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Record Information
Version2.0
Created at2006-05-22 14:17:48 UTC
Updated at2021-06-29 00:47:33 UTC
NP-MRD IDNP0001120
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Methoxytryptophan
Description5-Methoxytryptophan is an L-tryptophan derivative that is L-tryptophan with a methoxy substituent at position 5. It has a role as a metabolite. It derives from a L-tryptophan. It is a tautomer of a 5-methoxy-L-tryptophan zwitterion. 5-Methoxytryptophan 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. Outside of the human body, 5-Methoxytryptophan has been detected, but not quantified in cow milk. 5-Methoxytryptophan is reduced in the urine of patients with liver disease. 5-Methoxytryptophan is reduced in the urine of parients with liver disease.
Structure
Thumb
Synonyms
ValueSource
5-Methoxytryptophan, (L)-isomerHMDB
5-Methoxytryptophan, (DL)-isomerHMDB
Chemical FormulaC12H14N2O3
Average Mass234.2512 Da
Monoisotopic Mass234.10044 Da
IUPAC Name(2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoic acid
Traditional Name5-methoxytryptophan
CAS Registry Number2504-22-5
SMILES
COC1=CC2=C(NC=C2C[C@H](N)C(O)=O)C=C1
InChI Identifier
InChI=1S/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1
InChI KeyKVNPSKDDJARYKK-JTQLQIEISA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
  • L-alpha-amino acid
  • 3-alkylindole
  • Indole
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.83 g/LALOGPS
logP-1ALOGPS
logP-1.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.22ChemAxon
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area88.34 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.67 m³·mol⁻¹ChemAxon
Polarizability24 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002339
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022969
KNApSAcK IDNot Available
Chemspider ID133110
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6631
PubChem Compound151018
PDB IDNot Available
ChEBI ID74049
Good Scents IDNot Available
References
General References
  1. Geffard M, Dulluc J, Rock AM: Antisera against the indolealkylamines: tryptophan, 5-hydroxytryptophan, 5-hydroxytryptamine, 5-methoxytryptophan, and 5-methoxytryptamine tested by an enzyme-linked immunosorbent assay method. J Neurochem. 1985 Apr;44(4):1221-8. [PubMed:3919158 ]
  2. Cheng HH, Kuo CC, Yan JL, Chen HL, Lin WC, Wang KH, Tsai KK, Guven H, Flaberg E, Szekely L, Klein G, Wu KK: Control of cyclooxygenase-2 expression and tumorigenesis by endogenous 5-methoxytryptophan. Proc Natl Acad Sci U S A. 2012 Aug 14;109(33):13231-6. doi: 10.1073/pnas.1209919109. Epub 2012 Jul 31. [PubMed:22851770 ]