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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-08-01 02:19:15 UTC

Update Date

2022-03-07 03:18:00 UTC

HMDB ID

HMDB0094698

Secondary Accession Numbers

HMDB94698

Metabolite Identification

Common Name

N-Propionylalanine

Description

N-propionylalanine is classified as a member of the n-acyl-l-alpha-amino acids. N-acyl-L-alpha-amino acids are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-propionylalanine is considered to be a slightly soluble (in water) and a weak acidic compound. N-propionylalanine can be found in humans.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₁₁NO₃

Average Molecular Weight

145.158

Monoisotopic Molecular Weight

145.073893218

IUPAC Name

(2S)-2-[(1-hydroxypropylidene)amino]propanoic acid

Traditional Name

(2S)-2-[(1-hydroxypropylidene)amino]propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H11NO3/c1-3-5(8)7-4(2)6(9)10/h4H,3H2,1-2H3,(H,7,8)(H,9,10)/t4-/m0/s1

InChI Key

INPGLFHHFHOGRM-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-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

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Alanine or derivatives
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

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
logP	-0.07	ALOGPS
logP	0.76	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	1.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	35.09 m³·mol⁻¹	ChemAxon
Polarizability	14.55 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]+	132.566	31661259
DarkChem	[M-H]-	128.549	31661259
DeepCCS	[M+H]+	129.594	30932474
DeepCCS	[M-H]-	126.743	30932474
DeepCCS	[M-2H]-	163.096	30932474
DeepCCS	[M+Na]+	138.348	30932474
AllCCS	[M+H]+	135.7	32859911
AllCCS	[M+H-H2O]+	131.8	32859911
AllCCS	[M+NH4]+	139.4	32859911
AllCCS	[M+Na]+	140.4	32859911
AllCCS	[M-H]-	130.9	32859911
AllCCS	[M+Na-2H]-	133.3	32859911
AllCCS	[M+HCOO]-	136.0	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.	1.85 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5021 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.77 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	926.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	75.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	260.0 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	285.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	613.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	194.6 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	792.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	523.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	273.5 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	194.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Propionylalanine	[H][C@@](C)(N=C(O)CC)C(O)=O	2213.2	Standard polar	33892256
N-Propionylalanine	[H][C@@](C)(N=C(O)CC)C(O)=O	1201.6	Standard non polar	33892256
N-Propionylalanine	[H][C@@](C)(N=C(O)CC)C(O)=O	1297.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Propionylalanine,1TMS,isomer #1	CCC(=N[C@@H](C)C(=O)O)O[Si](C)(C)C	1358.1	Semi standard non polar	33892256
N-Propionylalanine,1TMS,isomer #2	CCC(O)=N[C@@H](C)C(=O)O[Si](C)(C)C	1292.7	Semi standard non polar	33892256
N-Propionylalanine,2TMS,isomer #1	CCC(=N[C@@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1402.5	Semi standard non polar	33892256
N-Propionylalanine,1TBDMS,isomer #1	CCC(=N[C@@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C	1583.3	Semi standard non polar	33892256
N-Propionylalanine,1TBDMS,isomer #2	CCC(O)=N[C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C	1504.2	Semi standard non polar	33892256
N-Propionylalanine,2TBDMS,isomer #1	CCC(=N[C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1819.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Propionylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9100000000-7e84e478ada3dabbc499	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Propionylalanine GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9530000000-c836ce6bd99bf7992bd4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Propionylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Propionylalanine 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-Propionylalanine 10V, Negative-QTOF	splash10-0006-1900000000-c347f7855e988dbdb218	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 20V, Negative-QTOF	splash10-05bo-9700000000-18618bb0580ce131cfc7	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 40V, Negative-QTOF	splash10-059l-9000000000-d490330332d6769a67bf	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 10V, Positive-QTOF	splash10-0f9b-4900000000-488aefaf6939a3dce736	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 20V, Positive-QTOF	splash10-0006-9200000000-2c4910c0e380cb89ba2b	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 40V, Positive-QTOF	splash10-0006-9000000000-b5c2607bd7e217d34790	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 10V, Positive-QTOF	splash10-0f6x-9400000000-92313a1f91992f2f4a3d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 20V, Positive-QTOF	splash10-006x-9000000000-db1fa54abca6d8871fc4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 40V, Positive-QTOF	splash10-0006-9000000000-a959d55148fc2ebba6b4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 10V, Negative-QTOF	splash10-000i-9000000000-a55e01b088458272bd26	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 20V, Negative-QTOF	splash10-000i-9000000000-ea87183130c8c29e05f6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Propionylalanine 40V, Negative-QTOF	splash10-0006-9000000000-f48be32e411042ce95d7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	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	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
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

Not Available

Chemspider ID

18500631

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22788191

PDB ID

Not Available

ChEBI ID

192720

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 N-Propionylalanine (HMDB0094698)

MOL for HMDB0094698 (N-Propionylalanine)

3D MOL for HMDB0094698 (N-Propionylalanine)

3D SDF for HMDB0094698 (N-Propionylalanine)

3D-SDF for HMDB0094698 (N-Propionylalanine)

PDB for HMDB0094698 (N-Propionylalanine)

3D PDB for HMDB0094698 (N-Propionylalanine)

SMILES for HMDB0094698 (N-Propionylalanine)

INCHI for HMDB0094698 (N-Propionylalanine)

Structure for HMDB0094698 (N-Propionylalanine)

3D Structure for HMDB0094698 (N-Propionylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra