MiMeDB: Showing metabocard for Indole-3-acetamide (MMDBc0049929)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:46:30 UTC

Update Date

2022-12-15 22:52:19 UTC

Metabolite ID

MMDBc0049929

Metabolite Identification

Common Name

Indole-3-acetamide

Description

Indole-3-acetamide, also known as 2-(3-indolyl)acetamide or IAM, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indole-3-acetamide has been detected, but not quantified, in several different foods, such as Alaska wild rhubarbs, lingonberries, butternut squash, pineapples, and agaves. Indole-3-acetamide is also found in the common pea and has been isolated from the etiolated seedlings of the black gram (Phaseolus mungo).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 05-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAY-20         0                                  
HETATM    1  C   UNK     0      -3.067   0.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.543  -0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.513  -2.131   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.007  -1.811   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.791   2.131   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.561   0.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.531  -0.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.876   0.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.715   1.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.210  -0.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.543   0.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.543   1.820   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       4.877  -0.490   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Synonyms

Value	Source
1H-Indole-3-acetamide	ChEBI
3-Indoleacetamide	ChEBI
Indoleacetamide	ChEBI
Auxin amide	MeSH
(indol-3-yl)Acetamide	HMDB
1-Indole-3-acetamide	HMDB
2-(1H-Indol-3-yl)acetamide	HMDB
2-(3-Indolyl)acetamide	HMDB
3-Indolylacetamide	HMDB
IAM	HMDB
Indole-3-acetamide	HMDB, KEGG
Indole-3-acetamide (6ci,8ci)	HMDB
Indole-3-acetamide (8ci)	HMDB
TSC	HMDB
TSR	HMDB

Molecular Formula

C₁₀H₁₀N₂O

Average Mass

174.1992

Monoisotopic Mass

174.079312952

IUPAC Name

2-(1H-indol-3-yl)acetamide

Traditional Name

indole-3-acetamide

CAS Registry Number

Not Available

SMILES

NC(=O)CC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)

InChI Key

ZOAMBXDOGPRZLP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:16031 )
acetamides (CHEBI:16031 )
a small molecule (CPD-237 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.67 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.9	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	15.94	ChemAxon
pKa (Strongest Basic)	-2.7	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	2	ChemAxon
Refractivity	50.27 m³·mol⁻¹	ChemAxon
Polarizability	18.23 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	66	Human feces; Human sputum; Human ; Human pleural fluid plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	148	Human feces; Human	Metabolic reconstruction
Bacteria	Actinobacteria	17	Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	13	Human ; Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria/NULL	Proteobacteria	2	Human feces; Human sputum; Human ; Human pleural fluid plaque	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0029739

DrugBank ID

DB08652

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

397

PDB ID

TSR

ChEBI ID

16031

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Indole-3-acetamide (MMDBc0049929)

MOL for #<Metabolite:0x00007f124152ab98>

3D MOL for #<Metabolite:0x00007f124152ab98>

3D SDF for #<Metabolite:0x00007f124152ab98>

3D-SDF for #<Metabolite:0x00007f124152ab98>

PDB for #<Metabolite:0x00007f124152ab98>

3D PDB for #<Metabolite:0x00007f124152ab98>

SMILES for #<Metabolite:0x00007f124152ab98>

INCHI for #<Metabolite:0x00007f124152ab98>

Structure for #<Metabolite:0x00007f124152ab98>

3D Structure for #<Metabolite:0x00007f124152ab98>