ChemFOnt: Showing chemical card for Indolepropionamide (CFc000220893)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:40:20 UTC

Chemfont ID

CFc000220893

Molecule Identification

Common Name

Indolepropionamide

Definition

Indolepropionamide (IPAM) is a product of tryptophan metabolism formed by symbiotic bacteria in the gastrointestinal tract of mammals. In particular, IPAM is an amide derivatization product of indole-3-propionic acid (IPA). IPAM reduces reactive oxygen species by inhibiting oxidative phosphorylation in complex I of the electron transport chain and acts as a stabilizer of energy metabolism, thereby reducing reactive oxygen species (ROS) production. In contrast to indole-3-propionic acid which bears a polar carboxyl group that is ionized at physiological pH carrying a negative charge, IPAM is non-polar and has sufficient lipophilicity to penetrate through biological membranes. In contrast to melatonin, IPAM is a "reversed amide" lacking the methoxy group as an aromatic substituent. In contrast to IPAM, melatonin is quickly metabolized in the liver by hydroxylation and excreted as the glucuronide or sulfate conjugate of 6-hydroxymelatonin (a pro-oxidant metabolite). IPAM, however, has a long half-life and no pro-oxidant activity (PMID: 20421998 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(1H-indol-3-yl)Propanamide	HMDB
3-(3-Indolyl)propanamide	HMDB
3-indol-3-Ylpropionamide	HMDB
3-Indolepropanamide	HMDB
IPAM	HMDB
Indole-3-propionamide	HMDB
Indolepropionamide	HMDB

Chemical Formula

C₁₁H₁₂N₂O

Average Molecular Weight

188.23

Monoisotopic Molecular Weight

188.094963014

IUPAC Name

3-(1H-indol-3-yl)propanamide

Traditional Name

3-(1H-indol-3-yl)propanamide

CAS Registry Number

5814-93-7

SMILES

NC(=O)CCC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C11H12N2O/c12-11(14)6-5-8-7-13-10-4-2-1-3-9(8)10/h1-4,7,13H,5-6H2,(H2,12,14)

InChI Key

OTVHXWFANORBAK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Triptan
3-alkylindole
Indole
Fatty amide
Substituted pyrrole
Benzenoid
Fatty acyl
Pyrrole
Heteroaromatic compound
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0240640)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.76 g/L	ALOGPS
logP	1.51	ALOGPS
logP	1.35	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	16.06	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.88 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.88 m³·mol⁻¹	ChemAxon
Polarizability	20.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240640

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

312353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indolepropionamide

METLIN ID

Not Available

PubChem Compound

351791

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Indolepropionamide (CFc000220893)

MOL for CFc000220893 (Indolepropionamide)

3D MOL for CFc000220893 (Indolepropionamide)

3D SDF for CFc000220893 (Indolepropionamide)

3D-SDF for CFc000220893 (Indolepropionamide)

PDB for CFc000220893 (Indolepropionamide)

3D PDB for CFc000220893 (Indolepropionamide)

SMILES for CFc000220893 (Indolepropionamide)

INCHI for CFc000220893 (Indolepropionamide)

Structure for CFc000220893 (Indolepropionamide)

3D Structure for CFc000220893 (Indolepropionamide)