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(2R,3R)-2-hydroxy-3-methylpentanoic acid

PubChem CID
10796774
Structure
(2R,3R)-2-hydroxy-3-methylpentanoic acid_small.png
(2R,3R)-2-hydroxy-3-methylpentanoic acid_3D_Structure.png
Molecular Formula
Synonyms
  • (2R,3R)-2-hydroxy-3-methylpentanoic acid
  • 86540-81-0
  • D-Isoleucic acid
  • Pentanoic acid, 2-hydroxy-3-methyl-, (2R,3R)-
  • isoleucic acid
Molecular Weight
132.16 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2006-10-26
  • Modify:
    2025-01-18
Description
(2R,3R)-2-hydroxy-3-methylpentanoic acid is a (2R)-2-hydroxy monocarboxylic acid and a 2-hydroxy-3-methylpentanoic acid. It is a conjugate acid of a (2R,3R)-2-hydroxy-3-methylpentanoate.
(2R,3R)-2-hydroxy-3-methylpentanoic acid has been reported in Vitis vinifera and Saccharomyces cerevisiae with data available.
2-Hydroxy-3-methylvalerate is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2R,3R)-2-hydroxy-3-methylpentanoic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R)-2-hydroxy-3-methylpentanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

RILPIWOPNGRASR-RFZPGFLSSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC[C@@H](C)[C@H](C(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H12O3
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

59653-35-9
86540-81-0
488-15-3

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 Lipid Maps ID (LM_ID)

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
132.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
0.9
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
132.078644241 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
132.078644241 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
57.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
9
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
100
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
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 2011.04.04)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.3 Chemical Classes

3.3.1 Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 3
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

41.00193 100

43.01806 67.40

Thumbnail
Thumbnail
2 of 3
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

85.06566 100

131.07056 8.90

69.03373 7.20

43.01913 3.80

41.03895 3.40

Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
131.0713682
Instrument
Agilent qTOF 6545
Instrument Type
LC-ESI-QTOF
Ionization Mode
negative
Collision Energy
40 eV
Top 5 Peaks

41.00193 100

43.01806 67.40

41.03621 5.20

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
131.0713682
Instrument
Agilent qTOF 6545
Instrument Type
LC-ESI-QTOF
Ionization Mode
negative
Collision Energy
10 eV
Top 5 Peaks

85.06573 100

131.07153 66.60

44.99745 6.20

85.10078 3.40

85.11488 3.10

Thumbnail
Thumbnail

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Extracellular
  • Membrane

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]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

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

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2A (100%)

STOT SE 3 (100%)

10 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 22148915, 19006102, 23940645, 24424155, 20156336, 19678709, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Maple syrup urine disease
References

PubMed: 6422161, 12101068, 10508118, 10472531, 11978597, 19551947, 10234605, 23430924, 18088602

Peritoneal dialysis in maple-syrup-urine disease: Studies on branched-chain amino and keto acids. Eur J Pediatr (1980) 134: 57. https://doi.org/10.1007/BF00442404

MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart
Disease
Dihydrolipoamide Dehydrogenase Deficiency
References
Disease
Tooth Decay
References
PubMed: 31026179

11 Literature

11.1 Consolidated References

11.2 Chemical Co-Occurrences in Literature

11.3 Chemical-Gene Co-Occurrences in Literature

11.4 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 Pathways

14 Taxonomy

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

15 Classification

15.1 ChEBI Ontology

15.2 LIPID MAPS Classification

15.3 ChemIDplus

15.4 UN GHS Classification

15.5 EPA DSSTox Classification

15.6 LOTUS Tree

15.7 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. ChEBI
    (2R,3R)-2-hydroxy-3-methylpentanoic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:89228
  2. 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/
    (2R,3R)-2-hydroxy-3-methylpentanoic acid
    https://www.wikidata.org/wiki/Q27161414
  3. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
    2-Hydroxy-3-methylvalerate
    https://www.ymdb.ca/compounds/YMDB01571
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA DSSTox
    (2R,3R)-2-Hydroxy-3-methylpentanoic acid
    https://comptox.epa.gov/dashboard/DTXSID601347302
    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. Human Metabolome Database (HMDB)
    LICENSE
    HMDB 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 (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    2-Hydroxy-3-methylpentanoic acid
    http://www.hmdb.ca/metabolites/HMDB0000317
  9. 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
    2-Hydroxy-3-methylpentanoic acid
    https://foodb.ca/compounds/FDB021944
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  12. Natural Product Activity and Species Source (NPASS)
  13. 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
  14. Metabolomics Workbench
  15. Wikidata
    (2R,3R)-2-hydroxy-3-methylpentanoic acid
    https://www.wikidata.org/wiki/Q27161414
  16. PubChem
  17. GHS Classification (UNECE)
  18. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  19. PATENTSCOPE (WIPO)
CONTENTS