MiMeDB: Showing metabocard for 3-(Hydroxyacetyl)-indole (MMDBc0003181)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 21:17:09 UTC

Update Date

2024-04-30 19:33:51 UTC

Metabolite ID

MMDBc0003181

Metabolite Identification

Common Name

3-(Hydroxyacetyl)-indole

Description

Hydroxymethyl indol-3-yl ketone belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Hydroxymethyl indol-3-yl ketone has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make hydroxymethyl indol-3-yl ketone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Hydroxymethyl indol-3-yl ketone.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -0.332  -1.653   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    8   11                                                       
CONECT    6   10   12                                                       
CONECT    7    3    8    9                                                  
CONECT    8    5    7   10                                                  
CONECT    9    4    7   11                                                  
CONECT   10    6    8   13                                                  
CONECT   11    5    9                                                       
CONECT   12    6                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Synonyms

Value	Source
3-(Hydroxyacetyl)indole	ChEMBL, HMDB, MeSH
3-(Hydroxylacetyl)-indole	ChEMBL, HMDB
2-Hydroxy-1-(1H-indol-3-yl)-ethanone	HMDB
2-Hydroxy-1-(1H-indol-3-yl)ethanone	HMDB
2-Hydroxy-1-(1H-indol-3-yl)ethanone, 9ci	HMDB
3-Glyceroindole	HMDB
Hydroxymethyl indol-3-yl ketone, 8ci	HMDB
INDOLE-3-ketol	HMDB

Molecular Formula

C₁₀H₉NO₂

Average Mass

175.184

Monoisotopic Mass

175.063328537

IUPAC Name

2-hydroxy-1-(1H-indol-3-yl)ethan-1-one

Traditional Name

2-hydroxy-1-(1H-indol-3-yl)ethanone

CAS Registry Number

Not Available

SMILES

OCC(=O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C10H9NO2/c12-6-10(13)8-5-11-9-4-2-1-3-7(8)9/h1-5,11-12H,6H2

InChI Key

IBLZDDPFMAFWKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Aryl ketone
Aryl alkyl ketone
Substituted pyrrole
Benzenoid
Alpha-hydroxy ketone
Pyrrole
Vinylogous amide
Heteroaromatic compound
Ketone
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (INDOLE-3-KETOL )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.11 g/L	ALOGPS
logP	1.23	ALOGPS
logP	0.81	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.25 m³·mol⁻¹	ChemAxon
Polarizability	18.02 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1900000000-f0354f847d1bcba7e54f	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-7920000000-76da93fdc1f5a0d4564d	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-48f9d541dc7ff0d5d8c4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056u-0900000000-18c2302d18bc0cc781cf	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066u-3900000000-a61a12d6c203976c2aca	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-6daee98b47fb048dfe0f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01bc-0900000000-b864bf3cf02b9c22bf51	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2900000000-6da6e7a304522040bf0e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0900000000-56cb2878a848064fa24f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6u-1900000000-ecffaafaba460720cf07	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-3900000000-7552a431a3b2ae857c53	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-d342c55bd638424704a5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-0900000000-6ccc28bf8c18f592876e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-326abb80dd4d99983eec	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

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

Metabolic Reactions

Not Available

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
Eukaryota/Fungi	Basidiomycota	3	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	2	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant		Pleurotus ostreatus	FooDB	31437929
Plant		Agaricus bisporus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0038628

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018022

KNApSAcK ID

C00041264

Chemspider ID

173681

KEGG Compound ID

Not Available

BioCyc ID

INDOLE-3-KETOL

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

200631

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]
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 3-(Hydroxyacetyl)-indole (MMDBc0003181)

MOL for #<Metabolite:0x00007f46e07f9738>

3D MOL for #<Metabolite:0x00007f46e07f9738>

3D SDF for #<Metabolite:0x00007f46e07f9738>

3D-SDF for #<Metabolite:0x00007f46e07f9738>

PDB for #<Metabolite:0x00007f46e07f9738>

3D PDB for #<Metabolite:0x00007f46e07f9738>

SMILES for #<Metabolite:0x00007f46e07f9738>

INCHI for #<Metabolite:0x00007f46e07f9738>

Structure for #<Metabolite:0x00007f46e07f9738>

3D Structure for #<Metabolite:0x00007f46e07f9738>