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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:46:54 UTC

Update Date

2023-02-21 17:26:37 UTC

HMDB ID

HMDB0038462

Secondary Accession Numbers

HMDB38462

Metabolite Identification

Common Name

4-Hydroxy-1H-indole-3-acetonitrile

Description

4-Hydroxy-1H-indole-3-acetonitrile belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 4-Hydroxy-1H-indole-3-acetonitrile has been detected, but not quantified in, brassicas. This could make 4-hydroxy-1H-indole-3-acetonitrile a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Hydroxy-1H-indole-3-acetonitrile.

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       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.877  -3.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.907  -4.229   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    8                                                       
CONECT    3    1    9                                                       
CONECT    4    5    7                                                       
CONECT    5    4   11                                                       
CONECT    6    7   12                                                       
CONECT    7    4    6   10                                                  
CONECT    8    2   10   12                                                  
CONECT    9    3   10   13                                                  
CONECT   10    7    8    9                                                  
CONECT   11    5                                                            
CONECT   12    6    8                                                       
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(Cyanomethyl)-4-hydroxyindole	HMDB

Chemical Formula

C₁₀H₈N₂O

Average Molecular Weight

172.1833

Monoisotopic Molecular Weight

172.063662888

IUPAC Name

2-(4-hydroxy-1H-indol-3-yl)acetonitrile

Traditional Name

2-(4-hydroxy-1H-indol-3-yl)acetonitrile

CAS Registry Number

118573-52-7

SMILES

OC1=CC=CC2=C1C(CC#N)=CN2

InChI Identifier

InChI=1S/C10H8N2O/c11-5-4-7-6-12-8-2-1-3-9(13)10(7)8/h1-3,6,12-13H,4H2

InChI Key

RWBSUCOEZMIDSA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

3-alkylindole
Hydroxyindole
Indole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Nitrile
Carbonitrile
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038462)
Cytoplasm (HMDB: HMDB0038462)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038462)

Source

Exogenous

Food

Food (HMDB: HMDB0038462)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0038462)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038462)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.63 g/L	ALOGPS
logP	1.86	ALOGPS
logP	1.46	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.81 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.41 m³·mol⁻¹	ChemAxon
Polarizability	17.55 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.319	31661259
DarkChem	[M-H]-	136.14	31661259
DeepCCS	[M+H]+	136.817	30932474
DeepCCS	[M-H]-	133.764	30932474
DeepCCS	[M-2H]-	170.55	30932474
DeepCCS	[M+Na]+	146.088	30932474
AllCCS	[M+H]+	136.4	32859911
AllCCS	[M+H-H2O]+	132.0	32859911
AllCCS	[M+NH4]+	140.6	32859911
AllCCS	[M+Na]+	141.8	32859911
AllCCS	[M-H]-	136.2	32859911
AllCCS	[M+Na-2H]-	136.5	32859911
AllCCS	[M+HCOO]-	136.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-1H-indole-3-acetonitrile	OC1=CC=CC2=C1C(CC#N)=CN2	3076.3	Standard polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile	OC1=CC=CC2=C1C(CC#N)=CN2	1994.3	Standard non polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile	OC1=CC=CC2=C1C(CC#N)=CN2	2131.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-1H-indole-3-acetonitrile,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1C(CC#N)=C[NH]2	2002.2	Semi standard non polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile,1TMS,isomer #2	C[Si](C)(C)N1C=C(CC#N)C2=C(O)C=CC=C21	2020.5	Semi standard non polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1C(CC#N)=CN2[Si](C)(C)C	2084.8	Semi standard non polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1C(CC#N)=CN2[Si](C)(C)C	2083.3	Standard non polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(CC#N)=C[NH]2	2247.3	Semi standard non polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CC#N)C2=C(O)C=CC=C21	2250.2	Semi standard non polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(CC#N)=CN2[Si](C)(C)C(C)(C)C	2473.3	Semi standard non polar	33892256
4-Hydroxy-1H-indole-3-acetonitrile,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(CC#N)=CN2[Si](C)(C)C(C)(C)C	2527.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-0900000000-bdb410ea3f4d8d2915c6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8980000000-0bdbbb22e0a01b04e31e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 10V, Positive-QTOF	splash10-00di-0900000000-18da22ee0292c12af111	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 20V, Positive-QTOF	splash10-0a4i-0900000000-d63c6eab94a0e1cae1aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 40V, Positive-QTOF	splash10-0a4j-1900000000-daf4b0e5eee488aa3606	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 10V, Negative-QTOF	splash10-00di-0900000000-940ee958fbdc02c48719	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 20V, Negative-QTOF	splash10-00di-0900000000-741d997c6c7aea8ea93c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 40V, Negative-QTOF	splash10-0006-2900000000-fd0bb33cc0920eb13de9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 10V, Positive-QTOF	splash10-00di-0900000000-cfbd1ea6663ef51ca334	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 20V, Positive-QTOF	splash10-00di-0900000000-5a0a031f696f3f9f3bf0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 40V, Positive-QTOF	splash10-0v00-2900000000-24b5dd8221bd0ea3ae10	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 10V, Negative-QTOF	splash10-00di-0900000000-16cebe4b5caa7dbbf049	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 20V, Negative-QTOF	splash10-007o-0900000000-1f8453ba9c38ff24b9ca	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1H-indole-3-acetonitrile 40V, Negative-QTOF	splash10-0uxu-0900000000-ce3a3245bea4b55c4341	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017821

KNApSAcK ID

Not Available

Chemspider ID

9438778

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11263766

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Hydroxy-1H-indole-3-acetonitrile (HMDB0038462)

MOL for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

3D MOL for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

3D SDF for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

3D-SDF for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

PDB for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

3D PDB for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

SMILES for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

INCHI for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

Structure for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

3D Structure for HMDB0038462 (4-Hydroxy-1H-indole-3-acetonitrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra