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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:28:47 UTC
HMDB IDHMDB0000472
Secondary Accession Numbers
  • HMDB0000504
  • HMDB0015571
  • HMDB00472
  • HMDB00504
  • HMDB15571
Metabolite Identification
Common Name5-Hydroxy-L-tryptophan
Description5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid L-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic L-amino acid decarboxylase (EC 4.1.1.28) (AADC1 also known as DOPA decarboxylase), an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency (AADC deficiency) (OMIM: 608643 ) accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific. 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinson's patients with severe postural instability and gait disorders. The amount of endogenous 5-hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase (EC 1.14.16.4), indoleamine 2,3-dioxygenase (EC 1.13.11.52), and tryptophan 2,3-dioxygenase (TDO) (EC 1.13.11.11). 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to its use in the treatment of depression, the therapeutic administration of 5-hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties (PMID: 9295177 , 17240182 , 16023217 ). When present in sufficiently high levels, 5-hydroxytryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells or tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Signs and symptoms of AADC deficiency generally appear in the first year of life. Affected infants may have severe developmental delay, weak muscle tone (hypotonia), muscle stiffness, difficulty moving, and involuntary writhing movements of the limbs (athetosis). They may be lacking in energy (lethargic), feed poorly, startle easily, and have sleep disturbances. Since 5-hydroxytryptophan is a precursor to serotonin, altered levels of serotonin can accumulate in the brain, which leads to abnormal neural signalling. Infants with AADC deficiency have very low levels of neural signalling molecules while individuals who consume high levels of 5-hydroxytryptophan will have very high levels of neural signalling molecules. Both conditions can lead to vomiting, nausea, extreme drowsiness, and lethargy. 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN) is sold over-the-counter in the United Kingdom, the United States, and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid. It is also marketed in many European countries for the indication of major depression under trade names such as Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high-quality studies has been noted. More and larger studies are needed to determine if 5-HTP is truly effective in treating depression.
Structure
Data?1582752133
Synonyms
ValueSource
5-Hydroxytryptophan L-formChEBI
CincofarmChEBI
L-5-HydroxytryptophanChEBI
LevothymChEBI
OxitriptanChEBI
Tript-OHChEBI
Hydroxy-5 L-tryptophaneHMDB
5-HTPHMDB
HydroxytryptophanHMDB
5-HydroxytryptophanHMDB
5 HydroxytryptophanHMDB
5-Hydroxy- tryptophanHMDB
OxytryptophanHMDB
Tryptophan, 5 hydroxyHMDB
(S)-5-HydroxytryptophanHMDB
5-Hydroxyl-L-tryptophanHMDB
LevotonineHMDB
OxyfanHMDB
PretonineHMDB
QuietimHMDB
SerotonylHMDB
TelesolHMDB
TripteneHMDB
TriptumHMDB
L-5-HTPHMDB
5-Hydroxy-L-tryptophanHMDB
Chemical FormulaC11H12N2O3
Average Molecular Weight220.2246
Monoisotopic Molecular Weight220.08479226
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number4350-09-8
SMILESNot Available
InChI Identifier
InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1
InChI KeyLDCYZAJDBXYCGN-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
Alternative Parents
Substituents
  • Serotonin
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • L-alpha-amino acid
  • Hydroxyindole
  • Indole
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point293 - 298 °CNot Available
Boiling Point520.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility31500 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-2.051Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker153.72230932474
[M-H]-MetCCS_train_neg148.85830932474
[M+H]+Baker157.87730932474
[M-H]-Not Available153.722http://allccs.zhulab.cn/database/detail?ID=AllCCS00001799
[M+H]+Not Available157.877http://allccs.zhulab.cn/database/detail?ID=AllCCS00001799
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.13931661259
DarkChem[M-H]-149.64331661259
AllCCS[M+H]+149.70732859911
AllCCS[M-H]-149.19532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Hydroxy-L-tryptophanN[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O3889.4Standard polar33892256
5-Hydroxy-L-tryptophanN[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O2240.5Standard non polar33892256
5-Hydroxy-L-tryptophanN[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=O2669.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxy-L-tryptophan,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@H](N)C(=O)O)C2=C12494.7Semi standard non polar33892256
5-Hydroxy-L-tryptophan,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(O)C=C122426.4Semi standard non polar33892256
5-Hydroxy-L-tryptophan,1TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O2476.1Semi standard non polar33892256
5-Hydroxy-L-tryptophan,1TMS,isomer #4C[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC(O)=CC=C212497.4Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C122455.3Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O2473.2Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O)=CN2[Si](C)(C)C2513.3Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C2397.9Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C122416.7Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #6C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C2628.0Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TMS,isomer #7C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O2503.6Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C2437.9Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C2487.6Standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C2747.1Standard polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122476.4Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122447.6Standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122872.6Standard polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #3C[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C12594.1Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #3C[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C12569.1Standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #3C[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C2=C12883.0Standard polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O2499.0Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O2488.6Standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O2879.3Standard polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #5C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C2563.5Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #5C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C2597.2Standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #5C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C2829.6Standard polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #6C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C2412.7Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #6C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C2519.8Standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #6C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C2779.6Standard polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #7C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C2629.0Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #7C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C2628.3Standard non polar33892256
5-Hydroxy-L-tryptophan,3TMS,isomer #7C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C2925.0Standard polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C2619.8Semi standard non polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C2605.9Standard non polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C2638.3Standard polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C2478.9Semi standard non polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C2491.0Standard non polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)C(=O)O[Si](C)(C)C2615.3Standard polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C2653.1Semi standard non polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C2609.8Standard non polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C2750.8Standard polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C2607.8Semi standard non polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C2650.4Standard non polar33892256
5-Hydroxy-L-tryptophan,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C)[Si](C)(C)C2683.9Standard polar33892256
5-Hydroxy-L-tryptophan,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C2698.4Semi standard non polar33892256
5-Hydroxy-L-tryptophan,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C2619.4Standard non polar33892256
5-Hydroxy-L-tryptophan,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)N([Si](C)(C)C)[Si](C)(C)C2563.7Standard polar33892256
5-Hydroxy-L-tryptophan,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@H](N)C(=O)O)C2=C12790.8Semi standard non polar33892256
5-Hydroxy-L-tryptophan,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(O)C=C122733.2Semi standard non polar33892256
5-Hydroxy-L-tryptophan,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O2741.8Semi standard non polar33892256
5-Hydroxy-L-tryptophan,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC(O)=CC=C212769.7Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C123008.9Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O3044.3Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@H](N)C(=O)O)=CN2[Si](C)(C)C(C)(C)C3048.7Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C(C)(C)C2947.0Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C122944.0Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C3076.2Semi standard non polar33892256
5-Hydroxy-L-tryptophan,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O2999.7Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C3198.6Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C3139.3Standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C3020.0Standard polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C123216.2Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C123053.9Standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C123084.6Standard polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C13370.5Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C13196.8Standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C13085.9Standard polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O3265.6Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O3104.5Standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O3095.0Standard polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3275.0Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3227.7Standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3035.3Standard polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C(C)(C)C3120.1Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C(C)(C)C3156.5Standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O[Si](C)(C)C(C)(C)C3012.0Standard polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C3307.2Semi standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C3220.6Standard non polar33892256
5-Hydroxy-L-tryptophan,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)C(=O)O)[Si](C)(C)C(C)(C)C3090.8Standard polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3543.3Semi standard non polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3405.5Standard non polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3003.7Standard polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C3371.2Semi standard non polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C3268.7Standard non polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)C(=O)O[Si](C)(C)C(C)(C)C2998.6Standard polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C3565.2Semi standard non polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C3338.8Standard non polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C3040.2Standard polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3451.7Semi standard non polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3402.0Standard non polar33892256
5-Hydroxy-L-tryptophan,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2995.8Standard polar33892256
5-Hydroxy-L-tryptophan,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3718.7Semi standard non polar33892256
5-Hydroxy-L-tryptophan,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3486.6Standard non polar33892256
5-Hydroxy-L-tryptophan,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3008.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (4 TMS)splash10-0006-0390000000-d4e36a90b7591787e67b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (3 TMS)splash10-0006-1390000000-b0af49def87c0211653c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (3 TMS)splash10-014i-0390000000-8b7f6cc8f51c032dd86d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-EI-TOF (Non-derivatized)splash10-014i-0390000000-88191cf8140abf0f32052017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-EI-TOF (Non-derivatized)splash10-0006-0290000000-a30ea02ff8d4d14ba7a42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized)splash10-0006-0390000000-d4e36a90b7591787e67b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized)splash10-0006-1390000000-b0af49def87c0211653c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized)splash10-014i-0390000000-8b7f6cc8f51c032dd86d2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized) - 70eV, Positivesplash10-00bd-4920000000-c1f07beecfc6ada179c12017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9044000000-9dc0e361e3885451d81f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-L-tryptophan GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan LC-ESI-QTOF , positive-QTOFsplash10-0udi-0790000000-a699ed429ebd1609f9952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan LC-ESI-QTOF , positive-QTOFsplash10-03e9-0900000000-bbd302f8ff188f6cf93d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan LC-ESI-QTOF , positive-QTOFsplash10-053r-0900000000-6cc3ba396b1cfa8db1e62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan , positive-QTOFsplash10-053r-2900000000-90a465428eacaced71e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Positive-QTOFsplash10-0udi-0390000000-8d1a103c7fb1b7dfa6852021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 20V, Positive-QTOFsplash10-03di-0900000000-25de1fda6182de338d152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 30V, Positive-QTOFsplash10-053r-0900000000-e8cfeeeea0f83c87c0a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Positive-QTOFsplash10-0w29-0790000000-61308573c0d4d1caee8a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 0V, Positive-QTOFsplash10-0w90-0590000000-9c6aa4b5a920add9f8ea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Positive-QTOFsplash10-03di-0930000000-074911d5bc17a486cbb02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 0V, Positive-QTOFsplash10-0uk9-0190000000-9d6cad9671c04310ac0c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 30V, Positive-QTOFsplash10-05ox-2900000000-08b2a2c24032d96597db2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 20V, Negative-QTOFsplash10-000x-1900000000-9c83828dc6df75a0e7982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 30V, Negative-QTOFsplash10-001l-1900000000-dc720fc8e93906bb0c672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Negative-QTOFsplash10-014l-1970000000-6deb0cc19e89586090e62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 40V, Negative-QTOFsplash10-001l-0900000000-cab77201c86bda083dd02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 40V, Positive-QTOFsplash10-053r-1900000000-b1c220623de477b387ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 30V, Positive-QTOFsplash10-053r-0900000000-f7c54dfcc55add0c83d62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Positive-QTOFsplash10-00b9-0950000000-e3f9fbda111b2109f6302017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 20V, Positive-QTOFsplash10-004i-0900000000-b21f3fecc8ae15c125de2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 40V, Positive-QTOFsplash10-0002-0900000000-817e4d468ea1bf1a3bc32017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Negative-QTOFsplash10-014i-2190000000-65b1ee730ae09a2cd6a52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 20V, Negative-QTOFsplash10-00di-9650000000-68d73bfc7c9dd0f880e12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 40V, Negative-QTOFsplash10-00di-9600000000-c58badf19c5cbb2f43472017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-L-tryptophan 10V, Negative-QTOFsplash10-001i-1950000000-5df9078df2a62ba2dc7e2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.018 +/- 0.0027 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.005 (0.00-0.010) uMInfant (0-1 year old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.0100 uMChildren (1-13 years old)Female
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0078 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.063 uMInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0970-0.136 uMChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency
details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  1. Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
Associated OMIM IDs
  • 608643 (Aromatic L-amino acid decarboxylase deficiency)
  • 266600 (Crohn's disease)
  • 114500 (Colorectal cancer)
DrugBank IDDB02959
Phenol Explorer Compound IDNot Available
FooDB IDFDB006231
KNApSAcK IDC00001371
Chemspider ID388413
KEGG Compound IDC00643
BioCyc ID5-HYDROXY-TRYPTOPHAN
BiGG IDNot Available
Wikipedia Link5-Hydroxytryptophan
METLIN IDNot Available
PubChem Compound439280
PDB IDNot Available
ChEBI ID17780
Food Biomarker OntologyNot Available
VMH ID5HTRP
MarkerDB IDMDB00000169
Good Scents IDrw1700141
References
Synthesis ReferenceBoroda, E.; Rakowska, S.; Kanski, R.; Kanska, M. Enzymatic synthesis of L-tryptophan and 5'-hydroxy-L-tryptophan labeled with deuterium and tritium at the a-carbon position. Journal of Labelled Compounds & Radiopharmaceuticals (2003), 46(8), 691-698.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Magnussen I, Van Woert MH: Human pharmacokinetics of long term 5-hydroxytryptophan combined with decarboxylase inhibitors. Eur J Clin Pharmacol. 1982;23(1):81-6. [PubMed:6182005 ]
  3. Li Kam Wa TC, Freestone S, Samson RR, Johnson NR, Lee MR: A comparison of the renal and neuroendocrine effects of two 5-hydroxytryptamine renal prodrugs in normal man. Clin Sci (Lond). 1993 Nov;85(5):607-14. [PubMed:8287650 ]
  4. Li Kam Wa TC, Freestone S, Samson RR, Johnston NR, Lee MR: Renal metabolism and effects of the glutamyl derivatives of L-dopa and 5-hydroxytryptophan in man. Clin Sci (Lond). 1996 Aug;91(2):177-85. [PubMed:8795441 ]
  5. Iacono RP, Kuniyoshi SM, Ahlman JR, Zimmerman GJ, Maeda G, Pearlstein RD: Concentrations of indoleamine metabolic intermediates in the ventricular cerebrospinal fluid of advanced Parkinson's patients with severe postural instability and gait disorders. J Neural Transm (Vienna). 1997;104(4-5):451-9. [PubMed:9295177 ]
  6. Verbeek MM, Geurtz PB, Willemsen MA, Wevers RA: Aromatic L-amino acid decarboxylase enzyme activity in deficient patients and heterozygotes. Mol Genet Metab. 2007 Apr;90(4):363-9. Epub 2007 Jan 19. [PubMed:17240182 ]
  7. Turner EH, Loftis JM, Blackwell AD: Serotonin a la carte: supplementation with the serotonin precursor 5-hydroxytryptophan. Pharmacol Ther. 2006 Mar;109(3):325-38. Epub 2005 Jul 14. [PubMed:16023217 ]
  8. Bouchard S, Roberge AG: Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat. Can J Biochem. 1979 Jul;57(7):1014-8. [PubMed:39668 ]
  9. Amamoto T, Sarai K: On the tryptophan-serotonin metabolism in manic-depressive disorders. Changes in plasma 5-HT and 5-HIAA levels and urinary 5-HIAA excretion following oral loading of L-5HTP in patients with depression. Hiroshima J Med Sci. 1976 Sep;25(2-3):135-40. [PubMed:1088369 ]
  10. Caruso I, Sarzi Puttini P, Cazzola M, Azzolini V: Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome. J Int Med Res. 1990 May-Jun;18(3):201-9. [PubMed:2193835 ]
  11. De Benedittis G, Massei R: Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo. J Neurosurg Sci. 1985 Jul-Sep;29(3):239-48. [PubMed:3913752 ]
  12. Magnussen I, Jensen TS, Rand JH, Van Woert MH: Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man. Acta Pharmacol Toxicol (Copenh). 1981 Sep;49(3):184-9. [PubMed:6175178 ]
  13. Rahman MK, Nagatsu T, Sakurai T, Hori S, Abe M, Matsuda M: Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats. Jpn J Pharmacol. 1982 Oct;32(5):803-11. [PubMed:6983619 ]
  14. Sternberg EM, Van Woert MH, Young SN, Magnussen I, Baker H, Gauthier S, Osterland CK: Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa. N Engl J Med. 1980 Oct 2;303(14):782-7. [PubMed:6997735 ]
  15. Trouillas P, Serratrice G, Laplane D, Rascol A, Augustin P, Barroche G, Clanet M, Degos CF, Desnuelle C, Dumas R, et al.: Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study. Arch Neurol. 1995 May;52(5):456-60. [PubMed:7733839 ]
  16. Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [PubMed:9727088 ]
  17. Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. [PubMed:11869656 ]
  18. Turner EH, Blackwell AD: 5-Hydroxytryptophan plus SSRIs for interferon-induced depression: synergistic mechanisms for normalizing synaptic serotonin. Med Hypotheses. 2005;65(1):138-44. [PubMed:15893130 ]
  19. Nakatani Y, Sato-Suzuki I, Tsujino N, Nakasato A, Seki Y, Fumoto M, Arita H: Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat. Eur J Neurosci. 2008 May;27(9):2466-72. doi: 10.1111/j.1460-9568.2008.06201.x. [PubMed:18445233 ]

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
Reactions
5-Hydroxy-L-tryptophan → Serotonin + CO(2)details
5-Hydroxy-L-tryptophan → Serotonin + Carbon dioxidedetails
General function:
Involved in heme binding
Specific function:
Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:
IDO1
Uniprot ID:
P14902
Molecular weight:
45325.89
Reactions
5-Hydroxy-L-tryptophan + Oxygen → 5-Hydroxy-N-formylkynureninedetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH1
Uniprot ID:
P17752
Molecular weight:
50984.725
Reactions
L-Tryptophan + Tetrahydrobiopterin + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Hydroxytetrahydrobiopterindetails
Tetrahydrobiopterin + L-Tryptophan + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH2
Uniprot ID:
Q8IWU9
Molecular weight:
56056.295
Reactions
L-Tryptophan + Tetrahydrobiopterin + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Hydroxytetrahydrobiopterindetails
Tetrahydrobiopterin + L-Tryptophan + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
General function:
Involved in heme binding
Specific function:
Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
Gene Name:
IDO2
Uniprot ID:
Q6ZQW0
Molecular weight:
47074.745
Reactions
5-Hydroxy-L-tryptophan + Oxygen → 5-Hydroxy-N-formylkynureninedetails