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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:26 UTC

Update Date

2023-02-21 17:19:57 UTC

HMDB ID

HMDB0031172

Secondary Accession Numbers

HMDB31172

Metabolite Identification

Common Name

3-Formyl-6-hydroxyindole

Description

3-Formyl-6-hydroxyindole belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Based on a literature review very few articles have been published on 3-Formyl-6-hydroxyindole.

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       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454   0.000   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       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       1.340   3.801   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    7    9                                                       
CONECT    4    6   10                                                       
CONECT    5    6   11                                                       
CONECT    6    4    5    8                                                  
CONECT    7    1    3   12                                                  
CONECT    8    2    6    9                                                  
CONECT    9    3    8   10                                                  
CONECT   10    4    9                                                       
CONECT   11    5                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₇NO₂

Average Molecular Weight

161.1574

Monoisotopic Molecular Weight

161.047678473

IUPAC Name

6-hydroxy-1H-indole-3-carbaldehyde

Traditional Name

6-hydroxy-1H-indole-3-carbaldehyde

CAS Registry Number

192184-71-7

SMILES

OC1=CC2=C(C=C1)C(C=O)=CN2

InChI Identifier

InChI=1S/C9H7NO2/c11-5-6-4-10-9-3-7(12)1-2-8(6)9/h1-5,10,12H

InChI Key

FAFBOYSDWMRMLQ-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

Hydroxyindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Aryl-aldehyde
Substituted pyrrole
Benzenoid
Pyrrole
Vinylogous amide
Heteroaromatic compound
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aldehyde
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031172)
Cytoplasm (HMDB: HMDB0031172)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031172)

Source

Endogenous

Endogenous (HMDB: HMDB0031172)

Plant

Plant (HMDB: HMDB0031172)

Exogenous

Food

Food (HMDB: HMDB0031172)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0031172)

Process

Not Available

Role

Not Available

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	2.32 g/L	ALOGPS
logP	1.54	ALOGPS
logP	1.48	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-5.5	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	1	ChemAxon
Refractivity	45.71 m³·mol⁻¹	ChemAxon
Polarizability	16.02 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	135.002	31661259
DarkChem	[M-H]-	134.028	31661259
DeepCCS	[M+H]+	128.792	30932474
DeepCCS	[M-H]-	124.942	30932474
DeepCCS	[M-2H]-	162.45	30932474
DeepCCS	[M+Na]+	137.981	30932474
AllCCS	[M+H]+	134.1	32859911
AllCCS	[M+H-H2O]+	129.5	32859911
AllCCS	[M+NH4]+	138.3	32859911
AllCCS	[M+Na]+	139.6	32859911
AllCCS	[M-H]-	132.4	32859911
AllCCS	[M+Na-2H]-	132.9	32859911
AllCCS	[M+HCOO]-	133.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Formyl-6-hydroxyindole	OC1=CC2=C(C=C1)C(C=O)=CN2	3001.3	Standard polar	33892256
3-Formyl-6-hydroxyindole	OC1=CC2=C(C=C1)C(C=O)=CN2	2027.4	Standard non polar	33892256
3-Formyl-6-hydroxyindole	OC1=CC2=C(C=C1)C(C=O)=CN2	2099.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Formyl-6-hydroxyindole,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(C=O)=C[NH]C2=C1	2006.1	Semi standard non polar	33892256
3-Formyl-6-hydroxyindole,1TMS,isomer #2	C[Si](C)(C)N1C=C(C=O)C2=CC=C(O)C=C21	2036.3	Semi standard non polar	33892256
3-Formyl-6-hydroxyindole,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(C=O)=CN([Si](C)(C)C)C2=C1	2138.4	Semi standard non polar	33892256
3-Formyl-6-hydroxyindole,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(C=O)=CN([Si](C)(C)C)C2=C1	2119.3	Standard non polar	33892256
3-Formyl-6-hydroxyindole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(C=O)=C[NH]C2=C1	2249.0	Semi standard non polar	33892256
3-Formyl-6-hydroxyindole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(C=O)C2=CC=C(O)C=C21	2271.9	Semi standard non polar	33892256
3-Formyl-6-hydroxyindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(C=O)=CN([Si](C)(C)C(C)(C)C)C2=C1	2517.5	Semi standard non polar	33892256
3-Formyl-6-hydroxyindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(C=O)=CN([Si](C)(C)C(C)(C)C)C2=C1	2494.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Formyl-6-hydroxyindole GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-0900000000-afcc9517f62d2cfc4374	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Formyl-6-hydroxyindole GC-MS (1 TMS) - 70eV, Positive	splash10-02mi-5940000000-6032193dcc9f4fc68ba6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Formyl-6-hydroxyindole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Formyl-6-hydroxyindole 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 - 3-Formyl-6-hydroxyindole 10V, Positive-QTOF	splash10-03di-0900000000-acdb0fcdeb950671b00f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 20V, Positive-QTOF	splash10-03di-0900000000-7b9af0252d6d0bf25c60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 40V, Positive-QTOF	splash10-000x-1900000000-bfe1c39ff55abc17991a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 10V, Negative-QTOF	splash10-03di-0900000000-6582058ea8986be43c6f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 20V, Negative-QTOF	splash10-03di-0900000000-a46064e1a44256e77275	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 40V, Negative-QTOF	splash10-01qc-2900000000-d974809351ac728e75f4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 10V, Positive-QTOF	splash10-03di-0900000000-e754899e81d7b57dc135	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 20V, Positive-QTOF	splash10-03dl-0900000000-2648b682a1fc58ccbb54	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 40V, Positive-QTOF	splash10-0lec-6900000000-fb981c9151196dbffb05	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 10V, Negative-QTOF	splash10-03di-0900000000-6398a478231997ace291	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 20V, Negative-QTOF	splash10-001i-0900000000-b4fe14c5f6dbbd96406d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Formyl-6-hydroxyindole 40V, Negative-QTOF	splash10-0kai-1900000000-f4dff65266bfec926015	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB003188

KNApSAcK ID

Not Available

Chemspider ID

8278966

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10103438

PDB ID

Not Available

ChEBI ID

563251

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 3-Formyl-6-hydroxyindole (HMDB0031172)

MOL for HMDB0031172 (3-Formyl-6-hydroxyindole)

3D MOL for HMDB0031172 (3-Formyl-6-hydroxyindole)

3D SDF for HMDB0031172 (3-Formyl-6-hydroxyindole)

3D-SDF for HMDB0031172 (3-Formyl-6-hydroxyindole)

PDB for HMDB0031172 (3-Formyl-6-hydroxyindole)

3D PDB for HMDB0031172 (3-Formyl-6-hydroxyindole)

SMILES for HMDB0031172 (3-Formyl-6-hydroxyindole)

INCHI for HMDB0031172 (3-Formyl-6-hydroxyindole)

Structure for HMDB0031172 (3-Formyl-6-hydroxyindole)

3D Structure for HMDB0031172 (3-Formyl-6-hydroxyindole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra