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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-12 21:10:36 UTC

Update Date

2021-10-13 04:41:44 UTC

HMDB ID

HMDB0003447

Secondary Accession Numbers

HMDB03447

Metabolite Identification

Common Name

Tryptophol

Description

Tryptophol, also known as indole-3-ethanol, is an indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2. It has a role as a Saccharomyces cerevisiae metabolite, an auxin and a plant metabolite. Tryptophol is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID:30120222 ). Tryptophol production was negatively associated with interferon-gamma production (IFNγ) which suggests that tryptophol has anti-inflammatory properties (PMID:27814509 ). Tryptophol has also been identified as the hypnotic agent in trypanosomal sleeping sickness, and because it is formed in vivo after ethanol or disulfiram treatment, it is also associated with the study of alcoholism (PMID:7241135 ).

Structure

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

HEADER    PROTEIN                                 28-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JAN-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8669.1548664.625   0.000  0.00  0.00           O+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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1H-Indole-3-ethanol	ChEBI
1H-Indolyl-3-ethanol	ChEBI
2-(indol-3-yl)Ethanol	ChEBI
3-(2-Hydroxyethyl)indole	ChEBI
Indole-3-ethanol	ChEBI
Tryptophanol	ChEBI
2-(1H-indol-3-yl)Ethanol	HMDB
2-(3-Indolyl)ethanol	HMDB
2-(3-Indolylethanol	HMDB
3-(b-Hydroxyethyl)indole	HMDB
3-(beta-Hydroxyethyl)indole	HMDB
3-Indoleethanol	HMDB
3-Indolylethanol	HMDB
b-(3-Indole)ethanol	HMDB
beta-(3-Indole)ethanol	HMDB
beta-indol-3-Ylethanol	HMDB
DL-Tryptophanol	HMDB
IEA	HMDB
Indole ethanol	HMDB
Indoleethanol	HMDB
Tryptophol	HMDB, KEGG
3-(2-Hydroxyethyl)-1H-indole	HMDB
3-(β-Hydroxyethyl)indole	HMDB
3-Indole ethanol	HMDB
β-(3-Indole)ethanol	HMDB

Chemical Formula

C₁₀H₁₁NO

Average Molecular Weight

161.2004

Monoisotopic Molecular Weight

161.084063979

IUPAC Name

2-(1H-indol-3-yl)ethan-1-ol

Traditional Name

tryptophol

CAS Registry Number

526-55-6

SMILES

OCCC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2

InChI Key

MBBOMCVGYCRMEA-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
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolyl alcohol (CHEBI:17890 )
a small molecule (CPD-341 )

Ontology

Disposition

Biological location

Non-excretory biofluid

Blood

Excreta

Urine

Herbal tea

Herbal teas

Greenthread tea

Lentils

Onion-family vegetables

Cabbages

Other vegetables

Mushrooms

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Cocoa and cocoa products

Cocoa

Cocoa bean

Beverages

Fermented beverages

Beer

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Soy

Soy bean

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	59 °C	Not Available
Boiling Point	357.80 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2749 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.280 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	133.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002126
[M+H]+	Not Available	133.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002126

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.61 g/L	ALOGPS
logP	1.82	ALOGPS
logP	1.59	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	15.8	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	48.72 m³·mol⁻¹	ChemAxon
Polarizability	17.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.229	31661259
DarkChem	[M-H]-	132.255	31661259
DeepCCS	[M+H]+	134.151	30932474
DeepCCS	[M-H]-	130.35	30932474
DeepCCS	[M-2H]-	167.988	30932474
DeepCCS	[M+Na]+	143.287	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tryptophol	OCCC1=CNC2=C1C=CC=C2	2907.9	Standard polar	33892256
Tryptophol	OCCC1=CNC2=C1C=CC=C2	1719.2	Standard non polar	33892256
Tryptophol	OCCC1=CNC2=C1C=CC=C2	1769.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tryptophol,1TMS,isomer #1	C[Si](C)(C)OCCC1=C[NH]C2=CC=CC=C12	1821.7	Semi standard non polar	33892256
Tryptophol,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCO)C2=CC=CC=C21	1813.1	Semi standard non polar	33892256
Tryptophol,2TMS,isomer #1	C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1871.2	Semi standard non polar	33892256
Tryptophol,2TMS,isomer #1	C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1883.2	Standard non polar	33892256
Tryptophol,2TMS,isomer #1	C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1990.9	Standard polar	33892256
Tryptophol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=CC=C12	2078.0	Semi standard non polar	33892256
Tryptophol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCO)C2=CC=CC=C21	2070.5	Semi standard non polar	33892256
Tryptophol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2320.4	Semi standard non polar	33892256
Tryptophol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2302.9	Standard non polar	33892256
Tryptophol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2239.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Tryptophol GC-MS (2 TMS)	splash10-0udi-1591000000-5b173cc0ac0dc2b874a9	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tryptophol GC-MS (Non-derivatized)	splash10-0udi-1591000000-5b173cc0ac0dc2b874a9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tryptophol GC-EI-TOF (Non-derivatized)	splash10-0udi-0490000000-15708d306e1f75b1e76f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0900000000-d2769447ff27a79be367	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophol GC-MS (1 TMS) - 70eV, Positive	splash10-00yi-5690000000-765b6a566d2067c199b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tryptophol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-2900000000-20fec68981d54c2e7002	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-01ox-0900000000-5fb5f5b5efe809cbe9ad	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00kf-0900000000-44158c348db109504af4	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014l-6900000000-48b709f034a27e74e73f	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-03di-0900000000-593c6fbb6f64e16e7f05	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-03e9-0900000000-54f7b6548b8a00c91c3f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-003u-0900000000-fb2793cd76eefaaf45c5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-016r-0900000000-a97ae0f4c1633b83c415	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-014i-0900000000-d00c24bc728f46156c60	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOF	splash10-03di-0900000000-593c6fbb6f64e16e7f05	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOF	splash10-03e9-0900000000-54f7b6548b8a00c91c3f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOF	splash10-003u-0900000000-fb2793cd76eefaaf45c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOF	splash10-016r-0900000000-78c3b34c10c43b6a9317	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol LC-ESI-QQ , negative-QTOF	splash10-014i-0900000000-d00c24bc728f46156c60	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol , negative-QTOF	splash10-03di-0900000000-d41cd8e81a55b3e00538	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol 20V, Positive-QTOF	splash10-0006-0900000000-5927d4ac720f209af38d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol 40V, Positive-QTOF	splash10-00kf-5900000000-4bc97e2ed06c230bbbde	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol 10V, Positive-QTOF	splash10-0006-0900000000-4807fdc919bf8c468f72	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol 20V, Positive-QTOF	splash10-0006-0900000000-63222dc5b6f22cd7cc13	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tryptophol 40V, Positive-QTOF	splash10-00kf-9800000000-314e270d78e7a9ec16a9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophol 10V, Positive-QTOF	splash10-01ox-0900000000-ae84153e5d93042b79c8	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophol 20V, Positive-QTOF	splash10-0006-0900000000-b04d1b793a892b605239	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophol 40V, Positive-QTOF	splash10-014l-1900000000-eceb6c67d77a5dddf240	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophol 10V, Negative-QTOF	splash10-03di-0900000000-bfeeeabc14ffd14b537e	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophol 20V, Negative-QTOF	splash10-01q9-0900000000-e45fe37e44b99ede037e	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tryptophol 40V, Negative-QTOF	splash10-014l-2900000000-84aa43c0f5ccfd6511bb	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	31235863	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Tryptophol

METLIN ID

6932

PubChem Compound

10685

PDB ID

Not Available

ChEBI ID

17890

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1295861

References

Synthesis Reference

Snyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Cornford EM, Crane PD, Braun LD, Bocash WD, Nyerges AM, Oldendorf WH: Reduction in brain glucose utilization rate after tryptophol (3-indole ethanol) treatment. J Neurochem. 1981 May;36(5):1758-65. [PubMed:7241135 ]
Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]
Schirmer M, Smeekens SP, Vlamakis H, Jaeger M, Oosting M, Franzosa EA, Ter Horst R, Jansen T, Jacobs L, Bonder MJ, Kurilshikov A, Fu J, Joosten LAB, Zhernakova A, Huttenhower C, Wijmenga C, Netea MG, Xavier RJ: Linking the Human Gut Microbiome to Inflammatory Cytokine Production Capacity. Cell. 2016 Nov 3;167(4):1125-1136.e8. doi: 10.1016/j.cell.2016.10.020. [PubMed:27814509 ]

Showing metabocard for Tryptophol (HMDB0003447)

MOL for HMDB0003447 (Tryptophol)

3D MOL for HMDB0003447 (Tryptophol)

3D SDF for HMDB0003447 (Tryptophol)

3D-SDF for HMDB0003447 (Tryptophol)

PDB for HMDB0003447 (Tryptophol)

3D PDB for HMDB0003447 (Tryptophol)

SMILES for HMDB0003447 (Tryptophol)

INCHI for HMDB0003447 (Tryptophol)

Structure for HMDB0003447 (Tryptophol)

3D Structure for HMDB0003447 (Tryptophol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra