NP-MRD: Showing NP-Card for L-Tryptophan (NP0001161)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-03 04:16:38 UTC

NP-MRD ID

NP0001161

Natural Product DOI

https://doi.org/10.57994/0741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Tryptophan

Description

Tryptophan (Trp) or L-tryptophan is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tryptophan is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Tryptophan is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tryptophan is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. The requirement for tryptophan and protein decreases with age. The minimum daily requirement for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ. A cup of low-fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://Www.Dcnutrition.Com). Tryptophan is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Tryptophan is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of conditions or diseases that are characterized by tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn diets or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia. Hartnup's disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnup's disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnup's disease. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin by the pineal gland, which promotes sleep. Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed that consumption of tryptophan or 5-HTP may improve depression symptoms by increasing the level of serotonin in the brain. Tryptophan is sold over the counter in the United States (after being banned to varying extents between 1989 and 2005) and the United Kingdom as a dietary supplement for use as an antidepressant, anxiolytic, and sleep aid. It is also marketed as a prescription drug in some European countries for the treatment of major depression. There is evidence that blood tryptophan levels are unlikely to be altered by changing the diet, but consuming purified tryptophan increases the serotonin level in the brain, whereas eating foods containing tryptophan does not. This is because the transport system that brings tryptophan across the blood–brain barrier also transports other amino acids which are contained in protein food sources. Under certain situations, tryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of tryptophan can be found in glutaric aciduria type I (glutaric acidemia type I or GA1). GA1 is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine, and tryptophan due to a deficiency of mitochondrial glutaryl-CoA dehydrogenase (EC 1.3.99.7, GCDH). Excessive levels of their intermediate breakdown products (e.G. Glutaric acid, glutaryl-CoA, 3-hydroxyglutaric acid, glutaconic acid) can accumulate and cause damage to the brain (and also other organs), but particularly the basal ganglia. Babies with glutaric acidemia type I are often born with unusually large heads (macrocephaly). Other symptoms include spasticity (increased muscle tone/stiffness) and dystonia (involuntary muscle contractions resulting in abnormal movement or posture), but many affected individuals are asymptomatic. High levels of tryptophan have also been implicated in eosinophilia-myalgia syndrome (EMS), an incurable and sometimes fatal flu-like neurological condition linked to the ingestion of large amounts of L-tryptophan. The risk of developing EMS increases with larger doses of tryptophan and increasing age. Some research suggests that certain genetic polymorphisms may be related to the development of EMS. The presence of eosinophilia is a core feature of EMS, along with unusually severe myalgia (muscle pain). It is thought that both tryptophan and certain unidentified tryptophan contaminants may contribute to EMS (PMID: 1763543 ). It has also been suggested that excessive tryptophan or elevation of its metabolites could play a role in amplifying some of the pathological features of EMS (PMID: 10721094 ). This pathological damage is further augmented by metabolites of the kynurenine pathway (a tryptophan degradation pathway).

Structure

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


  Mrv1652309042000142D          

 15 16  0  0  1  0            999 V2000
    0.0032   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -1.2545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025   -0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1095   -0.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -0.2625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4321   -1.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1

> <INCHI_KEY>
QIVBCDIJIAJPQS-VIFPVBQESA-N

> <FORMULA>
C11H12N2O2

> <MOLECULAR_WEIGHT>
204.2252

> <EXACT_MASS>
204.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.047414013171778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-1.0854569138833579

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.1565885064574

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5439286383469866

> <JCHEM_PKA_STRONGEST_BASIC>
9.396082567807317

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
56.20280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-tryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       0.006  -0.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.155  -2.022   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.661  -2.342   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.431  -1.008   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.401   0.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.877   1.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.938  -0.688   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.414   0.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.383   1.921   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.007   1.820   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.007   0.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.341  -0.490   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.673  -0.490   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.673  -2.030   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.340   0.280   0.000  0.00  0.00           C+0
CONECT    1    2    5   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    9                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8                                                       
CONECT   10   11                                                            
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    1                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0000929
HETATM    1  N1  UNL     1       2.923  -1.892   0.959  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.034  -0.913   0.356  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.836  -0.812   1.287  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.177   0.141   0.832  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.424   1.396   1.308  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.442   1.968   0.630  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.853   1.075  -0.288  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.857   1.161  -1.231  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.088   0.078  -2.082  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.333  -1.067  -1.991  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.342  -1.123  -1.044  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.086  -0.064  -0.183  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.747   0.367   0.262  1.00  0.00           C  
HETATM   14  O1  UNL     1       3.918   0.458   0.664  1.00  0.00           O  
HETATM   15  O2  UNL     1       2.110   1.463  -0.275  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.926  -1.608   0.900  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.724  -2.038   1.978  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.715  -1.262  -0.655  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.245  -0.567   2.294  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.413  -1.859   1.328  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.110   1.869   2.106  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.865   2.909   0.751  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.464   2.063  -1.313  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.891   0.199  -2.804  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.552  -1.877  -2.675  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.758  -2.045  -0.994  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.430   1.981  -1.084  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3   13   18
CONECT    3    4   19   20
CONECT    4    5    5   12
CONECT    5    6   21
CONECT    6    7   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   13   14   14   15
CONECT   15   27
END

View in JSmol

Synonyms

Value	Source
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid	ChEBI
(S)-alpha-Amino-1H-indole-3-propanoic acid	ChEBI
(S)-alpha-Amino-beta-(3-indolyl)-propionic acid	ChEBI
(S)-Tryptophan	ChEBI
L-(-)-Tryptophan	ChEBI
L-beta-3-Indolylalanine	ChEBI
Trp	ChEBI
Tryptophan	ChEBI
W	ChEBI
(2S)-2-Amino-3-(1H-indol-3-yl)propanoate	Generator
(S)-a-Amino-1H-indole-3-propanoate	Generator
(S)-a-Amino-1H-indole-3-propanoic acid	Generator
(S)-alpha-Amino-1H-indole-3-propanoate	Generator
(S)-Α-amino-1H-indole-3-propanoate	Generator
(S)-Α-amino-1H-indole-3-propanoic acid	Generator
(S)-a-Amino-b-(3-indolyl)-propionate	Generator
(S)-a-Amino-b-(3-indolyl)-propionic acid	Generator
(S)-alpha-Amino-beta-(3-indolyl)-propionate	Generator
(S)-Α-amino-β-(3-indolyl)-propionate	Generator
(S)-Α-amino-β-(3-indolyl)-propionic acid	Generator
L-b-3-Indolylalanine	Generator
L-Β-3-indolylalanine	Generator
(-)-Tryptophan	HMDB
(L)-Tryptophan	HMDB
(S)-1H-Indole-3-alanine	HMDB
(S)-2-Amino-3-(3-indolyl)propionic acid	HMDB
(S)-a-Amino-b-indolepropionate	HMDB
(S)-a-Amino-b-indolepropionic acid	HMDB
(S)-a-Aminoindole-3-propionate	HMDB
(S)-a-Aminoindole-3-propionic acid	HMDB
(S)-alpha-Amino-beta-indolepropionate	HMDB
(S)-alpha-Amino-beta-indolepropionic acid	HMDB
(S)-alpha-Aminoindole-3-propionate	HMDB
(S)-alpha-Aminoindole-3-propionic acid	HMDB
1-beta-3-Indolylalanine	HMDB
1beta-3-Indolylalanine	HMDB
1H-Indole-3-alanine	HMDB
2-Amino-3-indolylpropanoate	HMDB
2-Amino-3-indolylpropanoic acid	HMDB
3-(1H-indol-3-yl)-L-Alanine	HMDB
3-indol-3-Ylalanine	HMDB
Alpha'-amino-3-indolepropionic acid	HMDB
alpha-Aminoindole-3-propionic acid	HMDB
Ardeytropin	HMDB
H-TRP-OH	HMDB
Indole-3-alanine	HMDB
Kalma	HMDB
L-alpha-Amino-3-indolepropionic acid	HMDB
L-alpha-Aminoindole-3-propionic acid	HMDB
L-Tryptofan	HMDB
L-Tryptophane	HMDB
Lopac-T-0254	HMDB
Lyphan	HMDB
Optimax	HMDB
Pacitron	HMDB
Sedanoct	HMDB
Triptofano	HMDB
Trofan	HMDB
Tryptacin	HMDB
Tryptan	HMDB
Tryptophane	HMDB
Tryptophanum	HMDB
Ardeydorm	HMDB
L Tryptophan	HMDB
L-Tryptophan-ratiopharm	HMDB
Merck brand OF tryptophan	HMDB
Niddapharm brand OF tryptophan	HMDB
ICN brand OF tryptophan	HMDB
Levotryptophan	HMDB
PMS Tryptophan	HMDB
PMS-Tryptophan	HMDB
Ratiopharm brand OF tryptophan	HMDB
Esparma brand OF tryptophan	HMDB
Ratio-tryptophan	HMDB
L Tryptophan ratiopharm	HMDB
Naturruhe	HMDB
Tryptophan metabolism alterations	HMDB
Ardeypharm brand OF tryptophan	HMDB
Kalma brand OF tryptophan	HMDB
Pharmascience brand OF tryptophan	HMDB
Upsher-smith brand OF tryptophan	HMDB
Ratio tryptophan	HMDB

Chemical Formula

C₁₁H₁₂N₂O₂

Average Mass

204.2252 Da

Monoisotopic Mass

204.08988 Da

IUPAC Name

(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

Traditional Name

L-tryptophan

CAS Registry Number

73-22-3

SMILES

N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

InChI Identifier

InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1

InChI Key

QIVBCDIJIAJPQS-VIFPVBQESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-02-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	yupingfu424@163.com	Not Available	Not Available	2023-07-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	yupingfu424@163.com	Not Available	Not Available	2023-07-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	yupingfu424@163.com	Not Available	Not Available	2023-07-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	yupingfu424@163.com	Not Available	Not Available	2023-07-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	yupingfu424@163.com	Not Available	Not Available	2023-07-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	yupingfu424@163.com	Not Available	Not Available	2023-07-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-08-07	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Abramis brama	FooDB	USDA
Acipenser	FooDB	USDA
Acipenseridae	FooDB	USDA
Actinidia chinensis	FooDB	USDA
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	USDA
Allium ampeloprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium ascalonicum	FooDB	USDA
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium cepa L.	FooDB	USDA
Allium chinense	LOTUS Database	35616633
Allium fistulosum	FooDB	USDA
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium schoenoprasum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium tuberosum	FooDB	USDA
Alosa sapidissima	FooDB	USDA
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Amaranthus spinosus	LOTUS Database	35616633
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ananas comosus	FooDB	USDA
Anarhichas lupus	FooDB	USDA
Anatidae	FooDB	USDA
Anethum graveolens	FooDB	USDA
Angelica keiskei	FooDB	FooDB
Anguilla	FooDB	USDA
Anguilliformes	FooDB	USDA
Annona cherimola	FooDB	USDA
Annona muricata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Annona reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Annona squamosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anoplopoma fimbria	FooDB	USDA
Anthriscus cerefolium	FooDB	FooDB
Antirrhinum majus	KNApSAcK Database	22123792
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens var. dulce	FooDB	USDA
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Aplodinotus grunniens	FooDB	USDA
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Archosargus probatocephalus	FooDB	USDA
Arctium lappa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Armoracia rusticana	FooDB	FooDB
Artemia salina	LOTUS Database	35616633
Artemisia absinthium	LOTUS Database	35616633
Artemisia armeniaca	LOTUS Database	35616633
Artemisia dracunculus	FooDB	FooDB
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artocarpus heterophyllus	FooDB	USDA
Ascaris lumbricoides	LOTUS Database	35616633
Asparagus officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Aspergillus clavatus	Fungi	KNApSAcK
Aspergillus fischeri	Fungi	KNApSAcK
Aspergillus fumigatus	Fungi	KNApSAcK
Astacidea	FooDB	USDA
Atractylodes lancea	LOTUS Database	35616633
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Averrhoa carambola	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Basella alba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Benincasa hispida	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Bertholletia excelsa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Beta vulgaris	FooDB	USDA
Beta vulgaris ssp. cicla	FooDB	USDA
Bison bison	FooDB	USDA
Bivalvia	FooDB	USDA
Bombyx mori	LOTUS Database	35616633
Borago officinalis	FooDB	FooDB
Bos taurus	FooDB	DTU Food
Brachyura	FooDB	USDA
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus ssp. rapifera	Plant	KNApSAcK
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	USDA
Brassica oleracea var. botrytis	FooDB	USDA
Brassica oleracea var. capitata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gemmifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. gongylodes	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. italica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Brassica oleracea var. sabauda	FooDB	USDA
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	USDA
Brassica rapa ssp. chinensis	FooDB	USDA
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	USDA
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	USDA
Brosme brosme	FooDB	USDA
Bubalus bubalis	FooDB	USDA
Buccinidae	FooDB	USDA
Bupleurum chinense	LOTUS Database	35616633
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Callinectes sapidus	FooDB	USDA
Canarium ovatum	FooDB	USDA
Cancer magister	FooDB	USDA
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capra aegagrus hircus	FooDB	USDA
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Caridea	FooDB	USDA
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Carya	FooDB	USDA
Carya illinoinensis	FooDB	USDA
Castanea	FooDB	USDA
Castanea crenata	FooDB	USDA
Castanea mollissima	FooDB	USDA
Castanea sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Catostomus commersonii	FooDB	USDA
Ceratonia siliqua	FooDB	USDA
Cervidae	FooDB	USDA
Cervus canadensis	FooDB	USDA
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chanos chanos	FooDB	USDA
Chenopodium album	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chenopodium quinoa	FooDB	USDA
Chionoecetes opilio	FooDB	USDA
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cichlidae	FooDB	USDA
Cichorium endivia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cichorium intybus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum	FooDB	USDA
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Citrullus lanatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus latifolia	FooDB	USDA
Citrus limon	FooDB	FooDB
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	USDA
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cliona celata	LOTUS Database	35616633
Clupea harengus harengus	FooDB	USDA
Clupea pallasii	FooDB	USDA
Cocos nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea arabica L.	FooDB	DTU Food
Coffea canephora	FooDB	DTU Food
Colocasia esculenta	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Columba	FooDB	USDA
Columbidae	FooDB	USDA
Corchorus olitorius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coregonus	FooDB	USDA
Coregonus artedi	FooDB	USDA
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Corylus	FooDB	USDA
Corylus avellana	FooDB	USDA
Crassostrea gigas	FooDB	USDA
Crassostrea virginica	FooDB	USDA
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Ctenodiscus crispatus	LOTUS Database	35616633
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita maxima	FooDB	DTU Food
Cucurbita moschata	FooDB	USDA
Cuminum cyminum	FooDB	FooDB
Curcuma domestica	KNApSAcK Database	22123792
Curcuma longa	FooDB	USDA
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Cynomorium songaricum	LOTUS Database	35616633
Cyprinus carpio	FooDB	USDA
Daphnia pulex	LOTUS Database	35616633
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Davallia mariesii	LOTUS Database	35616633
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	USDA
Dioscorea pentaphylla	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Diospyros	FooDB	USDA
Diospyros kaki	FooDB	USDA
Diospyros virginiana	FooDB	USDA
Dromaius novaehollandiae	FooDB	USDA
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	USDA
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Engraulidae	FooDB	USDA
Engraulis encrasicolus	FooDB	USDA
Epinephelus	FooDB	USDA
Equisetum debile	KNApSAcK Database	22123792
Equisetum ramosissimum	LOTUS Database	35616633
Equisetum ramosissimum subsp. debile	Plant	KNApSAcK
Equus caballus	FooDB	USDA
Eragrostis tef	FooDB	USDA
Eriobotrya japonica	FooDB	USDA
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Ervatamia coronaria	LOTUS Database	35616633
Esox lucius	FooDB	USDA
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	USDA
Feijoa sellowiana	FooDB	USDA
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Fragaria chiloensis	LOTUS Database	35616633
Fragaria x ananassa	FooDB	FooDB
Gadiformes	FooDB	USDA
Gadus	FooDB	USDA
Gadus macrocephalus	FooDB	USDA
Gadus morhua	FooDB	USDA
Garcinia mangostana	FooDB	FooDB
Gaylussacia baccata	FooDB	FooDB
Geranium pratense	LOTUS Database	35616633
Geranium pratense subsp.finitimum (Woronow) Knuth	KNApSAcK Database	22123792
Ginkgo biloba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glehnia littoralis	LOTUS Database	35616633
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium	FooDB	USDA
Grifola frondosa	FooDB	USDA
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus tuberosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hibiscus sabbariffa	FooDB	FooDB
Hippoglossus	FooDB	USDA
Hippoglossus hippoglossus	FooDB	USDA
Hippoglossus stenolepis	FooDB	USDA
Hippophae rhamnoides	FooDB	FooDB
Homarus americanus	FooDB	USDA
Homo sapiens	LOTUS Database	35616633
Hoplostethus atlanticus	FooDB	USDA
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hypholoma fasciculare	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	FooDB
Ictalurus punctatus	FooDB	USDA
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans	FooDB	USDA
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans nigra L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juglans regia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Katsuwonus pelamis	FooDB	USDA
Lablab purpureus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lactuca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lagenaria siceraria	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Laminaria	FooDB	USDA
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Leiostomus xanthurus	FooDB	USDA
Lens culinaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lentinus edodes	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lepidium sativum	FooDB	FooDB
Lepomis gibbosus	FooDB	USDA
Leporidae	FooDB	USDA
Leptasterias polaris	LOTUS Database	35616633
Lethasterias nanimensis	LOTUS Database	35616633
Levisticum officinale	FooDB	FooDB
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Litchi chinensis	FooDB	FooDB
Lophius piscatorius	FooDB	USDA
Lopholatilus chamaeleonticeps	FooDB	USDA
Lota lota	FooDB	USDA
Luffa aegyptiaca	FooDB	FooDB
Luffariella geometrica	-	KNApSAcK
Lupinus	FooDB	USDA
Lupinus albus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lutjanidae	FooDB	USDA
Macadamia	FooDB	USDA
Macadamia tetraphylla	FooDB	USDA
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Manihot esculenta	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Manilkara zapota	FooDB	USDA
Maranta arundinacea	FooDB	USDA
Marchantia polymorpha	LOTUS Database	35616633
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	FooDB
Meleagris gallopavo	FooDB	USDA
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Merlangius merlangus	FooDB	USDA
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Micropogonias undulatus	FooDB	USDA
Microstomus kitt	FooDB	USDA
Mimosa pudica	LOTUS Database	35616633
Mirabilis jalpa	KNApSAcK Database	22123792
Molva molva	FooDB	USDA
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Morone saxatilis	FooDB	USDA
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mugil cephalus	FooDB	USDA
Musa acuminata	FooDB	USDA
Musa x paradisiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mycoplasmopsis bovis	LOTUS Database	35616633
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Mytilidae	FooDB	USDA
Mytilus edulis	FooDB	USDA
Nelumbo	FooDB	USDA
Nelumbo nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Nephelium lappaceum	FooDB	FooDB
Nephropidae	FooDB	USDA
Neptunea antiqua	LOTUS Database	35616633
Numida meleagris	FooDB	USDA
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Octopus vulgaris	FooDB	USDA
Oenothera biennis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Olea europaea	FooDB	FooDB
Oncorhynchus gorbuscha	FooDB	USDA
Oncorhynchus keta	FooDB	USDA
Oncorhynchus kisutch	FooDB	USDA
Oncorhynchus mykiss	FooDB	USDA
Oncorhynchus nerka	FooDB	USDA
Oncorhynchus tshawytscha	FooDB	USDA
Onobrychis viciifolia	LOTUS Database	35616633
Ophiodon elongatus	FooDB	USDA
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	USDA
Opuntia ficus-indica	LOTUS Database	35616633
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	USDA
Origanum X majoricum	FooDB	USDA
Oryctolagus	FooDB	USDA
Oryza rufipogon	FooDB	USDA
Oryza sativa	FooDB	USDA
Osmeridae	FooDB	USDA
Osmerus mordax	FooDB	USDA
Pachyrhizus erosus	FooDB	FooDB
Palinuridae	FooDB	USDA
Panax ginseng	FooDB	FooDB
Panax notoginseng	LOTUS Database	35616633
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	USDA
Paralithodes camtschaticus	FooDB	USDA
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pectinidae	FooDB	USDA
Pediomelum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Penicillium aethiopicum	Fungi	KNApSAcK
Pennisetum americanum	LOTUS Database	35616633
Peprilus triacanthus	FooDB	USDA
Percoidei	FooDB	USDA
Perideridia oregana	FooDB	FooDB
Periplaneta americana	LOTUS Database	35616633
Persea americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	USDA
Peucedanum japonicum	LOTUS Database	35616633
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phasianidae	FooDB	USDA
Phasianus colchicus	FooDB	USDA
Phoenix dactylifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	USDA
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	USDA
Pinus edulis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pinus ponderosa	LOTUS Database	35616633
Piper kadsura	LOTUS Database	35616633
Piper nigrum L.	FooDB	USDA
Pistacia vera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pleuronectiformes	FooDB	USDA
Pleurotus ostreatus	FooDB	USDA
Plumbago zeylanica	KNApSAcK Database	22123792
Pollachius	FooDB	USDA
Pollachius pollachius	FooDB	USDA
Polygonum alpinum	FooDB	FooDB
Pomatomus saltatrix	FooDB	USDA
Populus tremula	LOTUS Database	35616633
Portulaca oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pouteria sapota	FooDB	USDA
Pratia nummularia	KNApSAcK Database	22123792
Prosopis juliflora	LOTUS Database	35616633
Prosopis juliflora (Sw.) DC.	KNApSAcK Database	22123792
Prunus armeniaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica var. nucipersica	FooDB	USDA
Prunus persica var. persica	FooDB	USDA
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Pseudo-nitzschia multistriata	LOTUS Database	35616633
Psidium cattleianum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psidium guajava	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psophocarpus tetragonolobus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Punica granatum	FooDB	FooDB
Pyrus communis	FooDB	USDA
Pyrus pyrifolia	FooDB	USDA
Quercus	FooDB	USDA
Raphanus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Raphanus sativus var. longipinnatus	FooDB	USDA
Raphanus sativus var. sativus	FooDB	FooDB
Reinhardtius hippoglossoides	FooDB	USDA
Rheum rhabarbarum	FooDB	FooDB
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ripariosida hermaphrodita	LOTUS Database	35616633
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Sagittaria sagittifolia	LOTUS Database	35616633
Salix pulchra	FooDB	FooDB
Salmo salar	FooDB	USDA
Salmo trutta forma trutta	FooDB	USDA
Salmonidae	FooDB	USDA
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	USDA
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Scomberomorus cavalla	FooDB	USDA
Scomberomorus maculatus	FooDB	USDA
Scophthalmus maximus	FooDB	USDA
Scorzonera hispanica	FooDB	FooDB
Scrophularia cryptophila	LOTUS Database	35616633
Sebastes	FooDB	USDA
Sebastes alutus	FooDB	USDA
Secale cereale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sechium edule	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sepiidae	FooDB	USDA
Seriola lalandi	FooDB	USDA
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sesbania bispinosa	FooDB	USDA
Siluriformes	FooDB	USDA
Sinapis alba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sisymbrium	FooDB	FooDB
Smallanthus sonchifolius	LOTUS Database	35616633
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum melongena	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Soleidae	FooDB	USDA
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	USDA
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Spirulina	FooDB	USDA
Squaliformes	FooDB	USDA
Stenodus leucichthys	FooDB	USDA
Stenotomus chrysops	FooDB	USDA
Stratiotes aloides	LOTUS Database	35616633
Streptomyces albidoflavus	LOTUS Database	35616633
Streptomyces venezuelae	LOTUS Database	35616633
Struthio camelus	FooDB	USDA
Sus scrofa	FooDB	USDA
Sus scrofa domestica	FooDB	USDA
Syzygium aromaticum	FooDB	USDA
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Taraxacum officinale	FooDB	FooDB
Tecoma stans	LOTUS Database	35616633
Telekia speciosa	LOTUS Database	35616633
Tetragonia tetragonioides	FooDB	FooDB
Teuthida	FooDB	USDA
Thalassiosira pseudonana	LOTUS Database	35616633
Thelesperma	FooDB	FooDB
Thunnus albacares	FooDB	USDA
Thunnus thynnus	FooDB	USDA
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Trachinotus carolinus	FooDB	USDA
Trachurus symmetricus	FooDB	USDA
Tragopogon porrifolius	FooDB	FooDB
Treculia africana	LOTUS Database	35616633
Trifolium pratense L.	KNApSAcK Database	22123792
Trifolium repens	Plant	KNApSAcK
Trifolium repens L.	KNApSAcK Database	22123792
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trisopterus esmarkii	FooDB	USDA
Triticum	FooDB	USDA
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum durum	FooDB	USDA
Triticum spelta	FooDB	USDA
Triticum turanicum	FooDB	USDA
Trypanosoma brucei	LOTUS Database	35616633
Typha angustifolia	FooDB	FooDB
Ulmus thomasii	LOTUS Database	35616633
Undaria pinnatifida	FooDB	USDA
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium deliciosum	FooDB	FooDB
Vaccinium dunalianum	LOTUS Database	35616633
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Valerianella locusta	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vicia sativa	LOTUS Database	35616633
Vigna aconitifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna angularis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna mungo	FooDB	USDA
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	USDA
Vigna unguiculata ssp. cylindrica	FooDB	USDA
Vigna unguiculata ssp. unguiculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna unguiculata var. sesquipedalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Virola surinamensis	FooDB	USDA
Vitellaria paradoxa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitis	FooDB	USDA
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Xanthosoma sagittifolium	FooDB	FooDB
Xiphias gladius	FooDB	USDA
Youngia japonica	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zizania	FooDB	USDA
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB
Zoarces americanus	FooDB	USDA
Zyzzya fuliginosa	-	KNApSAcK

Species Where Detected

Species Name	Source	Reference
Escherichia coli K12	KNApSAcK Database	22123792
Homo sapiens (Serum)	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792
Pleurocybella porrigens	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
3-alkylindole
Indole
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:16828 )
L-alpha-amino acid (CHEBI:16828 )
tryptophan (CHEBI:16828 )
erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:16828 )
Common amino acids (C00078 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	230 °C	Not Available
Boiling Point	269.00 to 270.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	13.4 mg/mL at 25 °C	Yalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP	-1.06	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.2 m³·mol⁻¹	ChemAxon
Polarizability	21.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000929

DrugBank ID

DB00150

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16828

Good Scents ID

rw1027851

References

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
Buczko W, Cylwik D, Stokowska W: [Metabolism of tryptophan via the kynurenine pathway in saliva]. Postepy Hig Med Dosw (Online). 2005;59:283-9. [PubMed:15995595 ]
Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. [PubMed:1422788 ]
Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. [PubMed:2580417 ]
Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. [PubMed:2472426 ]
Guchhait RB, Janson C, Price WH: Validity of plasma factor in schizophrenia as measured by tryptophan uptake. Biol Psychiatry. 1975 Jun;10(3):303-14. [PubMed:49200 ]
Kennedy JS, Gwirtsman HE, Schmidt DE, Johnson BW, Fielstein E, Salomon RM, Shiavi RG, Ebert MH, Parris WC, Loosen PT: Serial cerebrospinal fluid tryptophan and 5-hydroxy indoleacetic acid concentrations in healthy human subjects. Life Sci. 2002 Aug 23;71(14):1703-15. [PubMed:12137916 ]
Bender KI, Lutsevich NF, Lutsevich AN, Kupchikov VV: [Endogenous metabolites as modulators of the transport of drugs by serum albumin]. Farmakol Toksikol. 1990 May-Jun;53(3):72-80. [PubMed:2201566 ]
Heiman-Patterson TD, Bird SJ, Parry GJ, Varga J, Shy ME, Culligan NW, Edelsohn L, Tatarian GT, Heyes MP, Garcia CA, et al.: Peripheral neuropathy associated with eosinophilia-myalgia syndrome. Ann Neurol. 1990 Oct;28(4):522-8. [PubMed:2174666 ]
Talbert AM, Tranter GE, Holmes E, Francis PL: Determination of drug-plasma protein binding kinetics and equilibria by chromatographic profiling: exemplification of the method using L-tryptophan and albumin. Anal Chem. 2002 Jan 15;74(2):446-52. [PubMed:11811421 ]
Dunner DL, Heiber S, Perel JM: The effect of L-tryptophan administration on the concentration of probenecid in plasma and cerebrospinal fluid in patients. Psychopharmacology (Berl). 1977 Aug 16;53(3):305-8. [PubMed:408860 ]
George CF, Millar TW, Hanly PJ, Kryger MH: The effect of L-tryptophan on daytime sleep latency in normals: correlation with blood levels. Sleep. 1989 Aug;12(4):345-53. [PubMed:2669092 ]
Gutsche B, Grun C, Scheutzow D, Herderich M: Tryptophan glycoconjugates in food and human urine. Biochem J. 1999 Oct 1;343 Pt 1:11-9. [PubMed:10493906 ]
Milburn DS, Myers CW: Tryptophan toxicity: a pharmacoepidemiologic review of eosinophilia-myalgia syndrome. DICP. 1991 Nov;25(11):1259-62. [PubMed:1763543 ]
Gross B, Ronen N, Honigman S, Livne E: Tryptophan toxicity--time and dose response in rats. Adv Exp Med Biol. 1999;467:507-16. [PubMed:10721094 ]
Guo L, Schurink B, Roos E, Nossent EJ, Duitman JW, Vlaar AP, van der Valk P, Vaz FM, Yeh SR, Geeraerts Z, Dijkhuis A, van Vught L, Bugiani M, Lutter R: Indoleamine 2,3-dioxygenase (IDO)-1 and IDO-2 activity and severe course of COVID-19. J Pathol. 2022 Mar;256(3):256-261. doi: 10.1002/path.5842. Epub 2022 Jan 10. [PubMed:34859884 ]

Showing NP-Card for L-Tryptophan (NP0001161)

MOL for NP0001161 (L-Tryptophan)

3D MOL for NP0001161 (L-Tryptophan)

3D SDF for NP0001161 (L-Tryptophan)

3D-SDF for NP0001161 (L-Tryptophan)

PDB for NP0001161 (L-Tryptophan)

3D PDB for NP0001161 (L-Tryptophan)

SMILES for NP0001161 (L-Tryptophan)

INCHI for NP0001161 (L-Tryptophan)

Structure for NP0001161 (L-Tryptophan)

3D Structure for NP0001161 (L-Tryptophan)