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Indole-3-lactic acid

PubChem CID
92904
Structure
Indole-3-lactic acid_small.png
Indole-3-lactic acid_3D_Structure.png
Molecular Formula
Synonyms
  • Indole-3-lactic acid
  • 1821-52-9
  • dl-Indole-3-lactic acid
  • 2-Hydroxy-3-(1H-indol-3-yl)propanoic acid
  • Indolelactic acid
Molecular Weight
205.21 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18
Description
3-(indol-3-yl)lactic acid is a hydroxy monocarboxylic acid that is lactic acid substituted by a 1H-indol-3-yl group at position 3. It is a metabolite of tryptophan. It has a role as a human metabolite. It is an indol-3-yl carboxylic acid and a hydroxy monocarboxylic acid. It is functionally related to a rac-lactic acid. It is a conjugate acid of a 3-(indol-3-yl)lactate.
Indole-3-lactic acid has been reported in Daphnia pulex, Agrobacterium tumefaciens, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Indole-3-lactic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxy-3-(1H-indol-3-yl)propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C11H11NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12-13H,5H2,(H,14,15)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

XGILAAMKEQUXLS-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C11H11NO3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

832-97-3

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 KEGG ID

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5-hydroxyindolepropionic acid
  • 5-iHIPA
  • indole-3-lactate
  • indole-3-lactic acid
  • indole-3-lactic acid, (+-)-isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
205.21 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
205.07389321 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
205.07389321 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
73.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
244
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Collision Cross Section

146.51 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

143.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 7
View All
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Leco Pegasus IV
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

130 100

131 10.71

147 9.91

103 5.01

259 3.60

Thumbnail
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2 of 7
View All
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Leco Pegasus IV
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

202 100

203 18.62

147 12.81

204 5.51

200 3.20

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4.2.2 MS-MS

1 of 2
NIST Number
1053338
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
206.0812
Total Peaks
9
m/z Top Peak
188.1
m/z 2nd Highest
160.1
m/z 3rd Highest
130.1
Thumbnail
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2 of 2
NIST Number
1053340
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M-H]-
Precursor m/z
204.0666
Total Peaks
10
m/z Top Peak
186.1
m/z 2nd Highest
158.1
m/z 3rd Highest
116.1
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4.2.3 LC-MS

1 of 4
View All
Authors
Evans A M, Mitchell M, DeHaven C D, Barrett T, Milgram E, Metabolon Inc.
Instrument
LTQ XL, Thermo Finnigan
Instrument Type
LC-ESI-IT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
40
Precursor m/z
206.1
Precursor Adduct
[M+H]+
Top 5 Peaks

188.1 999

160.1 651

130.1 70

189.1 53

118.1 44

Thumbnail
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License
CC BY-NC-ND
2 of 4
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
206.1
Instrument
LTQ XL, Thermo Finnigan
Instrument Type
LC-ESI-IT
Ionization
ESI
Ionization Mode
positive
Collision Energy
40
Top 5 Peaks

188.1 100

160.1 65.20

130.1 7

189.1 5.30

118.1 4.40

Thumbnail
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License
CC BY-NC-ND

4.2.4 Other MS

1 of 2
MS Category
Experimental
MS Type
Other
Precursor Type
M+H
Precursor m/z
206.081
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

178.086243 100

55.286194 20.60

55.310284 17.40

55.29089 16.14

55.305553 14.80

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2 of 2
MS Category
Experimental
MS Type
Other
Precursor Type
M-H2O+H
Precursor m/z
188.07
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

160.075577 100

56.048428 36.82

71.986649 23.94

56.065754 23.57

56.082729 23.12

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4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
I5508
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
I5508
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Biochemical Reactions

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statement Codes

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

9.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Wiley References

11.6 Chemical Co-Occurrences in Literature

11.7 Chemical-Gene Co-Occurrences in Literature

11.8 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

13.2 Pathways

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 ChEMBL Target Tree

16.5 UN GHS Classification

16.6 NORMAN Suspect List Exchange Classification

16.7 CCSBase Classification

16.8 EPA DSSTox Classification

16.9 The Natural Products Atlas Classification

16.10 LOTUS Tree

16.11 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  2. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  3. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  7. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  9. ChEBI
  10. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  11. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  12. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  15. KNApSAcK Species-Metabolite Database
  16. Natural Product Activity and Species Source (NPASS)
    2-Hydroxy-3-(1H-Indol-3-Yl)Propanoic Acid
    https://bidd.group/NPASS/compound.php?compoundID=NPC315555
  17. The Natural Products Atlas
    LICENSE
    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  18. MassBank Europe
  19. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  20. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    1H-Indole-3-propanoic acid, .alpha.-hydroxy-
    http://www.nist.gov/srd/nist1a.cfm
  21. SpectraBase
  22. Metabolomics Workbench
  23. Springer Nature
  24. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  25. Wikidata
  26. Wiley
  27. PubChem
  28. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  29. GHS Classification (UNECE)
  30. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  31. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  32. PATENTSCOPE (WIPO)
  33. NCBI
CONTENTS