ChemFOnt: Showing chemical card for Oxitriptan (CFc000009833)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:05 UTC

Chemfont ID

CFc000009833

Molecule Identification

Common Name

Oxitriptan

Definition

5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters serotonin and melatonin from tryptophan. 5-HTP is sold over-the-counter in the United Kingdom, United States and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid, and is also marketed in many European countries for the indication of major depression under trade names like 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Hydroxytryptophan L-form	ChEBI
Cincofarm	ChEBI
L-5-Hydroxytryptophan	ChEBI
Levothym	ChEBI
Oxitriptan	ChEBI
Tript-OH	ChEBI
Hydroxy-5 L-tryptophane	HMDB
5-HTP	HMDB
Hydroxytryptophan	HMDB
5-Hydroxytryptophan	HMDB
5 Hydroxytryptophan	HMDB
5-Hydroxy- tryptophan	HMDB
Oxytryptophan	HMDB
Tryptophan, 5 hydroxy	HMDB
(S)-5-Hydroxytryptophan	HMDB
5-Hydroxyl-L-tryptophan	HMDB
Levotonine	HMDB
Oxyfan	HMDB
Pretonine	HMDB
Quietim	HMDB
Serotonyl	HMDB
Telesol	HMDB
Triptene	HMDB
Triptum	HMDB
L-5-HTP	HMDB
5-Hydroxy-L-tryptophan	HMDB

Chemical Formula

C₁₁H₁₂N₂O₃

Average Molecular Weight

220.2246

Monoisotopic Molecular Weight

220.08479226

IUPAC Name

(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

Traditional Name

hydroxytryptophan

CAS Registry Number

4350-09-8

SMILES

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

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 Key

LDCYZAJDBXYCGN-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:17780 )
5-hydroxytryptophan (CHEBI:17780 )
hydroxy-L-tryptophan (CHEBI:17780 )

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Aromatic L-amino acid decarboxylase deficiency (HMDB: HMDB0015571)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)
Cerebrospinal fluid (HMDB: HMDB0015571)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)
Feces (HMDB: HMDB0015571)

Cellular substructure

Cytoplasm (HMDB: HMDB0015571)

Organ

Prostate (HMDB: HMDB0015571)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0015571)

Source

Exogenous

Exogenous (HMDB: HMDB0015571)

Food

Food (HMDB: HMDB0015571)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Tropical fruit

French plantain (FooDB: FOOD00436)

Endogenous

Endogenous (HMDB: HMDB0015571)

Plant

Plant (HMDB: HMDB0015571)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (HMDB: HMDB0015571)
Tryptophan Metabolism (HMDB: HMDB0015571)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0015571)

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0015571)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.63 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.34 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.18 m³·mol⁻¹	ChemAxon
Polarizability	22.03 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