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Record Information

Version

2.0

Creation Date

2015-09-08 17:49:12 -0600

Update Date

2015-09-08 17:49:12 -0600

Secondary Accession Numbers

ECMDB24088

Identification

Name:

4-Hydroxy-L-proline

Description

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Value	Source
(2S)-4-Hydroxypyrrolidine-2-carboxylic acid	ChEBI
cis-4-Hydroxy-L-proline	ChEBI
Hydroxy-L-proline	ChEBI
L-Hydroxyproline	ChEBI
(2S)-4-Hydroxypyrrolidine-2-carboxylate	Generator
(4S)-4-Hydroxy-L-proline	HMDB
allo-4-Hydroxy-L-proline	HMDB
allo-4-Hydroxyproline	HMDB
allo-Hydroxy-L-proline	HMDB
cis-4-Hydroxyproline	HMDB, MeSH
L-4-allo-Hydroxy-proline	HMDB
L-4-Hydroxy-proline	HMDB
L-4-Hydroxyproline	HMDB
L-Allohydroxyproline	HMDB
4-Hydroxyproline	MeSH
Oxyproline	MeSH
cis 4 Hydroxyproline	MeSH
Hydroxyproline	MeSH
4 Hydroxyproline	MeSH

Chemical Formula:

C₅H₉NO₃

Weight:

Average: 131.1299
Monoisotopic: 131.058243159

InChI Key:

PMMYEEVYMWASQN-BKLSDQPFSA-N

InChI:

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

CAS number:

Not Available

IUPAC Name:

(2S)-4-hydroxypyrrolidine-2-carboxylic acid

Traditional IUPAC Name:

4 hydroxyproline

SMILES:

OC1CN[C@@H](C1)C(O)=O

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
Pyrrolidine
1,2-aminoalcohol
Amino acid
Secondary alcohol
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Amine
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:18240 )
L-proline derivative (CHEBI:18240 )
4-hydroxyproline (CHEBI:18240 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	492 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.7	ChemAxon
logS	0.57	ALOGPS
pKa (Strongest Acidic)	1.64	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	12.32 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000x-0940000000-a668e3cb89c27d5aaaec	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-07g3-9100000000-7e4ece693ce885f2589c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-5910000000-8b634c853b803e2ce4d3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-9000000000-268874d675b6738960f8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-cc0c0c49fda47ff3c20a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-1900000000-091663d1fbe737185a8a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9100000000-b2aeae336cfe73f5d96e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014r-9000000000-cd33ebf7746baae48364	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9000000000-f7d527bb54521981a624	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9000000000-1c34470907bfbc038d07	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-2b450c503f28b7e56789	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-3885e554a98e35271b27	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-59edfed4387af678c85b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-c0b2003453a19bfc37d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02t9-9400000000-1e365ce40f4342e10983	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-95dfbe4457c528ad98ed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-4328dec4e0cf083ba05d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03yi-8900000000-a8cabd8deaa24da3b219	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9000000000-1216ea21a7fab26c6cf7	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18240
HMDB ID	HMDB0006055
Pubchem Compound ID	69248
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	4-hydroxy-L-proline
BioCyc ID	Not Available

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

4-Hydroxy-L-proline (M2MDB006205)

Structure for #<Compound:0xaadf5188>