ChemFOnt: Showing chemical card for (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid (CFc000018858)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:09:32 UTC

Chemfont ID

CFc000018858

Molecule Identification

Common Name

(1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid

Definition

(1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid is found in alcoholic beverages. (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid is widespread in many foodstuffs especially fruit juices, jams and fermented foods or beverages including beer and soy sauce. Also present in the toxic fly agaric mushroom (Amanita muscaria). (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid is formed by Pictet-Spengler condensation between acetaldehyde and L-tryptophan in nature or during food processing.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-b-carboline-3-carboxylate	Generator
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-b-carboline-3-carboxylic acid	Generator
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-beta-carboline-3-carboxylate	Generator
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylate	Generator
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylic acid	Generator
MTCA	HMDB
1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid	HMDB
1-Methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate	HMDB

Chemical Formula

C₁₃H₁₄N₂O₂

Average Molecular Weight

230.2625

Monoisotopic Molecular Weight

230.105527702

IUPAC Name

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

Traditional Name

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

CAS Registry Number

None

SMILES

CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O

InChI Identifier

InChI=1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17)

InChI Key

ZUPHXNBLQCSEIA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Secondary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037942)
Cytoplasm (HMDB: HMDB0037942)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037942)

Source

Exogenous

Exogenous (HMDB: HMDB0037942)

Food

Food (HMDB: HMDB0037942)

Vegetable

Mushroom

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0037942)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037942)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	0.04	ALOGPS
logP	-0.77	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	63.83 m³·mol⁻¹	ChemAxon
Polarizability	24.8 Å³	ChemAxon
Number of Rings	3	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

HMDB0037942

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017111

KNApSAcK ID

Not Available

Chemspider ID

66213

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73530

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid (CFc000018858)

MOL for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

3D MOL for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

3D SDF for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

3D-SDF for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

PDB for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

3D PDB for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

SMILES for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

INCHI for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

Structure for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

3D Structure for CFc000018858 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)