NP-MRD: Showing NP-Card for Tryptophanol (NP0000600)

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Record Information

Version

1.0

Created at

2006-08-12 21:10:36 UTC

Updated at

2021-08-19 23:58:14 UTC

NP-MRD ID

NP0000600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tryptophanol

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


  Mrv1652306242117433D          

 23 24  0  0  0  0            999 V2000
    3.3958    0.7068    0.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1055   -0.4710   -0.3037 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7375   -0.3845   -0.9665 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7021   -0.1617    0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562   -0.0377    1.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    0.1575    2.0046 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023    0.1660    1.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650    0.3201    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4210    0.2867   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7346    0.0873   -1.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -0.0714   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -0.0323   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    1.4418   -0.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0611   -1.3102    0.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8774   -0.6795   -1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979    0.4175   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5796   -1.3406   -1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066   -0.0922    1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5951    0.2888    3.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1606    0.4736    1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5151    0.4133   -0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753    0.0514   -2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -0.2296   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
  1 13  1  0  0  0  0
  2 14  1  0  0  0  0
  2 15  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  5 18  1  0  0  0  0
  6 19  1  0  0  0  0
  8 20  1  0  0  0  0
  9 21  1  0  0  0  0
 10 22  1  0  0  0  0
 11 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12

> <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

> <FORMULA>
C10H11NO

> <MOLECULAR_WEIGHT>
161.2004

> <EXACT_MASS>
161.084063979

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.87526502062822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1H-indol-3-yl)ethan-1-ol

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.5933192466666666

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.392512752772014

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.796075232386734

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4393148808629768

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
48.71540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tryptophol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       3.396   0.707   0.377  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.106  -0.471  -0.304  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.738  -0.385  -0.967  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.702  -0.162   0.058  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.856  -0.038   1.429  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.345   0.158   2.005  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.302   0.166   1.036  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.665   0.320   1.035  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.421   0.287  -0.119  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.735   0.087  -1.300  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.371  -0.071  -1.342  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.651  -0.032  -0.172  0.00  0.00           C+0
HETATM   13  H   UNK     0       2.943   1.442  -0.140  0.00  0.00           H+0
HETATM   14  H   UNK     0       3.061  -1.310   0.416  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.877  -0.680  -1.083  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.798   0.418  -1.724  0.00  0.00           H+0
HETATM   17  H   UNK     0       1.580  -1.341  -1.518  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.807  -0.092   1.944  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.595   0.289   3.004  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.161   0.474   1.980  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.515   0.413  -0.092  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.275   0.051  -2.242  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.826  -0.230  -2.279  0.00  0.00           H+0
CONECT    1    2   13                                                       
CONECT    2    1    3   14   15                                             
CONECT    3    2    4   16   17                                             
CONECT    4    3    5   12                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11    4    7                                                  
CONECT   13    1                                                            
CONECT   14    2                                                            
CONECT   15    2                                                            
CONECT   16    3                                                            
CONECT   17    3                                                            
CONECT   18    5                                                            
CONECT   19    6                                                            
CONECT   20    8                                                            
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

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
3-(2-Hydroxyethyl)-1H-indole	HMDB
3-(Β-hydroxyethyl)indole	HMDB
3-Indole ethanol	HMDB
Β-(3-indole)ethanol	HMDB
Tryptophol	HMDB, KEGG

Chemical Formula

C₁₀H₁₁NO

Average Mass

161.2004 Da

Monoisotopic Mass

161.08406 Da

IUPAC Name

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

Traditional Name

tryptophol

CAS Registry Number

526-55-6

SMILES

[H]OC([H])([H])C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Balansia epichloe	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cucumis sativus	KNApSAcK Database	22123792
Cucumis sativus L.	FooDB	KNAPSACK
Curvularia nodulosa	LOTUS Database	35616633
Dalbergia dolichopetala	KNApSAcK Database	22123792
Desmanthus illinoensis	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Epichloe festucae	LOTUS Database	35616633
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Grosmannia crassivaginata	LOTUS Database	35616633
Helianthus annuus	KNApSAcK Database	22123792
Helianthus annuus L.	FooDB	KNAPSACK
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Luffariella geometrica	-	KNApSAcK
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mucor moelleri	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Paraphaeosphaeria minitans	LOTUS Database	35616633
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phizobium	-	KNApSAcK
Picea abies	KNApSAcK Database	22123792
Pinus sylvestris	KNApSAcK Database	22123792
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Vitis	FooDB	KNAPSACK
Vitis spp.	KNApSAcK Database	22123792
Vitis vinifera	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Drechslera nodulosum	KNApSAcK Database	22123792
Hansenula henricii	KNApSAcK Database	22123792
Phycomyces blakesleeanus	KNApSAcK Database	22123792
Saccharomyces cerevisiae	KNApSAcK Database	22123792
Streptomyces atroolivaceus	KNApSAcK Database	22123792
Streptomyces mutabilis	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0003447

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1295861

References

General References

Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
Takahashi S, Godse DD, Naqvi A, Warsh JJ, Stancer HC: 5-Hydroxytryptophol in human cerebrospinal fluid: quantitative determination by gas chromatography-mass spectrometry using a deuterated internal standard. Clin Chim Acta. 1978 Mar 1;84(1-2):55-62. [PubMed:639316 ]
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. [PubMed:2342128 ]
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 NP-Card for Tryptophanol (NP0000600)

MOL for NP0000600 (Tryptophanol)

3D MOL for NP0000600 (Tryptophanol)

3D SDF for NP0000600 (Tryptophanol)

3D-SDF for NP0000600 (Tryptophanol)

PDB for NP0000600 (Tryptophanol)

3D PDB for NP0000600 (Tryptophanol)

SMILES for NP0000600 (Tryptophanol)

INCHI for NP0000600 (Tryptophanol)

Structure for NP0000600 (Tryptophanol)

3D Structure for NP0000600 (Tryptophanol)