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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-04-16 20:46:51 UTC

Update Date

2023-02-21 17:30:26 UTC

HMDB ID

HMDB0061716

Secondary Accession Numbers

HMDB61716

Metabolite Identification

Common Name

N-methylvaline

Description

N-methylvaline, also known as maval, belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-methylvaline is a very strong basic compound (based on its pKa). An optically active form of N-methylvaline having L-configuration.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-3-Methyl-2-(methylamino)butanoic acid	ChEBI
MaVal	ChEBI
Methylvaline	ChEBI
(2S)-3-Methyl-2-(methylamino)butanoate	Generator
MeVal	MeSH
3-Methyl-2-(methylamino)butanoic acid	MeSH
N-Methylvaline	ChEBI

Chemical Formula

C₆H₁₃NO₂

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

IUPAC Name

(2S)-3-methyl-2-(methylamino)butanoic acid

Traditional Name

(2S)-3-methyl-2-(methylamino)butanoic acid

CAS Registry Number

Not Available

SMILES

CN[C@@H](C(C)C)C(O)=O

InChI Identifier

InChI=1S/C6H13NO2/c1-4(2)5(7-3)6(8)9/h4-5,7H,1-3H3,(H,8,9)/t5-/m0/s1

InChI Key

AKCRVYNORCOYQT-YFKPBYRVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Valine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-methyl-L-alpha-amino acid (CHEBI:44212 )
N-methylvaline (CHEBI:44212 )

Ontology

Not Available

Exogenous (HMDB: HMDB0061716)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	119 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.7	ChemAxon
logS	-0.04	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	10.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.27 m³·mol⁻¹	ChemAxon
Polarizability	14.21 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]+	129.052	31661259
DarkChem	[M-H]-	125.795	31661259
DeepCCS	[M+H]+	128.825	30932474
DeepCCS	[M-H]-	124.996	30932474
DeepCCS	[M-2H]-	162.114	30932474
DeepCCS	[M+Na]+	137.524	30932474
AllCCS	[M+H]+	132.4	32859911
AllCCS	[M+H-H2O]+	128.3	32859911
AllCCS	[M+NH4]+	136.1	32859911
AllCCS	[M+Na]+	137.2	32859911
AllCCS	[M-H]-	129.2	32859911
AllCCS	[M+Na-2H]-	132.1	32859911
AllCCS	[M+HCOO]-	135.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.63 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5269 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	614.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	312.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	63.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	44.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	247.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	572.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	610.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	88.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	733.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	178.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	518.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	392.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	210.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-methylvaline	CN[C@@H](C(C)C)C(O)=O	1834.3	Standard polar	33892256
N-methylvaline	CN[C@@H](C(C)C)C(O)=O	1115.9	Standard non polar	33892256
N-methylvaline	CN[C@@H](C(C)C)C(O)=O	1083.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-methylvaline,1TMS,isomer #1	CN[C@H](C(=O)O[Si](C)(C)C)C(C)C	1092.2	Semi standard non polar	33892256
N-methylvaline,1TMS,isomer #2	CC(C)[C@@H](C(=O)O)N(C)[Si](C)(C)C	1232.4	Semi standard non polar	33892256
N-methylvaline,2TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	1263.9	Semi standard non polar	33892256
N-methylvaline,2TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	1216.0	Standard non polar	33892256
N-methylvaline,2TMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	1278.7	Standard polar	33892256
N-methylvaline,1TBDMS,isomer #1	CN[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C	1318.7	Semi standard non polar	33892256
N-methylvaline,1TBDMS,isomer #2	CC(C)[C@@H](C(=O)O)N(C)[Si](C)(C)C(C)(C)C	1463.8	Semi standard non polar	33892256
N-methylvaline,2TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	1723.4	Semi standard non polar	33892256
N-methylvaline,2TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	1678.7	Standard non polar	33892256
N-methylvaline,2TBDMS,isomer #1	CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	1604.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylvaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9000000000-2e57b58ca4ffbac54016	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylvaline GC-MS (1 TMS) - 70eV, Positive	splash10-000f-9100000000-9c606f603835e3793450	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylvaline 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 10V, Positive-QTOF	splash10-01qi-4900000000-1b1d110012b65191b57c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 20V, Positive-QTOF	splash10-000i-9300000000-ec3dce11c5e5d8e97e84	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 40V, Positive-QTOF	splash10-05fr-9000000000-95d5856ba1ad37111277	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 10V, Negative-QTOF	splash10-001r-4900000000-fbf697d8663079eed26f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 20V, Negative-QTOF	splash10-01qi-6900000000-282ec83fd2cc5d1dcf2f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 40V, Negative-QTOF	splash10-0083-9100000000-89b2da916a1d7a5f7ce8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 10V, Positive-QTOF	splash10-000i-9100000000-f4dd10fa5b3ccd6c3447	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 20V, Positive-QTOF	splash10-000i-9000000000-d28054a44ad67728c56b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 40V, Positive-QTOF	splash10-0006-9000000000-e247e1fc642339726414	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 10V, Negative-QTOF	splash10-001i-0900000000-06466c9190b13de8e4be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 20V, Negative-QTOF	splash10-001i-0900000000-1fad5f5fc44cfc94ec81	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylvaline 40V, Negative-QTOF	splash10-0006-9100000000-140dc49f5377093c54a7	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1059

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

444080

PDB ID

MVA

ChEBI ID

44212

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

Bader M, Lewalter J, Angerer J: Analysis of N-alkylated amino acids in human hemoglobin: evidence for elevated N-methylvaline levels in smokers. Int Arch Occup Environ Health. 1995;67(4):237-42. [PubMed:7591184 ]

Showing metabocard for N-methylvaline (HMDB0061716)

MOL for HMDB0061716 (N-methylvaline)

3D MOL for HMDB0061716 (N-methylvaline)

3D SDF for HMDB0061716 (N-methylvaline)

3D-SDF for HMDB0061716 (N-methylvaline)

PDB for HMDB0061716 (N-methylvaline)

3D PDB for HMDB0061716 (N-methylvaline)

SMILES for HMDB0061716 (N-methylvaline)

INCHI for HMDB0061716 (N-methylvaline)

Structure for HMDB0061716 (N-methylvaline)

3D Structure for HMDB0061716 (N-methylvaline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra