MiMeDB: Showing metabocard for trans-3-hydroxy-L-proline (MMDBc0054679)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:23:57 UTC

Update Date

2022-08-12 20:09:03 UTC

Metabolite ID

MMDBc0054679

Metabolite Identification

Common Name

trans-3-hydroxy-L-proline

Description

Trans-3-hydroxy-l-proline is a substrate for: Trans-L-3-hydroxyproline dehydratase.

Structure

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

Synonyms

Value	Source
(2S,3S)-3-Hydroxypyrrolidine-2-carboxylic acid	ChEBI
3-trans-Hydroxy-L-proline	ChEBI
L-Threo-3-hydroxyproline	ChEBI
trans-L-3-Hydroxyproline	ChEBI
(2S,3S)-3-Hydroxypyrrolidine-2-carboxylate	Generator

Molecular Formula

C₅H₉NO₃

Average Mass

131.1299

Monoisotopic Mass

131.058243159

IUPAC Name

(2S,3S)-3-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

trans-3-hydroxy-L-proline

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)CCN[C@]1([H])C(O)=O

InChI Identifier

InChI=1S/C5H9NO3/c7-3-1-2-6-4(3)5(8)9/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1

InChI Key

BJBUEDPLEOHJGE-IMJSIDKUSA-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
L-alpha-amino acid
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Pyrrolidine
Amino acid
Secondary alcohol
Carboxylic acid
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

3-hydroxy-L-proline (CHEBI:16889 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	431 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-3.7	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	1.61	ChemAxon
pKa (Strongest Basic)	10.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	29.38 m³·mol⁻¹	ChemAxon
Polarizability	12.33 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4i-1900000000-43167f7b02d5c91f7431	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-001i-2690000000-31769ffb5511f9fd00bf	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-1900000000-43167f7b02d5c91f7431	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-2690000000-31769ffb5511f9fd00bf	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9000000000-dc85246c192fc6318aa1	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-4910000000-4fa1d4ed0b9aee3e1fd0	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-2900000000-128ccf9715c5890c5404	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03xr-9600000000-8c3c68532a2b86bfd028	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr6-9000000000-d018e434f138775d4120	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-7900000000-3230ec745853fb03ffc2	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02u9-9300000000-8240d8b2c6fddad07085	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0673-9000000000-a3fea27c28e95706d0ec	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9400000000-f8803de3984022a6de11	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-7199742da3eaa66ad564	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-f8bbde6aa62a6d9afa3b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-df968a68e6f2ab76adc2	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9200000000-c73aa9b436f74ef75e9c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-08bc65f1f17e8bcb3d04	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0196275	Trans-L-3-hydroxyproline dehydratase	Enzyme	Q96EM0	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012887	trans-3-hydroxy-L-proline	1-Pyrroline-2-carboxylic acid	Trans-3-hydroxy-L-proline dehydratase	Hydration/dehydration of C-O bond	RHEA	34755880
MMDBr0016349	trans-3-hydroxy-L-proline	cis-3-hydroxy-D-proline	3-hydroxyproline 2-epimerase	Epimerization	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	13	Human ; Pig
Bacteria/NULL	Proteobacteria	2	Human ; Pig
Bacteria	Firmicutes	3	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0059659

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

389475

KEGG Compound ID

C05147

BioCyc ID

CPD-664

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440575

PDB ID

HY3

ChEBI ID

16889

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]

Showing metabocard for trans-3-hydroxy-L-proline (MMDBc0054679)

MOL for #<Metabolite:0x00007f5a90106368>

3D MOL for #<Metabolite:0x00007f5a90106368>

3D SDF for #<Metabolite:0x00007f5a90106368>

3D-SDF for #<Metabolite:0x00007f5a90106368>

PDB for #<Metabolite:0x00007f5a90106368>

3D PDB for #<Metabolite:0x00007f5a90106368>

SMILES for #<Metabolite:0x00007f5a90106368>

INCHI for #<Metabolite:0x00007f5a90106368>

Structure for #<Metabolite:0x00007f5a90106368>

3D Structure for #<Metabolite:0x00007f5a90106368>