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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-08-02 20:47:26 UTC

Update Date

2022-03-07 03:18:01 UTC

HMDB ID

HMDB0094716

Secondary Accession Numbers

HMDB94716

Metabolite Identification

Common Name

hydroxybutyrylglycine

Description

hydroxybutyrylglycine belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on hydroxybutyrylglycine.

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

C₆H₁₁NO₄

Average Molecular Weight

161.157

Monoisotopic Molecular Weight

161.068807838

IUPAC Name

2-[(1,4-dihydroxybutylidene)amino]acetic acid

Traditional Name

[(1,4-dihydroxybutylidene)amino]acetic acid

CAS Registry Number

Not Available

SMILES

OCCCC(O)=NCC(O)=O

InChI Identifier

InChI=1S/C6H11NO4/c8-3-1-2-5(9)7-4-6(10)11/h8H,1-4H2,(H,7,9)(H,10,11)

InChI Key

WABAQBDHJGJDEH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen 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-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 20971021)

Source

Exogenous

Exogenous (HMDB: HMDB0094716)

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
logP	-0.97	ALOGPS
logP	-0.8	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	1.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.12 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.13 m³·mol⁻¹	ChemAxon
Polarizability	15.79 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]+	135.496	31661259
DarkChem	[M-H]-	131.755	31661259
DeepCCS	[M+H]+	130.557	30932474
DeepCCS	[M-H]-	127.536	30932474
DeepCCS	[M-2H]-	164.092	30932474
DeepCCS	[M+Na]+	139.27	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.8	32859911
AllCCS	[M+NH4]+	139.2	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	133.7	32859911
AllCCS	[M+Na-2H]-	135.6	32859911
AllCCS	[M+HCOO]-	137.7	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.	1.52 minutes	32390414
Predicted by Siyang on May 30, 2022	8.4924 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.04 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	598.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	57.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	53.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	253.5 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	231.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	567.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	549.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	54.9 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	758.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	179.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	174.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	554.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	316.3 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	276.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
hydroxybutyrylglycine	OCCCC(O)=NCC(O)=O	2646.8	Standard polar	33892256
hydroxybutyrylglycine	OCCCC(O)=NCC(O)=O	1437.9	Standard non polar	33892256
hydroxybutyrylglycine	OCCCC(O)=NCC(O)=O	1621.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
hydroxybutyrylglycine,1TMS,isomer #1	C[Si](C)(C)OCCCC(O)=NCC(=O)O	1668.7	Semi standard non polar	33892256
hydroxybutyrylglycine,1TMS,isomer #2	C[Si](C)(C)OC(CCCO)=NCC(=O)O	1672.1	Semi standard non polar	33892256
hydroxybutyrylglycine,1TMS,isomer #3	C[Si](C)(C)OC(=O)CN=C(O)CCCO	1652.5	Semi standard non polar	33892256
hydroxybutyrylglycine,2TMS,isomer #1	C[Si](C)(C)OCCCC(=NCC(=O)O)O[Si](C)(C)C	1729.5	Semi standard non polar	33892256
hydroxybutyrylglycine,2TMS,isomer #2	C[Si](C)(C)OCCCC(O)=NCC(=O)O[Si](C)(C)C	1719.2	Semi standard non polar	33892256
hydroxybutyrylglycine,2TMS,isomer #3	C[Si](C)(C)OC(=O)CN=C(CCCO)O[Si](C)(C)C	1713.5	Semi standard non polar	33892256
hydroxybutyrylglycine,3TMS,isomer #1	C[Si](C)(C)OCCCC(=NCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1765.4	Semi standard non polar	33892256
hydroxybutyrylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC(O)=NCC(=O)O	1908.8	Semi standard non polar	33892256
hydroxybutyrylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CCCO)=NCC(=O)O	1895.5	Semi standard non polar	33892256
hydroxybutyrylglycine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CN=C(O)CCCO	1860.6	Semi standard non polar	33892256
hydroxybutyrylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC(=NCC(=O)O)O[Si](C)(C)C(C)(C)C	2153.1	Semi standard non polar	33892256
hydroxybutyrylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCC(O)=NCC(=O)O[Si](C)(C)C(C)(C)C	2141.7	Semi standard non polar	33892256
hydroxybutyrylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CN=C(CCCO)O[Si](C)(C)C(C)(C)C	2100.1	Semi standard non polar	33892256
hydroxybutyrylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC(=NCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2312.2	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 - hydroxybutyrylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9100000000-eae5820085f97dc3e3ba	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - hydroxybutyrylglycine GC-MS (3 TMS) - 70eV, Positive	splash10-00di-9323000000-01263c2ce60b2bfc2119	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - hydroxybutyrylglycine 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 - hydroxybutyrylglycine 10V, Negative-QTOF	splash10-03di-1900000000-2f07e47175bbe1c8f702	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 20V, Negative-QTOF	splash10-03kc-5900000000-76326042d160145266d5	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 40V, Negative-QTOF	splash10-00dl-9000000000-b6ec587df209e104227f	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 10V, Positive-QTOF	splash10-00dl-9800000000-fefad75975933ce18198	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 20V, Positive-QTOF	splash10-00di-9100000000-011415ec521fd3477d15	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 40V, Positive-QTOF	splash10-0adi-9000000000-2a6f7178aa840da97419	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 10V, Negative-QTOF	splash10-00di-9100000000-7872fc6af4a5dd397845	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 20V, Negative-QTOF	splash10-00di-9100000000-d39c230df012f4a7ddb4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 40V, Negative-QTOF	splash10-0ab9-9000000000-296bdb4a386f9fbe4a18	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 10V, Positive-QTOF	splash10-03dl-4900000000-e7d37f1b123a8233f9ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 20V, Positive-QTOF	splash10-0fkd-9200000000-75466c83be24ba8cf6ab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - hydroxybutyrylglycine 40V, Positive-QTOF	splash10-05fr-9000000000-bbc0f28ba2460688c9dc	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)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (24-38years old)	Not Specified	Normal	20971021	details

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

7983259

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9807500

PDB ID

Not Available

ChEBI ID

Not Available

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 hydroxybutyrylglycine (HMDB0094716)

MOL for HMDB0094716 (hydroxybutyrylglycine)

3D MOL for HMDB0094716 (hydroxybutyrylglycine)

3D SDF for HMDB0094716 (hydroxybutyrylglycine)

3D-SDF for HMDB0094716 (hydroxybutyrylglycine)

PDB for HMDB0094716 (hydroxybutyrylglycine)

3D PDB for HMDB0094716 (hydroxybutyrylglycine)

SMILES for HMDB0094716 (hydroxybutyrylglycine)

INCHI for HMDB0094716 (hydroxybutyrylglycine)

Structure for HMDB0094716 (hydroxybutyrylglycine)

3D Structure for HMDB0094716 (hydroxybutyrylglycine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra