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Record Information
Version2.0
Created at2025-07-14 15:50:35 UTC
Updated at2025-09-22 01:00:52 UTC
NP-MRD IDNP0351316
Natural Product DOIhttps://doi.org/10.57994/4322
Secondary Accession NumbersNone
Natural Product Identification
Common NameTryptophol
DescriptionTryptophol, also known as 3-indoleethanol or IEA, 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. Tryptophol exists in all living species, ranging from bacteria to plants to humans. Tryptophol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Tryptophol was first documented in 1981 (PMID: 7241135). Based on a literature review a significant number of articles have been published on Tryptophol (PMID: 27814509) (PMID: 16664264) (PMID: 19842066) (PMID: 10856636) (PMID: 12499363) (PMID: 23413824).
Structure
Thumb
Synonyms
ValueSource
1H-Indole-3-ethanolChEBI
1H-Indolyl-3-ethanolChEBI
2-(indol-3-yl)EthanolChEBI
3-(2-Hydroxyethyl)indoleChEBI
Indole-3-ethanolChEBI
TryptophanolChEBI
2-(1H-indol-3-yl)EthanolHMDB
2-(3-Indolyl)ethanolHMDB
2-(3-IndolylethanolHMDB
3-(b-Hydroxyethyl)indoleHMDB
3-(beta-Hydroxyethyl)indoleHMDB
3-IndoleethanolHMDB
3-IndolylethanolHMDB
b-(3-Indole)ethanolHMDB
beta-(3-Indole)ethanolHMDB
beta-indol-3-YlethanolHMDB
DL-TryptophanolHMDB
IEAHMDB
Indole ethanolHMDB
IndoleethanolHMDB
3-(2-Hydroxyethyl)-1H-indoleHMDB
3-(Β-hydroxyethyl)indoleHMDB
3-Indole ethanolHMDB
Β-(3-indole)ethanolHMDB
TryptopholHMDB, KEGG
Chemical FormulaC10H11NO
Average Mass161.2004 Da
Monoisotopic Mass161.08406 Da
IUPAC Name2-(1H-indol-3-yl)ethan-1-ol
Traditional Nametryptophol
CAS Registry NumberNot Available
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 KeyMBBOMCVGYCRMEA-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)sanjeevan.chem@gmail.comUniversity of North TexasSanjeevan Rajendran2025-09-21View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)sanjeevan.chem@gmail.comUniversity of North TexasSanjeevan Rajendran2025-09-21View Spectrum
HMQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)sanjeevan.chem@gmail.comUniversity of North TexasSanjeevan Rajendran2025-09-21View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)sanjeevan.chem@gmail.comUniversity of North TexasSanjeevan Rajendran2025-09-21View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)sanjeevan.chem@gmail.comUniversity of North TexasSanjeevan Rajendran2025-09-21View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)sanjeevan.chem@gmail.comUniversity of North TexasSanjeevan Rajendran2025-09-21View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)sanjeevan.chem@gmail.comUniversity of North TexasSanjeevan Rajendran2025-09-21View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)rjm4kd@umsystem.eduSumner lab, University of MissouriRonald Myers2025-07-14View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)rjm4kd@umsystem.eduSumner lab, University of MissouriRonald Myers2025-07-14View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)rjm4kd@umsystem.eduSumner lab, University of MissouriRonald Myers2025-07-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)rjm4kd@umsystem.eduSumner lab, University of MissouriRonald Myers2025-07-14View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600.0 MHz, C2D6OS, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.0, C2D6OS, simulated)rjm4kd@umsystem.eduSumner lab, University of MissouriRonald Myers2025-07-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Colletotrichum spinosum
      Not Available
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.82ALOGPS
logP1.59ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)15.8ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.72 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003447
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030938
KNApSAcK IDC00000114
Chemspider ID10235
KEGG Compound IDC00955
BioCyc IDCPD-341
BiGG IDNot Available
Wikipedia LinkTryptophol
METLIN ID6932
PubChem Compound10685
PDB IDNot Available
ChEBI ID17890
Good Scents IDrw1295861
References
General References
  1. 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 ]
  2. 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 ]
  3. Lacan G, Magnus V, Simaga S, Iskric S, Hall PJ: Metabolism of tryptophol in higher and lower plants. Plant Physiol. 1985 Jul;78(3):447-54. doi: 10.1104/pp.78.3.447. [PubMed:16664264 ]
  4. Elleuch L, Shaaban M, Smaoui S, Mellouli L, Karray-Rebai I, Fourati-Ben Fguira L, Shaaban KA, Laatsch H: Bioactive secondary metabolites from a new terrestrial Streptomyces sp. TN262. Appl Biochem Biotechnol. 2010 Sep;162(2):579-93. doi: 10.1007/s12010-009-8808-4. Epub 2009 Oct 20. [PubMed:19842066 ]
  5. Erdoğan I I, Sener B, Higa T: Tryptophol, a plant auxin isolated from the marine sponge Ircinia spinulosa. Biochem Syst Ecol. 2000 Oct 1;28(8):793-794. doi: 10.1016/s0305-1978(99)00111-8. [PubMed:10856636 ]
  6. Dickinson JR, Salgado LE, Hewlins MJ: The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae. J Biol Chem. 2003 Mar 7;278(10):8028-34. doi: 10.1074/jbc.M211914200. Epub 2002 Dec 23. [PubMed:12499363 ]
  7. Zupan J, Avbelj M, Butinar B, Kosel J, Sergan M, Raspor P: Monitoring of quorum-sensing molecules during minifermentation studies in wine yeast. J Agric Food Chem. 2013 Mar 13;61(10):2496-505. doi: 10.1021/jf3051363. Epub 2013 Mar 5. [PubMed:23413824 ]
  8. Nazari F, Sulyok M, Yazdanpanah H, Kobarfard F, Krska R: A survey of mycotoxins in domestic rice in Iran by liquid chromatography tandem mass spectrometry. Toxicol Mech Methods. 2014 Jan;24(1):37-41. doi: 10.3109/15376516.2013.844752. Epub 2013 Oct 28. [PubMed:24032669 ]
  9. Sandberg G: Biosynthesis and metabolism of indole-3-ethanol and indole-3-acetic acid by Pinus sylvestris L. needles. Planta. 1984 Jul;161(5):398-403. doi: 10.1007/BF00394569. [PubMed:24253838 ]
  10. Eze F, Schoellhorn S, Grinffiel D, Chapman K, Rajendran S, Skellam E: Assessing the Biosynthetic Potential of the Bioherbicide Colletotrichum spinosum CBS 515.97: Discovery of 3"-Demethylthielavin M and Assorted Alkaloids. Chem Biodivers. 2025 Aug 14:e01247. doi: 10.1002/cbdv.202501247. [PubMed:40812239 ]
  11. DOI: 10.1002/cbdv.202501247
  12. PMID: 40812239