MiMeDB: Showing metabocard for 3-Indoleacetonitrile (MMDBc0047993)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-12-11 00:19:26 UTC

Update Date

2022-09-01 02:13:49 UTC

Metabolite ID

MMDBc0047993

Metabolite Identification

Common Name

3-Indoleacetonitrile

Description

3-Indoleacetonitrile is a phytoalexin. Phytoalexins are antibiotics produced by plants that are under attack. Phytoalexins tend to fall into several classes including terpenoids, glycosteroids, and alkaloids; however, researchers often find it convenient to extend the definition to include all phytochemicals that are part of the plant's defensive arsenal. Phytoalexins produced in plants act as toxins to the attacking organism. They may puncture the cell wall, delay maturation, disrupt metabolism, or prevent the reproduction of the pathogen in question. However, phytoalexins are often targeted to specific predators; a plant that has anti-insect phytoalexins may not have the ability to repel a fungal attack. 3-Indoleacetonitrile is common in cruciferous vegetables such as cabbage, cauliflower, broccoli, and Brussels sprouts. Dietary indoles in cruciferous vegetables induce cytochrome P450 enzymes and have prevented tumours in various animal models. Consumption of Brassica vegetables is associated with a reduced risk of cancer of the alimentary tract in animal models and human populations (PMID:15612779 , 15884814 , 2342128 , 3014947 , 3880668 , 6334634 , 6419397 , 6426808 , 6584878 , 6725517 , 6838646 , 7123561 ).

Structure

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

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-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  N   UNK     0       3.543   1.820   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   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Synonyms

Value	Source
(indol-3-yl)Acetonitrile	ChEBI
(Indole-3-yl)acetonitrile	ChEBI
3-(Cyanomethyl)indole	ChEBI
3-Indolylacetonitrile	ChEBI
indol-3-Ylacetonitrile	ChEBI
Indole-3-acetonitrile	Kegg
(3-Indolyl)acetonitrile	HMDB
1H-indol-3-Ylacetonitrile	HMDB
1H-Indole-3-acetonitrile	HMDB
3-Cyanomethyl-1H-indole	HMDB
3-Indolacetonitrile	HMDB
3-Indolyl-acetonitrile	HMDB
b-Indoleacetonitrile	HMDB
beta-Indoleacetonitrile	HMDB
IAN	HMDB
Indoleacetonitrile	HMDB
Indolyl-3-acetonitrile	HMDB
Indolylacetonitril	HMDB
Indolylacetonitrile	HMDB
Usaf CB-29	HMDB
3-Indoleacetonitrile	ChEBI
(1H-Indol-3-yl)acetonitrile	HMDB

Molecular Formula

C₁₀H₈N₂

Average Mass

156.1839

Monoisotopic Mass

156.068748266

IUPAC Name

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

Traditional Name

indole-3-acetonitrile

CAS Registry Number

Not Available

SMILES

N#CCC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2

InChI Key

DMCPFOBLJMLSNX-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
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:17566 )
nitrile (CHEBI:17566 )
a small molecule (INDOLEYL-CPD )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.5 g/L	ALOGPS
logP	2.73	ALOGPS
logP	1.77	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.58 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.43 m³·mol⁻¹	ChemAxon
Polarizability	16.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

Mitochondria

Biospecimen Locations

Blood
Urine

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
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo_sapiens

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
Bacteria	Proteobacteria	1
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0006524

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

351795

PDB ID

Not Available

ChEBI ID

17566

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Michnovicz JJ, Bradlow HL: Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990 Jun 6;82(11):947-9. doi: 10.1093/jnci/82.11.947. [PubMed:2342128 ]
Bais R, James HM, Rofe AM, Conyers RA: The purification and properties of human liver ketohexokinase. A role for ketohexokinase and fructose-bisphosphate aldolase in the metabolic production of oxalate from xylitol. Biochem J. 1985 Aug 15;230(1):53-60. doi: 10.1042/bj2300053. [PubMed:2996495 ]
Bradlow HL, Hershcopf R, Martucci C, Fishman J: 16 alpha-hydroxylation of estradiol: a possible risk marker for breast cancer. Ann N Y Acad Sci. 1986;464:138-51. doi: 10.1111/j.1749-6632.1986.tb16001.x. [PubMed:3014947 ]
Degawa M, Kojima M, Hishinuma T, Hashimoto Y: Sex-dependent induction of hepatic enzymes for mutagenic activation of a tryptophan pyrolysate component, 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]-indole, by feeding in mice. Cancer Res. 1985 Jan;45(1):96-102. [PubMed:3880668 ]
James HM, Bais R, Edwards JB, Rofe AM, Conyers AJ: Models for the metabolic production of oxalate from xylitol in humans: a role for fructokinase and aldolase. Aust J Exp Biol Med Sci. 1982 Feb;60(Pt 1):117-22. doi: 10.1038/icb.1982.11. [PubMed:6284103 ]
Bradfield CA, Bjeldanes LF: Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase, glutathione S-transferase and epoxide hydrolase activities in the rat. Food Chem Toxicol. 1984 Dec;22(12):977-82. doi: 10.1016/0278-6915(84)90147-9. [PubMed:6334634 ]
Eisele TA, Bailey GS, Nixon JE: The effect of indole-3-carbinol, an aflatoxin B1 hepatocarcinoma inhibitor, and other indole analogs on the rainbow trout hepatic mixed function oxidase system. Toxicol Lett. 1983 Oct-Nov;19(1-2):133-8. doi: 10.1016/0378-4274(83)90273-4. [PubMed:6419397 ]
Nixon JE, Hendricks JD, Pawlowski NE, Pereira CB, Sinnhuber RO, Bailey GS: Inhibition of aflatoxin B1 carcinogenesis in rainbow trout by flavone and indole compounds. Carcinogenesis. 1984 May;5(5):615-9. doi: 10.1093/carcin/5.5.615. [PubMed:6426808 ]
Barngrover DA, Stevens HC, Dills WL Jr: D-Xylulose-1-phosphate: enzymatic assay and production in isolated rat hepatocytes. Biochem Biophys Res Commun. 1981 Sep 16;102(1):75-80. doi: 10.1016/0006-291x(81)91490-x. [PubMed:6458298 ]
Kappas A, Anderson KE, Conney AH, Pantuck EJ, Fishman J, Bradlow HL: Nutrition-endocrine interactions: induction of reciprocal changes in the delta 4-5 alpha-reduction of testosterone and the cytochrome P-450-dependent oxidation of estradiol by dietary macronutrients in man. Proc Natl Acad Sci U S A. 1983 Dec;80(24):7646-9. doi: 10.1073/pnas.80.24.7646. [PubMed:6584878 ]
Anderson KE, Kappas A, Conney AH, Bradlow HL, Fishman J: The influence of dietary protein and carbohydrate on the principal oxidative biotransformations of estradiol in normal subjects. J Clin Endocrinol Metab. 1984 Jul;59(1):103-7. doi: 10.1210/jcem-59-1-103. [PubMed:6725517 ]
Bulger WH, Kupfer D: Effect of xenobiotic estrogens and structurally related compounds on 2-hydroxylation of estradiol and on other monooxygenase activities in rat liver. Biochem Pharmacol. 1983 Mar 15;32(6):1005-10. doi: 10.1016/0006-2952(83)90618-4. [PubMed:6838646 ]
Shertzer HG: Indole-3-carbinol and indole-3-acetonitrile influence on hepatic microsomal metabolism. Toxicol Appl Pharmacol. 1982 Jun 30;64(2):353-61. doi: 10.1016/0041-008x(82)90229-0. [PubMed:7123561 ]
GHALAMBOR MA, HEATH EC: The metabolism of L-fucose. II. The enzymatic cleavage of L-fuculose 1-phosphate. J Biol Chem. 1962 Aug;237:2427-33. [PubMed:13898172 ]
Ciska E, Pathak DR: Glucosinolate derivatives in stored fermented cabbage. J Agric Food Chem. 2004 Dec 29;52(26):7938-43. doi: 10.1021/jf048986+. [PubMed:15612779 ]
Smith TK, Lund EK, Clarke RG, Bennett RN, Johnson IT: Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro. J Agric Food Chem. 2005 May 18;53(10):3895-901. doi: 10.1021/jf048025v. [PubMed:15884814 ]

Showing metabocard for 3-Indoleacetonitrile (MMDBc0047993)

MOL for #<Metabolite:0x00007f1240fbfbe0>

3D MOL for #<Metabolite:0x00007f1240fbfbe0>

3D SDF for #<Metabolite:0x00007f1240fbfbe0>

3D-SDF for #<Metabolite:0x00007f1240fbfbe0>

PDB for #<Metabolite:0x00007f1240fbfbe0>

3D PDB for #<Metabolite:0x00007f1240fbfbe0>

SMILES for #<Metabolite:0x00007f1240fbfbe0>

INCHI for #<Metabolite:0x00007f1240fbfbe0>

Structure for #<Metabolite:0x00007f1240fbfbe0>

3D Structure for #<Metabolite:0x00007f1240fbfbe0>