   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.283   4.399   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.616   2.089   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.950   2.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.284   2.089   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.617   2.859   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.951   2.089   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      17.358   2.716   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      18.388   1.571   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      19.920   1.732   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.825   0.486   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.357   0.647   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.262  -0.599   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.635  -2.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.104  -2.166   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.199  -0.920   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.618   0.238   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.094  -1.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.064  -2.371   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.557  -2.051   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.082  -0.587   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.112   0.558   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   10   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    8   18                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0249061
HETATM    1  C1  UNL     1       3.894   2.193   0.162  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.844   1.347  -0.448  1.00  0.00           N  
HETATM    3  C2  UNL     1       6.021   1.058   0.278  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.462   0.502  -1.494  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.563  -0.641  -1.204  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.224  -0.297  -0.641  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.431  -1.461  -0.402  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.150  -1.225   0.130  1.00  0.00           C  
HETATM    9  N2  UNL     1      -0.432  -0.054   0.444  1.00  0.00           N  
HETATM   10  N3  UNL     1      -1.652  -0.263   0.920  1.00  0.00           N  
HETATM   11  C7  UNL     1      -2.558   0.775   1.348  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.404   1.278   0.232  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.628   0.707  -0.021  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.454   1.138  -1.050  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.995   2.178  -1.827  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.761   2.778  -1.599  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.967   2.327  -0.569  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.933  -1.582   0.943  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.981  -2.365   1.313  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.885  -3.730   1.182  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.746  -4.348   0.681  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.677  -3.563   0.303  1.00  0.00           C  
HETATM   23  C19 UNL     1      -0.784  -2.189   0.439  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.647   1.963   1.219  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.993   2.281  -0.461  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.337   3.239   0.151  1.00  0.00           H  
HETATM   27  H4  UNL     1       6.711   0.478  -0.373  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.555   2.036   0.464  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.875   0.505   1.216  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.029   1.150  -2.315  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.398   0.066  -1.959  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.359  -1.228  -2.149  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.021  -1.402  -0.526  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.662   0.444  -1.222  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.380   0.136   0.386  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.985   1.653   1.753  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.191   0.407   2.169  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.997  -0.121   0.597  1.00  0.00           H  
HETATM   39  H16 UNL     1      -6.428   0.654  -1.221  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.625   2.523  -2.630  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.428   3.595  -2.227  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.985   2.776  -0.356  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.874  -1.909   1.705  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.715  -4.357   1.474  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.694  -5.422   0.586  1.00  0.00           H  
HETATM   46  H23 UNL     1       0.226  -4.027  -0.092  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4
CONECT    3   27   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8
CONECT    8    9    9   23
CONECT    9   10
CONECT   10   11   18
CONECT   11   12   36   37
CONECT   12   13   13   17
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   17   42
CONECT   18   19   19   23
CONECT   19   20   43
CONECT   20   21   21   44
CONECT   21   22   45
CONECT   22   23   23   46
END

HMDB0249061
     RDKit          3D
BENZYDAMINE
 46 48  0  0  0  0  0  0  0  0999 V2000
    3.8944    2.1925    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439    1.3470   -0.4480 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    1.0576    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617    0.5017   -1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5629   -0.6414   -1.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -0.2969   -0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4312   -1.4609   -0.4023 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -1.2251    0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4324   -0.0541    0.4442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522   -0.2632    0.9204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575    0.7754    1.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.2776    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6281    0.7074   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4538    1.1376   -1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9954    2.1780   -1.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608    2.7784   -1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9671    2.3272   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9335   -1.5823    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -2.3653    1.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854   -3.7295    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460   -4.3483    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772   -3.5629    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -2.1886    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6466    1.9630    1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9931    2.2809   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3368    3.2385    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7111    0.4785   -0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5553    2.0357    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751    0.5045    1.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0286    1.1500   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3977    0.0664   -1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3590   -1.2282   -2.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0206   -1.4024   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616    0.4442   -1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801    0.1355    0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    1.6529    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910    0.4066    2.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973   -0.1206    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4277    0.6536   -1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6249    2.5231   -2.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282    3.5952   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847    2.7759   -0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8738   -1.9090    1.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7149   -4.3573    1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6938   -5.4219    0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257   -4.0272   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  8  1  0
 17 12  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Benzyl-3-(3-(dimethylamino)propoxy)-1H-indazole	ChEBI
Bencidamina	ChEBI
Benzidamine	ChEBI
Benzindamine	ChEBI
Benzydamide	ChEBI
Benzydaminum	ChEBI
N,N-Dimethyl-3-[[1-(phenylmethyl)-3-indazolyl]oxy]-1-propanamine	ChEBI
Apo-benzydamine	Kegg
chefaro Brand OF benzydamine hydrochloride	MeSH
Difflam	MeSH
eipico Brand OF benzydamine hydrochloride	MeSH
Farma lepori brand OF benzydamine hydrochloride	MeSH
novo-Benzydamine	MeSH
Pharmascience brand OF benzydamine hydrochloride	MeSH
Sun-benz	MeSH
Benzydamine monohydrochloride	MeSH
PMS Benzydamine	MeSH
promeco Brand OF benzydamine hydrochloride	MeSH
Sun brand OF benzydamine hydrochloride	MeSH
Tantum	MeSH
Tantum topico	MeSH
Vantal brand OF benzydamine hydrochloride	MeSH
ratio Benzydamine	MeSH
3m Brand OF benzydamine hydrochloride	MeSH
CSC Brand OF benzydamine hydrochloride	MeSH
Hydrochloride, benzydamine	MeSH
Monohydrochloride, benzydamine	MeSH
Opalgyne	MeSH
PMS-Benzydamine	MeSH
Sun benz	MeSH
ratio-Benzydamine	MeSH
Benzydamine hydrochloride	MeSH
Grossmann brand OF benzydamine hydrochloride	MeSH
Innotech brand OF benzydamine hydrochloride	MeSH
Lonol	MeSH
novo Benzydamine	MeSH
Novopharm brand OF benzydamine hydrochloride	MeSH
Ratiopharm brand OF benzydamine hydrochloride	MeSH
Rosalgin	MeSH
United drug brand OF benzydamine hydrochloride	MeSH

Chemical Formula

C₁₉H₂₃N₃O

Average Molecular Weight

309.413

Monoisotopic Molecular Weight

309.184112373

IUPAC Name

{3-[(1-benzyl-1H-indazol-3-yl)oxy]propyl}dimethylamine

Traditional Name

tantum

CAS Registry Number

Not Available

SMILES

CN(C)CCCOC1=NN(CC2=CC=CC=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C19H23N3O/c1-21(2)13-8-14-23-19-17-11-6-7-12-18(17)22(20-19)15-16-9-4-3-5-10-16/h3-7,9-12H,8,13-15H2,1-2H3

InChI Key

CNBGNNVCVSKAQZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indazoles. Indazoles are compounds containing an indazole, which is structurally characterized by a pyrazole fused to a benzene.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrazoles

Sub Class

Indazoles

Direct Parent

Indazoles

Alternative Parents

Substituents

Benzopyrazole
Indazole
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Azole
Pyrazole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Ether
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.78	ALOGPS
logP	3.66	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.56 m³·mol⁻¹	ChemAxon
Polarizability	35.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	202.241	30932474
DeepCCS	[M+Na]+	177.806	30932474
AllCCS	[M+H]+	175.8	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	178.7	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	180.9	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
BENZYDAMINE	CN(C)CCCOC1=NN(CC2=CC=CC=C2)C2=CC=CC=C12	3411.9	Standard polar	33892256
BENZYDAMINE	CN(C)CCCOC1=NN(CC2=CC=CC=C2)C2=CC=CC=C12	2463.4	Standard non polar	33892256
BENZYDAMINE	CN(C)CCCOC1=NN(CC2=CC=CC=C2)C2=CC=CC=C12	2449.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzydamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9220000000-be226c37efcc0d490030	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzydamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 10V, Positive-QTOF	splash10-03di-4059000000-68c288862c826a4bbde9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 20V, Positive-QTOF	splash10-0006-9030000000-b6a400171cb4eab8f9a9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 40V, Positive-QTOF	splash10-0006-9100000000-e87ec195f53e0e686d0d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 10V, Negative-QTOF	splash10-066r-1193000000-08802cf623071d1e0a12	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 20V, Negative-QTOF	splash10-001i-2910000000-2cd9381eac02d19c906e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 40V, Negative-QTOF	splash10-001i-1910000000-97e535700deffb677425	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 10V, Positive-QTOF	splash10-03di-1009000000-f1fd814c343768a7ab9d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 20V, Positive-QTOF	splash10-03dl-9038000000-d2d55f1d72122de60017	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 40V, Positive-QTOF	splash10-0006-9300000000-ec0a3a733e0fbe292044	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 10V, Negative-QTOF	splash10-0a4i-0009000000-c18bba2ef8c410caafc2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 20V, Negative-QTOF	splash10-0a4i-0094000000-6bad4e098b15f9c0b1d9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzydamine 40V, Negative-QTOF	splash10-001i-1930000000-f963470295d4c2e9c6e9	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09084

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzydamine

METLIN ID

Not Available

PubChem Compound

12555

PDB ID

Not Available

ChEBI ID

94563

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Benzydamine (HMDB0249061)

MOL for HMDB0249061 (Benzydamine)

3D MOL for HMDB0249061 (Benzydamine)

3D SDF for HMDB0249061 (Benzydamine)

3D-SDF for HMDB0249061 (Benzydamine)

PDB for HMDB0249061 (Benzydamine)

3D PDB for HMDB0249061 (Benzydamine)

SMILES for HMDB0249061 (Benzydamine)

INCHI for HMDB0249061 (Benzydamine)

Structure for HMDB0249061 (Benzydamine)

3D Structure for HMDB0249061 (Benzydamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra