Showing metabocard for L-Tryptophan (MMDBc0000170)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:38:26 UTC
Update Date2022-08-30 23:59:41 UTC
Metabolite IDMMDBc0000170
Metabolite Identification
Common NameL-Tryptophan
DescriptionTryptophan is an essential amino acid that 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 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. 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. 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 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. 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe2d5e6efa0>


  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
Download

3D MOL for #<Metabolite:0x00007fe2d5e6efa0>

HMDB0000929
     RDKit          3D
L-Tryptophan
 27 28  0  0  0  0  0  0  0  0999 V2000
    2.9229   -1.8923    0.9590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0337   -0.9132    0.3555 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8356   -0.8118    1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767    0.1406    0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237    1.3963    1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    1.9677    0.6301 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8532    1.0751   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    1.1611   -1.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0884    0.0777   -2.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329   -1.0673   -1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417   -1.1227   -1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -0.0636   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    0.3671    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    0.4580    0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097    1.4627   -0.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259   -1.6078    0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239   -2.0377    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -1.2624   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452   -0.5671    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4132   -1.8595    1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101    1.8689    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    2.9092    0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    2.0627   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.1991   -2.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.8770   -2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -2.0454   -0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.9815   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 12  4  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  6
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 15 27  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fe2d5e6efa0>


  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>
MMDBc0000170

> <DATABASE_NAME>
MIME

> <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

$$$$
Download

3D-SDF for #<Metabolite:0x00007fe2d5e6efa0>

HMDB0000929
     RDKit          3D
L-Tryptophan
 27 28  0  0  0  0  0  0  0  0999 V2000
    2.9229   -1.8923    0.9590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0337   -0.9132    0.3555 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8356   -0.8118    1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767    0.1406    0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237    1.3963    1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    1.9677    0.6301 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8532    1.0751   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    1.1611   -1.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0884    0.0777   -2.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329   -1.0673   -1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417   -1.1227   -1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -0.0636   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    0.3671    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    0.4580    0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097    1.4627   -0.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259   -1.6078    0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239   -2.0377    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -1.2624   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452   -0.5671    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4132   -1.8595    1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101    1.8689    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    2.9092    0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    2.0627   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.1991   -2.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.8770   -2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -2.0454   -0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.9815   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 12  4  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  6
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 15 27  1  0
M  END
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PDB for #<Metabolite:0x00007fe2d5e6efa0>

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
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3D PDB for #<Metabolite:0x00007fe2d5e6efa0>

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
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SMILES for #<Metabolite:0x00007fe2d5e6efa0>

N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
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INCHI for #<Metabolite:0x00007fe2d5e6efa0>

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
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Synonyms
ValueSource
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acidChEBI
(S)-alpha-Amino-1H-indole-3-propanoic acidChEBI
(S)-alpha-Amino-beta-(3-indolyl)-propionic acidChEBI
(S)-TryptophanChEBI
L-(-)-TryptophanChEBI
L-beta-3-IndolylalanineChEBI
TrpChEBI
TryptophanChEBI
WChEBI
(2S)-2-Amino-3-(1H-indol-3-yl)propanoateGenerator
(S)-a-Amino-1H-indole-3-propanoateGenerator
(S)-a-Amino-1H-indole-3-propanoic acidGenerator
(S)-alpha-Amino-1H-indole-3-propanoateGenerator
(S)-Α-amino-1H-indole-3-propanoateGenerator
(S)-Α-amino-1H-indole-3-propanoic acidGenerator
(S)-a-Amino-b-(3-indolyl)-propionateGenerator
(S)-a-Amino-b-(3-indolyl)-propionic acidGenerator
(S)-alpha-Amino-beta-(3-indolyl)-propionateGenerator
(S)-Α-amino-β-(3-indolyl)-propionateGenerator
(S)-Α-amino-β-(3-indolyl)-propionic acidGenerator
L-b-3-IndolylalanineGenerator
L-Β-3-indolylalanineGenerator
(-)-TryptophanHMDB
(L)-TryptophanHMDB
(S)-1H-Indole-3-alanineHMDB
(S)-2-Amino-3-(3-indolyl)propionic acidHMDB
(S)-a-Amino-b-indolepropionateHMDB
(S)-a-Amino-b-indolepropionic acidHMDB
(S)-a-Aminoindole-3-propionateHMDB
(S)-a-Aminoindole-3-propionic acidHMDB
(S)-alpha-Amino-beta-indolepropionateHMDB
(S)-alpha-Amino-beta-indolepropionic acidHMDB
(S)-alpha-Aminoindole-3-propionateHMDB
(S)-alpha-Aminoindole-3-propionic acidHMDB
1-beta-3-IndolylalanineHMDB
1beta-3-IndolylalanineHMDB
1H-Indole-3-alanineHMDB
2-Amino-3-indolylpropanoateHMDB
2-Amino-3-indolylpropanoic acidHMDB
3-(1H-indol-3-yl)-L-AlanineHMDB
3-indol-3-YlalanineHMDB
Alpha'-amino-3-indolepropionic acidHMDB
alpha-Aminoindole-3-propionic acidHMDB
ArdeytropinHMDB
H-TRP-OHHMDB
Indole-3-alanineHMDB
KalmaHMDB
L-alpha-Amino-3-indolepropionic acidHMDB
L-alpha-Aminoindole-3-propionic acidHMDB
L-TryptofanHMDB
L-TryptophaneHMDB
Lopac-T-0254HMDB
LyphanHMDB
OptimaxHMDB
PacitronHMDB
SedanoctHMDB
TriptofanoHMDB
TrofanHMDB
TryptacinHMDB
TryptanHMDB
TryptophaneHMDB
TryptophanumHMDB
ArdeydormHMDB
L TryptophanHMDB
L-Tryptophan-ratiopharmHMDB
Merck brand OF tryptophanHMDB
Niddapharm brand OF tryptophanHMDB
ICN brand OF tryptophanHMDB
LevotryptophanHMDB
PMS TryptophanHMDB
PMS-TryptophanHMDB
Ratiopharm brand OF tryptophanHMDB
Esparma brand OF tryptophanHMDB
Ratio-tryptophanHMDB
L Tryptophan ratiopharmHMDB
NaturruheHMDB
Tryptophan metabolism alterationsHMDB
Ardeypharm brand OF tryptophanHMDB
Kalma brand OF tryptophanHMDB
Pharmascience brand OF tryptophanHMDB
Upsher-smith brand OF tryptophanHMDB
Ratio tryptophanHMDB
Molecular FormulaC11H12N2O2
Average Mass204.2252
Monoisotopic Mass204.089877638
IUPAC Name(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional NameL-tryptophan
CAS Registry Number73-22-3
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 KeyQIVBCDIJIAJPQS-VIFPVBQESA-N