ChemFOnt: Showing chemical card for cis-4-Hydroxyproline (CFc000220515)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:39 UTC

Chemfont ID

CFc000220515

Molecule Identification

Common Name

cis-4-Hydroxyproline

Definition

cis-4-Hydroxyproline is classified as a proline derivative. It is considered to be a soluble (in water), acidic compound. cis-4-Hydroxyproline can be found in numerous foods such as dills, green zucchinis, saskatoon berries, and Japanese pumpkins.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylic acid	ChEBI
4-cis-L-Hydroxyproline	ChEBI
Allo-4-hydroxy-L-proline	ChEBI
L-Allo-hydroxyproline	ChEBI
L-cis-4-Hydroxyproline	ChEBI
L-Allohydroxyproline	Kegg
(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylate	Generator
cis-4-Hydroxy-L-proline	HMDB
cis-Hydroxyproline	HMDB
(4S)-4-Hydroxy-L-proline	HMDB
(2S,4S)-4-Hydroxyproline	HMDB
(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid	HMDB
(S)-allo-Hydroxyproline	HMDB
4(S)-Hydroxy-2(S)-pyrrolidinecarboxylic acid	HMDB
4-cis-Hydroxy-L-proline	HMDB
4-allo-Hydroxyproline	HMDB
L-allo-4-Hydroxyproline	HMDB
allo-4-Hydroxyproline	HMDB
allo-Hydroxy-L-proline	HMDB
allo-L-Hydroxyproline	HMDB
H-cis-Hyp-OH	HMDB
NSC 206274	HMDB
cis-4-Hydroxyproline	HMDB, MeSH
Hydroxyproline	MeSH, HMDB
4 Hydroxyproline	MeSH, HMDB
4-Hydroxyproline	MeSH, HMDB
Oxyproline	MeSH, HMDB
cis 4 Hydroxyproline	MeSH, HMDB

Chemical Formula

C₅H₉NO₃

Average Molecular Weight

131.1299

Monoisotopic Molecular Weight

131.058243159

IUPAC Name

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

Traditional Name

L-hydroxyproline

CAS Registry Number

618-27-9

SMILES

[H][C@@]1(O)CN[C@@]([H])(C1)C(O)=O

InChI Identifier

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

InChI Key

PMMYEEVYMWASQN-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
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:28397 )
4-hydroxyproline (CHEBI:28397 )

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0240251)

Broccoli (FooDB: FOOD00034)
White cabbage (FooDB: FOOD00887)

Leaf vegetable

Tuber

Potato (FooDB: FOOD00175)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Oat (FooDB: FOOD00022)
Rye (FooDB: FOOD00169)
Wheat (FooDB: FOOD00561)

Gourd

Cucumber (FooDB: FOOD00065)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Herb and spice

Herb

Dill (FooDB: FOOD00013)
Turnip (FooDB: FOOD00036)

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Process

Not Available

Role

Biological role

Waste product (PMID: 35448883)

Physical Properties

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	12.22 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

External Links

HMDB ID

HMDB0240251

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28397

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for cis-4-Hydroxyproline (CFc000220515)

MOL for CFc000220515 (cis-4-Hydroxyproline)

3D MOL for CFc000220515 (cis-4-Hydroxyproline)

3D SDF for CFc000220515 (cis-4-Hydroxyproline)

3D-SDF for CFc000220515 (cis-4-Hydroxyproline)

PDB for CFc000220515 (cis-4-Hydroxyproline)

3D PDB for CFc000220515 (cis-4-Hydroxyproline)

SMILES for CFc000220515 (cis-4-Hydroxyproline)

INCHI for CFc000220515 (cis-4-Hydroxyproline)

Structure for CFc000220515 (cis-4-Hydroxyproline)

3D Structure for CFc000220515 (cis-4-Hydroxyproline)