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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-08 21:44:18 UTC

Update Date

2021-09-14 15:44:57 UTC

HMDB ID

HMDB0029230

Secondary Accession Numbers

HMDB29230

Metabolite Identification

Common Name

4-Hydroxystachydrine

Description

4-Hydroxystachydrine belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 4-Hydroxystachydrine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-hydroxystachydrine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Hydroxystachydrine.

Structure

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

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0      -3.300  -2.760   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      -4.546  -3.665   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.070  -5.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.530  -5.130   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.054  -3.665   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.211  -1.671   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.389  -1.671   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.033  -3.267   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.432  -1.779   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -7.122  -4.356   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0      -1.441  -6.219   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      -1.043  -7.706   0.000  0.00  0.00           H+0
CONECT    1    2    5    6    7                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    1    4                                                       
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-stachydrine	HMDB
(2R)-4-Hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylic acid	HMDB

Chemical Formula

C₇H₁₃NO₃

Average Molecular Weight

159.183

Monoisotopic Molecular Weight

159.089543287

IUPAC Name

(2R)-4-hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

Traditional Name

(2R)-4-hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1C[C@H](C([O-])=O)[N+](C)(C)C1

InChI Identifier

InChI=1S/C7H13NO3/c1-8(2)4-5(9)3-6(8)7(10)11/h5-6,9H,3-4H2,1-2H3/t5?,6-/m1/s1

InChI Key

MUNWAHDYFVYIKH-PRJDIBJQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline 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

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
D-alpha-amino acid
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
N-alkylpyrrolidine
Tetraalkylammonium salt
Pyrrolidine
Quaternary ammonium salt
1,2-aminoalcohol
Carboxylic acid salt
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organic oxygen compound
Organic salt
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0029230)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	12.2 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-5	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.06	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.43 m³·mol⁻¹	ChemAxon
Polarizability	15.94 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	140.837	30932474
DeepCCS	[M-H]-	138.942	30932474
DeepCCS	[M-2H]-	172.49	30932474
DeepCCS	[M+Na]+	146.739	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.4	32859911
AllCCS	[M+NH4]+	135.5	32859911
AllCCS	[M+Na]+	136.6	32859911
AllCCS	[M-H]-	139.7	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	142.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxystachydrine	[H]OC1C[C@H](C([O-])=O)[N+](C)(C)C1	2005.0	Standard polar	33892256
4-Hydroxystachydrine	[H]OC1C[C@H](C([O-])=O)[N+](C)(C)C1	1091.9	Standard non polar	33892256
4-Hydroxystachydrine	[H]OC1C[C@H](C([O-])=O)[N+](C)(C)C1	1210.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxystachydrine,1TMS,isomer #1	C[N+]1(C)CC(O[Si](C)(C)C)C[C@@H]1C(=O)[O-]	1362.2	Semi standard non polar	33892256
4-Hydroxystachydrine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C[C@H](C(=O)[O-])[N+](C)(C)C1	1627.0	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 - 4-Hydroxystachydrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-9200000000-0e9aa3946ab45dd45de9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxystachydrine GC-MS (1 TMS) - 70eV, Positive	splash10-0629-6900000000-39b7181df315007ea028	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxystachydrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxystachydrine 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 - 4-Hydroxystachydrine 10V, Positive-QTOF	splash10-03dl-0900000000-80f7e3ac2a14fd2d2482	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 20V, Positive-QTOF	splash10-03dl-3900000000-7c6c1dea7205878a156c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 40V, Positive-QTOF	splash10-05ai-9000000000-9c319ded53898862d1ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 10V, Negative-QTOF	splash10-0a4i-0900000000-0aad6353c9033109cfee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 20V, Negative-QTOF	splash10-0a4i-0900000000-ba77d750e0e586b0e8dd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 40V, Negative-QTOF	splash10-0pi3-9000000000-6348b214e0971b1f33c2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 10V, Positive-QTOF	splash10-03di-0900000000-ebfb47d40d34e9a01631	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 20V, Positive-QTOF	splash10-03dl-4900000000-5bd837244c3b53e24af8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 40V, Positive-QTOF	splash10-052k-9100000000-87d96899ab48d138172b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 10V, Negative-QTOF	splash10-0a4i-0900000000-bae995f985c28e19f14c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 20V, Negative-QTOF	splash10-0a4i-0900000000-071902c1d72edaf79bd1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxystachydrine 40V, Negative-QTOF	splash10-0006-9000000000-fe61bd09f478156455f7	2021-09-23	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

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

FDB111659

KNApSAcK ID

Not Available

Chemspider ID

333078

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

375481

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 4-Hydroxystachydrine (HMDB0029230)

MOL for HMDB0029230 (4-Hydroxystachydrine)

3D MOL for HMDB0029230 (4-Hydroxystachydrine)

3D SDF for HMDB0029230 (4-Hydroxystachydrine)

3D-SDF for HMDB0029230 (4-Hydroxystachydrine)

PDB for HMDB0029230 (4-Hydroxystachydrine)

3D PDB for HMDB0029230 (4-Hydroxystachydrine)

SMILES for HMDB0029230 (4-Hydroxystachydrine)

INCHI for HMDB0029230 (4-Hydroxystachydrine)

Structure for HMDB0029230 (4-Hydroxystachydrine)

3D Structure for HMDB0029230 (4-Hydroxystachydrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra