Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-05-18 14:04:04 UTC

Update Date

2023-02-21 17:18:01 UTC

HMDB ID

HMDB0013716

Secondary Accession Numbers

HMDB13716

Metabolite Identification

Common Name

Norvaline

Description

Norvaline is a non-proteinogenic branched-chain amino acid with the chemical formula C5H11NO2, isomeric with valine. It has previously been reported to be a natural component of an antifungal peptide of Bacillus subtilis. Norvaline and other modified branched chain amino acids have received attention in recent studies, as they appear to be incorporated in some recombinant proteins found in E. coli. This amino acid is often made synthetically.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-Norvaline	ChEBI
D-2-Aminovaleric acid	ChEBI
D-Ape	ChEBI
D-Norvaline	ChEBI
D-Nva	ChEBI
D-2-Aminopentanoic acid	Kegg
D-2-Aminovalerate	Generator
D-2-Aminopentanoate	Generator
(.+-.)-norvaline	HMDB
(.+/-.)-norvaline	HMDB
2-Amino-DL-valeric acid	HMDB
2-Aminopentanoic acids	HMDB
2-Aminovaleric acid	HMDB
2-Aminovaleric acids	HMDB
alpha -DL-Aminopentanoic acid	HMDB
alpha-Aminopentanoic acid	HMDB
alpha-Aminovaleric acid	HMDB
alpha-DL-Aminopentanoic acid	HMDB
DL-2-Aminopentanoic acid	HMDB
DL-alpha -Aminovaleric acid	HMDB
DL-alpha-Amino-N-valenic acid	HMDB
DL-alpha-Aminovaleric acid	HMDB
DL-Norvaline	HMDB
Norvaline (acd/name 4.0)	HMDB
Norvalines	HMDB

Chemical Formula

C₅H₁₁NO₂

Average Molecular Weight

117.1463

Monoisotopic Molecular Weight

117.078978601

IUPAC Name

(2R)-2-aminopentanoic acid

Traditional Name

D-(-)-norvaline

CAS Registry Number

760-78-1

SMILES

CCC[C@@H](N)C(O)=O

InChI Identifier

InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1

InChI Key

SNDPXSYFESPGGJ-SCSAIBSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

D-alpha-amino acids

Alternative Parents

Substituents

D-alpha-amino acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acid
Fatty acyl
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:28804 )
2-aminopentanoic acid (CHEBI:28804 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013716)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 27275383)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Cereal and cereal product

Cereal

Common buckwheat (FooDB: FOOD00079)

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	303 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	83.9 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	120.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002163

Predicted Molecular Properties

Property	Value	Source
Water Solubility	212 g/L	ALOGPS
logP	-2	ALOGPS
logP	-1.9	ChemAxon
logS	0.26	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	29.62 m³·mol⁻¹	ChemAxon
Polarizability	12.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.995	31661259
DarkChem	[M-H]-	122.158	31661259
DeepCCS	[M+H]+	123.636	30932474
DeepCCS	[M-H]-	120.425	30932474
DeepCCS	[M-2H]-	157.342	30932474
DeepCCS	[M+Na]+	132.277	30932474
AllCCS	[M+H]+	129.5	32859911
AllCCS	[M+H-H2O]+	125.3	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	128.4	32859911
AllCCS	[M+HCOO]-	132.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norvaline	CCC[C@@H](N)C(O)=O	1890.0	Standard polar	33892256
Norvaline	CCC[C@@H](N)C(O)=O	1054.2	Standard non polar	33892256
Norvaline	CCC[C@@H](N)C(O)=O	1288.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norvaline,1TMS,isomer #1	CCC[C@@H](N)C(=O)O[Si](C)(C)C	1116.3	Semi standard non polar	33892256
Norvaline,1TMS,isomer #2	CCC[C@@H](N[Si](C)(C)C)C(=O)O	1212.4	Semi standard non polar	33892256
Norvaline,2TMS,isomer #1	CCC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1249.5	Semi standard non polar	33892256
Norvaline,2TMS,isomer #1	CCC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1275.2	Standard non polar	33892256
Norvaline,2TMS,isomer #1	CCC[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1383.7	Standard polar	33892256
Norvaline,2TMS,isomer #2	CCC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1404.7	Semi standard non polar	33892256
Norvaline,2TMS,isomer #2	CCC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1309.2	Standard non polar	33892256
Norvaline,2TMS,isomer #2	CCC[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1549.2	Standard polar	33892256
Norvaline,3TMS,isomer #1	CCC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1454.7	Semi standard non polar	33892256
Norvaline,3TMS,isomer #1	CCC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1392.0	Standard non polar	33892256
Norvaline,3TMS,isomer #1	CCC[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1382.8	Standard polar	33892256
Norvaline,1TBDMS,isomer #1	CCC[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1334.4	Semi standard non polar	33892256
Norvaline,1TBDMS,isomer #2	CCC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1442.3	Semi standard non polar	33892256
Norvaline,2TBDMS,isomer #1	CCC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1686.6	Semi standard non polar	33892256
Norvaline,2TBDMS,isomer #1	CCC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1673.8	Standard non polar	33892256
Norvaline,2TBDMS,isomer #1	CCC[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1683.7	Standard polar	33892256
Norvaline,2TBDMS,isomer #2	CCC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1813.4	Semi standard non polar	33892256
Norvaline,2TBDMS,isomer #2	CCC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1729.8	Standard non polar	33892256
Norvaline,2TBDMS,isomer #2	CCC[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1760.1	Standard polar	33892256
Norvaline,3TBDMS,isomer #1	CCC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2109.3	Semi standard non polar	33892256
Norvaline,3TBDMS,isomer #1	CCC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2005.5	Standard non polar	33892256
Norvaline,3TBDMS,isomer #1	CCC[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1809.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norvaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-9000000000-463db7a51bc96eebb0fc	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norvaline GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9400000000-0b48fca984c779b8df56	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norvaline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norvaline 10V, Positive-QTOF	splash10-00di-9000000000-0ecffe5b84a5ea6a4bbf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norvaline 20V, Positive-QTOF	splash10-00di-9000000000-0d904272d7c67068d5e3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norvaline 40V, Positive-QTOF	splash10-0006-9000000000-3ce17b37eda42107125e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 10V, Positive-QTOF	splash10-00xr-9600000000-2f35fd2b5cbb04e2b774	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 20V, Positive-QTOF	splash10-00di-9000000000-37a67ae027626a67be6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 40V, Positive-QTOF	splash10-0006-9000000000-b4ab8ccafd1a67b71b08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 10V, Negative-QTOF	splash10-014i-3900000000-13e844a45f41a4d61e38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 20V, Negative-QTOF	splash10-014i-9600000000-b57d7c5c40031d4c9b27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 40V, Negative-QTOF	splash10-00di-9000000000-554519282162f7a95cd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 10V, Negative-QTOF	splash10-014i-0900000000-92555825d99a6154218c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 20V, Negative-QTOF	splash10-014i-3900000000-5c84a32ca88953c60c8c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 40V, Negative-QTOF	splash10-0006-9000000000-5a2e317c643a4b5b9221	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 10V, Positive-QTOF	splash10-05fr-9000000000-0accde1cfaabd04695a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 20V, Positive-QTOF	splash10-0a4i-9000000000-eceb07db0f395719c1cc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norvaline 40V, Positive-QTOF	splash10-0abc-9000000000-dd0b01b18824186f0daf	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	0.02 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00018307

Chemspider ID

388660

KEGG Compound ID

C01799

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norvaline

METLIN ID

Not Available

PubChem Compound

439575

PDB ID

Not Available

ChEBI ID

28804

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Norvaline (HMDB0013716)

MOL for HMDB0013716 (Norvaline)

3D MOL for HMDB0013716 (Norvaline)

3D SDF for HMDB0013716 (Norvaline)

3D-SDF for HMDB0013716 (Norvaline)

PDB for HMDB0013716 (Norvaline)

3D PDB for HMDB0013716 (Norvaline)

SMILES for HMDB0013716 (Norvaline)

INCHI for HMDB0013716 (Norvaline)

Structure for HMDB0013716 (Norvaline)

3D Structure for HMDB0013716 (Norvaline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra