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(2S,3S)-2-ammonio-3-methylpentanoate

PubChem CID
7043901
Structure
(2S,3S)-2-ammonio-3-methylpentanoate_small.png
(2S,3S)-2-ammonio-3-methylpentanoate_3D_Structure.png
(2S,3S)-2-ammonio-3-methylpentanoate__Crystal_Structure.png
Molecular Formula
Synonyms
  • (2S,3S)-2-ammonio-3-methylpentanoate
  • (2S,3S)-2-azaniumyl-3-methylpentanoate
  • L-isoleucine zwitterion
  • 3f6g
  • 3f6h
Molecular Weight
131.17 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-07-29
  • Modify:
    2025-01-18
Description
L-isoleucine zwitterion is an L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of L-isoleucine; major species at pH 7.3. It is a tautomer of a L-isoleucine.
L-Isoleucine is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2S,3S)-2-ammonio-3-methylpentanoate.png

1.2 3D Conformer

1.3 Crystal Structures

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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-Ile-OH
Sequence
I
PLN
H-I-OH
HELM
PEPTIDE1{I}$$$$
IUPAC
L-isoleucine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2S,3S)-2-azaniumyl-3-methylpentanoate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

AGPKZVBTJJNPAG-WHFBIAKZSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

CC[C@H](C)[C@@H](C(=O)[O-])[NH3+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C6H13NO2
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 CAS

3.3.3 ChEBI ID

3.3.4 HMDB ID

3.3.5 Lipid Maps ID (LM_ID)

3.3.6 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
131.17 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3
Property Value
-1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
131.094628657 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
131.094628657 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
67.8 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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
97.7
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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)

4.2 Experimental Properties

4.2.1 Physical Description

Solid

4.2.2 Melting Point

285.5 °C

4.2.3 Solubility

35 mg/mL
Human Metabolome Project

4.2.4 LogP

-1.70
HANSCH,C ET AL. (1995)

4.3 Chemical Classes

4.3.1 Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110]

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 1H NMR Spectra

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Spectra ID
Instrument Type
Varian
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
1.98:6.12, 1.96:6.13, 0.99:96.96, 1.49:1.69, 1.00:100.00, 1.24:6.89, 2.00:0.99, 1.27:6.85, 1.22:5.57, 1.97:7.17, 1.94:2.08, 1.47:6.60, 1.47:6.61, 1.99:2.03, 1.21:1.89, 1.45:7.65, 0.91:44.10, 0.94:50.89, 1.25:7.29, 1.97:7.52, 1.43:2.73, 1.96:7.22, 1.28:1.99, 1.99:3.48, 0.93:99.36, 1.48:5.44, 1.26:7.34, 1.46:9.26, 1.96:6.06, 3.66:34.77, 1.97:7.62, 1.25:7.87, 1.44:6.71, 1.98:5.77, 1.48:2.15, 1.26:8.61, 1.42:2.16, 1.95:3.55, 1.23:6.76, 3.66:34.21, 1.94:1.03, 1.44:7.79
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Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.1.2 13C NMR Spectra

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Spectra ID
Instrument Type
Bruker
Frequency
125 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
27.10:85.27, 13.75:79.29, 176.82:26.12, 38.60:88.43, -0.00:6.00, 17.35:80.47, 62.43:68.97
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Spectra ID
Frequency
400 MHz
Solvent
H2O
Shifts [ppm]
62.43, 17.35, 38.60, 176.82, 27.10, 13.75
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5.2 2D NMR Spectra

5.2.1 1H-1H NMR Spectra

2D NMR Spectra Type
1H-1H TOCSY
Spectra ID
Shifts [ppm] (F2:F1)
1.97:0.93, 1.25:0.91, 1.46:0.93, 0.94:1.28, 0.94:1.27, 3.67:1.02, 0.70:1.01, 1.15:1.15, 1.25:0.95, 1.25:1.48, 0.94:1.23, 0.93:1.48, 0.93:1.46, 1.46:0.99, 1.46:1.25, 1.46:1.29, 1.97:0.99, 1.98:0.95, 1.00:0.99, 0.93:0.95, 1.46:1.27, 1.25:1.24, 1.46:1.22, 1.97:1.48, 0.98:1.27, 1.97:0.91, 1.46:0.95, 1.46:0.91, 1.25:1.45, 1.25:1.46, 0.99:1.97, 1.97:1.45, 3.67:3.66, 1.98:1.46, 1.46:3.66, 1.98:1.27, 1.07:1.08, 1.00:1.01, 3.84:3.84, 0.69:0.99, 0.93:1.20, 0.93:0.91, 0.94:1.25, 1.97:3.66, 1.98:1.97, 1.25:1.25, 0.98:1.22, 1.97:1.01, 1.46:1.01, 1.46:1.97, 0.93:0.93, 1.46:1.45, 1.25:1.97, 0.77:0.77, 3.67:1.97, 1.98:1.29, 1.25:3.66, 0.93:1.31, 0.84:0.83, 0.84:0.85, 1.26:1.27, 1.26:1.29, 1.16:1.17, 1.00:3.66, 1.46:1.46, 1.97:1.22, 1.97:1.25, 0.93:1.45, 1.25:1.22
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5.2.2 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
0.93:13.91:0.08, 0.99:17.37:0.10, 1.25:27.25:0.28, 1.45:27.00:0.31, 1.96:38.69:0.37, 3.65:62.52:1.00
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5.3 Mass Spectrometry

5.3.1 GC-MS

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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

158.15 100

218.1 20.02

159.2 14.14

147.15 10.81

100.1 8.88

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Notes
instrument=GCMS-2010 Plus, Shimadzu
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Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

158.0 100

218.0 47.65

147.0 31.63

100.0 29.13

232.0 13.31

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Notes
instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies

5.3.2 MS-MS

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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

86.09078 100

69.06478 96.70

44.04484 52.60

41.03405 21.90

57.05235 16.10

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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

86.09962 100

69.07308 6.10

44.05154 4.30

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5.4 IR Spectra

5.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
KBr1
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A13699
Lot Number
A2271604
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Calbiochem, EMD Chemicals, Inc., an Affiliate of Merck KGaA, Darmstadt, Germany
Catalog Number
4160
Lot Number
605581
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A13699
Lot Number
A2271604
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.5 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A13699
Lot Number
A2271604
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Calbiochem, EMD Chemicals, Inc., an Affiliate of Merck KGaA, Darmstadt, Germany
Catalog Number
4160
Lot Number
605581
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
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7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Tissue Locations

  • All Tissues
  • Placenta
  • Prostate

8.1.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Mitochondria

8.1.3 Metabolite Pathways

8.2 Biochemical Reactions

9 Associated Disorders and Diseases

Disease
Heart failure
References
Disease
Maple syrup urine disease
References

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

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

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

Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 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
Early preeclampsia
References
PubMed: 22494326
Disease
Pregnancy
References

PubMed: 3252730, 663967, 12833386, 2994907, 17704099, 12698507, 17061063, 16925883, 22420377, 18059417, 22494326, 23159745, 23313728, 23535240, 24704061

The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.

Disease
Saccharopinuria
References
PubMed: 5018656
Disease
Dihydrolipoamide Dehydrogenase Deficiency
References
Disease
Branched-chain Keto Acid Dehydrogenase Kinase Deficiency
References
PubMed: 22956686
Disease
Lipoyltransferase 1 Deficiency
References
PubMed: 24341803
Disease
Leukemia
References
Disease
Irritable bowel syndrome
References
Disease
Perillyl alcohol administration for cancer treatment
References
Disease
Pancreatic cancer
References
Disease
Periodontal disease
References
PubMed: 20300169
Disease
Frontotemporal dementia
References
PubMed: 23857558
Disease
Lewy body disease
References
PubMed: 23857558
Disease
Attachment loss
References
PubMed: 31026179
Disease
Missing teeth
References
PubMed: 31026179
Disease
Periodontal Probing Depth
References
PubMed: 31026179
Disease
Autosomal dominant polycystic kidney disease
References
Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

10 Literature

10.1 Consolidated References

10.2 Thieme References

10.3 Chemical Co-Occurrences in Literature

10.4 Chemical-Gene Co-Occurrences in Literature

10.5 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Chemical Co-Occurrences in Patents

11.2 Chemical-Disease Co-Occurrences in Patents

11.3 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Pathways

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

15 Classification

15.1 ChEBI Ontology

15.2 LIPID MAPS Classification

15.3 LOTUS Tree

16 Information Sources

  1. 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/
  2. 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
  3. ChEBI
  4. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  5. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  6. The Cambridge Structural Database
  7. SpectraBase
  8. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  9. Natural Product Activity and Species Source (NPASS)
  10. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  11. 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/
  12. Wikidata
  13. PubChem
  14. 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/
CONTENTS