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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:43 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002227

Secondary Accession Numbers

HMDB02227

Metabolite Identification

Common Name

Capsaicin

Description

Capsaicin is identified as the primary pungent principle in Capsicum fruits. Hot chili peppers that belong to the plant genus Capsicum (family Solanaceae) are among the most heavily consumed spices throughout the world. The capsaicin content of green and red peppers ranges from 0.1 to 1%. Capsaicin evokes numerous biological effects and thus has been the target of extensive., investigations since its initial identification in 1919. One of the most recognized physiological properties of capsaicin is its selective effects on the peripheral part of the sensory nervous system, particularly on the primary afferent neurons. The compound is known to deplete the neurotransmitter of painful impulses known as substance P from the sensory nerve terminals, which provides a rationale for its use as a versatile experimental tool for studying pain mechanisms and also for pharmacotherapy to treat some peripheral painful states, such as rheumatoid arthritis, post-herpetic neuralgia, post-mastectomy pain syndrome and diabetic neuropathy. Considering the frequent consumption of capsaicin as a food additive and its current therapeutic application, correct assessment of any harmful effects of this compound is important from the public health standpoint. Ingestion of large amounts of capsaicin has been reported to cause histopathological and biochemical changes, including erosion of gastric mucosa and hepatic necrosis. However, there are contradictory data on the mutagenicity of capsaicin. A recent epidemiological study conducted in Mexico revealed that consumers of chili pepper were at higher risk for gastric cancer than non-consumers. However, it remains unclear whether capsaicin present in hot chili pepper is a major causative factor in the aetiology of gastric cancer in humans. A growing number of recent studies have focused on anticarcinogenic or antimutagenic phytochemicals, particularly those included in human diet. In summary, capsaicin has dual effects on chemically induced carcinogenesis and mutagenesis. Although a minute amount of capsaicin displays few or no deleterious effects, heavy ingestion of the compound has been associated with necrosis, ulceration and even carcinogenesis. Capsaicin is considered to be metabolized by cytochrome P-450-dependent mixed-function oxidases to reactive species. (PMID: 8621114 ).

Structure

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

HMDB0002227
     RDKit          3D
Capsaicin
 49 49  0  0  0  0  0  0  0  0999 V2000
    6.3184    3.5284   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982    2.2061   -0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5183    1.1310    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712    1.0261   -0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5651   -0.2437   -0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1991   -0.4241   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936   -0.3908   -0.5962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342   -0.3494   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -0.1805   -1.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088   -2.1117   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -2.3430   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661   -1.8458    0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257   -0.4608    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6027    0.3214    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4918   -0.1271   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5659    0.7140   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814    2.1243   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8759    0.0832   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4095   -1.3811    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367   -1.2495    0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921   -0.0701    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6644    0.1492    0.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2889    4.2239    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162    3.8509   -1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222    3.7813   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107    1.8559   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3233   -1.5634   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -1.3380    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792    0.9870   -0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1878   -2.1069    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938   -2.4078   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234   -1.8372   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0251   -3.4216   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3388   -2.4296    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -2.3362    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7538   -0.4410    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909    0.1232    1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212    1.4285    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5320   -1.2008   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4733    0.6362   -2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1978    2.3022    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143    2.6616   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1498    2.6923   -1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0042    0.2634    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7083   -1.0226   -0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6937    0.3730   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9339   -2.3799    0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3147   -2.1887    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2882   -0.6116    0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
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 11 32  1  0
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 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 22 49  1  0
M  END


  Mrv0541 02231218082D          

 22 22  0  0  0  0            999 V2000
    6.3799    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    4.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    3.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 19  1  0  0  0  0
  2 22  1  0  0  0  0
  3 21  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
  9 15  1  0  0  0  0
  9 16  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002227

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+

> <INCHI_KEY>
YKPUWZUDDOIDPM-SOFGYWHQSA-N

> <FORMULA>
C18H27NO3

> <MOLECULAR_WEIGHT>
305.4119

> <EXACT_MASS>
305.199093735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.32071362065211

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.7496695443333334

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.950140339612052

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.928691716239767

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5195533412013454

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
90.31740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
capsaicin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002227
     RDKit          3D
Capsaicin
 49 49  0  0  0  0  0  0  0  0999 V2000
    6.3184    3.5284   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982    2.2061   -0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5183    1.1310    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712    1.0261   -0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5651   -0.2437   -0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1991   -0.4241   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936   -0.3908   -0.5962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342   -0.3494   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -0.1805   -1.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088   -2.1117   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -2.3430   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661   -1.8458    0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257   -0.4608    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6027    0.3214    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4918   -0.1271   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5659    0.7140   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814    2.1243   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8759    0.0832   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4095   -1.3811    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367   -1.2495    0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921   -0.0701    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6644    0.1492    0.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2889    4.2239    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162    3.8509   -1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222    3.7813   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107    1.8559   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3233   -1.5634   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -1.3380    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792    0.9870   -0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1878   -2.1069    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938   -2.4078   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234   -1.8372   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0251   -3.4216   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3388   -2.4296    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -2.3362    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7538   -0.4410    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909    0.1232    1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212    1.4285    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5320   -1.2008   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4733    0.6362   -2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1978    2.3022    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143    2.6616   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1498    2.6923   -1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0042    0.2634    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7083   -1.0226   -0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6937    0.3730   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9339   -2.3799    0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3147   -2.1887    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2882   -0.6116    0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 22 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.909   1.540   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574   7.700   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907   6.160   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.242   1.540   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      11.909  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.909  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.243  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.576  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.577  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.243  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.576   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.577  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.242   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.910  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.243  -8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908   5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.574   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.574   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.241   5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.908   8.470   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   19   22                                                       
CONECT    3   21                                                            
CONECT    4   11   13                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   10                                                       
CONECT    8    6   11                                                       
CONECT    9   12   15   16                                                  
CONECT   10    7   12                                                       
CONECT   11    1    4    8                                                  
CONECT   12    9   10                                                       
CONECT   13    4   14                                                       
CONECT   14   13   17   18                                                  
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17   14   19                                                       
CONECT   18   14   20                                                       
CONECT   19    2   17   21                                                  
CONECT   20   18   21                                                       
CONECT   21    3   19   20                                                  
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0002227
HETATM    1  C1  UNL     1       6.318   3.528  -0.261  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.298   2.206  -0.009  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.518   1.131   0.027  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.171   1.026  -0.156  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.565  -0.244  -0.105  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.199  -0.424  -0.116  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.994  -0.391  -0.596  1.00  0.00           N  
HETATM    8  C6  UNL     1      -0.234  -0.349  -1.087  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.223  -0.181  -1.512  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.409  -2.112  -0.691  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.828  -2.343  -0.481  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.366  -1.846   0.824  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.526  -0.461   1.153  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.603   0.321   0.503  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.492  -0.127  -0.309  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.566   0.714  -0.949  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.581   2.124  -0.502  1.00  0.00           C  
HETATM   18  C15 UNL     1      -6.876   0.083  -0.461  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.409  -1.381   0.135  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.737  -1.250   0.314  1.00  0.00           C  
HETATM   21  C18 UNL     1       6.292  -0.070   0.268  1.00  0.00           C  
HETATM   22  O3  UNL     1       7.664   0.149   0.435  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.289   4.224   0.595  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.716   3.851  -1.123  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.422   3.781  -0.655  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.511   1.856  -0.332  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.323  -1.563  -0.948  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.069  -1.338   0.805  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.179   0.987  -0.924  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.188  -2.107   0.188  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.094  -2.408  -1.600  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.423  -1.837  -1.326  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.025  -3.422  -0.560  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.339  -2.430   1.065  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.664  -2.336   1.594  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.754  -0.441   2.298  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.591   0.123   1.107  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.621   1.428   0.730  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.532  -1.201  -0.562  1.00  0.00           H  
HETATM   40  H18 UNL     1      -5.473   0.636  -2.035  1.00  0.00           H  
HETATM   41  H19 UNL     1      -6.198   2.302   0.390  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.614   2.662  -0.444  1.00  0.00           H  
HETATM   43  H21 UNL     1      -6.150   2.692  -1.314  1.00  0.00           H  
HETATM   44  H22 UNL     1      -7.004   0.263   0.629  1.00  0.00           H  
HETATM   45  H23 UNL     1      -6.708  -1.023  -0.542  1.00  0.00           H  
HETATM   46  H24 UNL     1      -7.694   0.373  -1.101  1.00  0.00           H  
HETATM   47  H25 UNL     1       3.934  -2.380   0.139  1.00  0.00           H  
HETATM   48  H26 UNL     1       6.315  -2.189   0.508  1.00  0.00           H  
HETATM   49  H27 UNL     1       8.288  -0.612   0.588  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6   19   19
CONECT    6    7   27   28
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   36   37
CONECT   14   15   15   38
CONECT   15   16   39
CONECT   16   17   18   40
CONECT   17   41   42   43
CONECT   18   44   45   46
CONECT   19   20   47
CONECT   20   21   21   48
CONECT   21   22
CONECT   22   49
END

HMDB0002227
     RDKit          3D
Capsaicin
 49 49  0  0  0  0  0  0  0  0999 V2000
    6.3184    3.5284   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982    2.2061   -0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5183    1.1310    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712    1.0261   -0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5651   -0.2437   -0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1991   -0.4241   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936   -0.3908   -0.5962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342   -0.3494   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -0.1805   -1.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088   -2.1117   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -2.3430   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661   -1.8458    0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257   -0.4608    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6027    0.3214    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4918   -0.1271   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5659    0.7140   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814    2.1243   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8759    0.0832   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4095   -1.3811    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367   -1.2495    0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921   -0.0701    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6644    0.1492    0.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2889    4.2239    0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162    3.8509   -1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222    3.7813   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107    1.8559   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3233   -1.5634   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -1.3380    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792    0.9870   -0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1878   -2.1069    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938   -2.4078   -1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234   -1.8372   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0251   -3.4216   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3388   -2.4296    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -2.3362    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7538   -0.4410    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909    0.1232    1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212    1.4285    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5320   -1.2008   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4733    0.6362   -2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1978    2.3022    0.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143    2.6616   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1498    2.6923   -1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0042    0.2634    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7083   -1.0226   -0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6937    0.3730   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9339   -2.3799    0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3147   -2.1887    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2882   -0.6116    0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 22 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-8-Methyl-N-vanillyl-6-nonenamide	ChEBI
Isodecenoic acid vanillylamide	ChEBI
trans-8-Methyl-N-vanillyl-6-nonenamide	ChEBI
Zostrix	ChEBI
Isodecenoate vanillylamide	Generator
(e)-8-Methyl-N-vanillyl-6-nonenamide(8CL)	HMDB
(e)8-Methyl-N-vanillyl-6-nonenamide	HMDB
Axsain	HMDB
e-Capsaicin	HMDB
epsilon-Capsaicin	HMDB
Isodecenoate	HMDB
Isodecenoic acid	HMDB
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide	HMDB
Styptysat	HMDB
Transacin	HMDB
Gelcen	HMDB
Link brand OF capsaicin	HMDB
8 Methyl N vanillyl 6 nonenamide	HMDB
Capsicum farmaya	HMDB
Capzasin	HMDB
Flemming brand OF capsaicin	HMDB
8-Methyl-N-vanillyl-6-nonenamide	HMDB
Capsin	HMDB
Katrum	HMDB
Medicis brand OF capsaicin	HMDB
Smaller brand OF capsaicin	HMDB
Thompson brand OF capsaicin	HMDB
Vinas brand OF capsaicin	HMDB
Alacan brand OF capsaicin	HMDB
Antiphlogistine rub a-535 capsaicin	HMDB
Capsaicine	HMDB
Capsidol	HMDB
Carter horner brand OF capsaicin	HMDB
Centrum brand OF capsaicin	HMDB
Elan brand OF capsaicin	HMDB
Zacin	HMDB

Chemical Formula

C₁₈H₂₇NO₃

Average Molecular Weight

305.4119

Monoisotopic Molecular Weight

305.199093735

IUPAC Name

(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

Traditional Name

capsaicin

CAS Registry Number

404-86-4

SMILES

COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1

InChI Identifier

InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+

InChI Key

YKPUWZUDDOIDPM-SOFGYWHQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Fatty amide
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

capsaicinoid (CHEBI:3374 )
Capsaicinoids and derivatives (C06866 )

Ontology

Feces (PMID: 27543620)

Cellular substructure

Extracellular (HMDB: HMDB0002227)
Membrane (HMDB: HMDB0002227)

Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)
Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Process

Not Available

Role

Industrial applicationBiological role

non-narcotic analgesic (HMDB: HMDB0002227)
voltage-gated sodium channel blocker (HMDB: HMDB0002227)
analgesic (HMDB: HMDB0002227)
anaphylactic (HMDB: HMDB0002227)
anesthetic (HMDB: HMDB0002227)
anti aggregant (HMDB: HMDB0002227)
anti arrhythmic (HMDB: HMDB0002227)
anti colonospasmic (HMDB: HMDB0002227)
anti inflammatory (HMDB: HMDB0002227)
anti ischemic (HMDB: HMDB0002227)
anti mastalgic (HMDB: HMDB0002227)
anti neuralgic (HMDB: HMDB0002227)
anti neuritic (HMDB: HMDB0002227)
anti nitrosaminic (HMDB: HMDB0002227)
anti nociceptive (HMDB: HMDB0002227)
Antioxidant (HMDB: HMDB0002227)
anti psoriatic (HMDB: HMDB0002227)
anti septic (HMDB: HMDB0002227)
anti spasmodic (HMDB: HMDB0002227)
anti tachycardic (HMDB: HMDB0002227)
antitumor (HMDB: HMDB0002227)
anti ulcer (HMDB: HMDB0002227)
calcium antagonist (HMDB: HMDB0002227)
cancer preventive (HMDB: HMDB0002227)
carcinogenic (HMDB: HMDB0002227)
cardiotonic (HMDB: HMDB0002227)
catabolic (HMDB: HMDB0002227)
diaphoretic (HMDB: HMDB0002227)
digestive (HMDB: HMDB0002227)
endocrinactive (HMDB: HMDB0002227)
hypothermic (HMDB: HMDB0002227)
irritant (HMDB: HMDB0002227)
neurotoxin (HMDB: HMDB0002227)
pyrogenic (HMDB: HMDB0002227)
repellent (HMDB: HMDB0002227)
respirasensitizer (HMDB: HMDB0002227)
rubefacient (HMDB: HMDB0002227)
sialogogue (HMDB: HMDB0002227)
thermogenic (HMDB: HMDB0002227)

Modulator

Inhibitor

Enzyme inhibitor

5-lipoxygenase inhibitor (HMDB: HMDB0002227)
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (HMDB: HMDB0002227)
cyclooxygenase inhibitor (HMDB: HMDB0002227)
cytochrome-P450 inhibitor (HMDB: HMDB0002227)

Indirect biological role

antioxidant (HMDB: HMDB0002227)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	65 °C	Not Available
Boiling Point	210.00 to 220.00 °C. @ 0.01 mm Hg	The Good Scents Company Information System
Water Solubility	4.41 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.327 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	183.0	30932474
[M+H]+	Not Available	181.643	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000834

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0084 g/L	ALOGPS
logP	3.8	ALOGPS
logP	3.75	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-0.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	36.32 Å³	ChemAxon
Number of Rings	1	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]+	176.189	31661259
DarkChem	[M-H]-	175.031	31661259
DeepCCS	[M+H]+	188.748	30932474
DeepCCS	[M-H]-	186.39	30932474
DeepCCS	[M-2H]-	219.277	30932474
DeepCCS	[M+Na]+	194.841	30932474
AllCCS	[M+H]+	177.3	32859911
AllCCS	[M+H-H2O]+	174.3	32859911
AllCCS	[M+NH4]+	180.1	32859911
AllCCS	[M+Na]+	180.9	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	179.4	32859911
AllCCS	[M+HCOO]-	180.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Capsaicin	COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1	3625.3	Standard polar	33892256
Capsaicin	COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1	2497.8	Standard non polar	33892256
Capsaicin	COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1	2555.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Capsaicin,1TMS,isomer #1	COC1=CC(CNC(=O)CCCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C	2635.9	Semi standard non polar	33892256
Capsaicin,1TMS,isomer #2	COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O	2521.3	Semi standard non polar	33892256
Capsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2552.7	Semi standard non polar	33892256
Capsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2531.4	Standard non polar	33892256
Capsaicin,2TMS,isomer #1	COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2803.1	Standard polar	33892256
Capsaicin,1TBDMS,isomer #1	COC1=CC(CNC(=O)CCCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2879.1	Semi standard non polar	33892256
Capsaicin,1TBDMS,isomer #2	COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2749.9	Semi standard non polar	33892256
Capsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3019.0	Semi standard non polar	33892256
Capsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2927.3	Standard non polar	33892256
Capsaicin,2TBDMS,isomer #1	COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2975.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Capsaicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-052o-9860000000-4151cd60d08276e5122a	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capsaicin GC-MS (1 TMS) - 70eV, Positive	splash10-03mi-9576000000-fb9f159d71790f546865	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capsaicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capsaicin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin LC-ESI-QTOF , negative-QTOF	splash10-014i-0901000000-adba1bb6f254087febe8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin LC-ESI-ITTOF , negative-QTOF	splash10-014i-0900000000-5be0e66854b20d7a5a03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , negative-QTOF	splash10-014i-0900000000-4337ff26dcbd2a77725e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , negative-QTOF	splash10-014i-0900000000-c94a246143850aa73e44	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , negative-QTOF	splash10-014r-0950000000-3d145ef428e054b3e535	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , negative-QTOF	splash10-014r-0950000000-c3ca097a6480ab798ff3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin LC-ESI-QTOF , positive-QTOF	splash10-000i-0900000000-4e8f98d1f848f30117d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-000i-0900000000-58fab2fdd15893ea71e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-000i-0900000000-296a0cb1555da4f1ccd7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-03di-0209000000-a91e6403d5a0c0b67c2e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-03di-0209000000-dd0879d3f4f3a8b022c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-014i-0149000000-d6a9f6e70ae7cd7aec38	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-014i-0149000000-6fcf63c3bf44a4efc5bd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-06sl-0075690000-b562b766019cc7cbd98f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-01x3-0094560000-f354077f4cd51e45b945	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-004i-0002900000-ce1ea9819252343543cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-004i-0002911000-6c37470f794c89a66410	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-000i-0900000000-00619747b8012ce6aa64	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOF	splash10-000i-0900000000-3ca73f5212a7643b45d2	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsaicin 10V, Positive-QTOF	splash10-0udi-0912000000-95e090cebb8f95d7fe89	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsaicin 20V, Positive-QTOF	splash10-0udi-0900000000-6fb8b34936b848190c39	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsaicin 40V, Positive-QTOF	splash10-0f79-4900000000-ade1e8ba842adf972c83	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsaicin 10V, Negative-QTOF	splash10-0udi-0419000000-80bfd538da9be3f08fe0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsaicin 20V, Negative-QTOF	splash10-0udi-0922000000-00b0b7b3e9df2464d425	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsaicin 40V, Negative-QTOF	splash10-0006-7900000000-8b112ae03b8d84d338f3	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06774

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Capsaicin

METLIN ID

Not Available

PubChem Compound

1548943

PDB ID

Not Available

ChEBI ID

3374

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027601

References

Synthesis Reference

Gannett, Peter M.; Nagel, Donald L.; Reilly, Pam J.; Lawson, Terence; Sharpe, Jody; Toth, Bela. Capsaicinoids: their separation, synthesis, and mutagenicity. Journal of Organic Chemistry (1988), 53(5), 1064-71.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Surh YJ, Lee SS: Capsaicin in hot chili pepper: carcinogen, co-carcinogen or anticarcinogen? Food Chem Toxicol. 1996 Mar;34(3):313-6. [PubMed:8621114 ]
Simpson DM, Estanislao L, Brown SJ, Sampson J: An open-label pilot study of high-concentration capsaicin patch in painful HIV neuropathy. J Pain Symptom Manage. 2008 Mar;35(3):299-306. Epub 2007 Oct 23. [PubMed:17959343 ]

Showing metabocard for Capsaicin (HMDB0002227)

MOL for HMDB0002227 (Capsaicin)

3D MOL for HMDB0002227 (Capsaicin)

3D SDF for HMDB0002227 (Capsaicin)

3D-SDF for HMDB0002227 (Capsaicin)

PDB for HMDB0002227 (Capsaicin)

3D PDB for HMDB0002227 (Capsaicin)

SMILES for HMDB0002227 (Capsaicin)

INCHI for HMDB0002227 (Capsaicin)

Structure for HMDB0002227 (Capsaicin)

3D Structure for HMDB0002227 (Capsaicin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra