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Identification
NameHydroxyproline
Accession NumberDB08847
TypeSmall Molecule
GroupsApproved, Experimental
DescriptionHydroxyproline is a neutral heterocyclic protein amino acid. It is found in collagen and as such it is common in many gelatin products. Hydroxyproline is mostly used as a diagnostic marker of bone turnover and liver fibrosis. Therapeutically, hydroxyproline is being studied as an an experimental medicine but is approved in France as a combination topical gel product called Cicactive for small, superficial wounds.
Structure
Thumb
Synonyms
L-Hydroxyproline
trans-4-Hydroxy-L-proline
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
O Hui Wrinkle Science Wrinkle Repaircream.5 1/100mLtopicalLG Household and Healthcare, Inc.2010-04-16Not applicableUs
Ohui Wrinkle Science Wrinkle Repair Eyecream.51 1/100mLtopicalLG Household and Healthcare, Inc.2010-04-16Not applicableUs
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Gongjinhyang Mi Luxury Foundation 2LG Household and Healthcare, Inc.
Isa Knox Ageless Serum Makeup Base 10LG Household and Healthcare, Inc.
Isa Knox Smart Bb SunLG Household and Healthcare, Inc.
Isaknox Ageless Serum Moist Pearl BaseLG Household and Healthcare, Inc.
Ohui The First Cell Revolution Age Control Sun BlockLG Household and Healthcare, Inc.
Ouhi Cell Power No 1 EssenceLG Household and Healthcare, Inc.
Sooryehan Onbit Essence Foundation 21LG Household and Healthcare, Inc.
SaltsNot Available
Categories
UNIIRMB44WO89X
CAS number51-35-4
WeightAverage: 131.1299
Monoisotopic: 131.058243159
Chemical FormulaC5H9NO3
InChI KeyInChIKey=PMMYEEVYMWASQN-ACHLYQRRNA-N
InChI
InChI=1/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4?/s2
IUPAC Name
(4S)-4-hydroxypyrrolidine-2-carboxylic acid
SMILES
O[C@@H]1CNC(C1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Pyrrolidine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in France as a combination product for the treatment of small, superficial wounds.
PharmacodynamicsHydroxyproline as well as proline and glycine are the major components of collagen. Collagen is on one of the main building blocks of connective tissue such as skin, bone, and cartilage. Thus when these tissues are damaged, hydroxyproline is necessary for repair of the damaged area.
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9652
Blood Brain Barrier+0.6522
Caco-2 permeable-0.7144
P-glycoprotein substrateNon-substrate0.546
P-glycoprotein inhibitor INon-inhibitor0.9789
P-glycoprotein inhibitor IINon-inhibitor0.987
Renal organic cation transporterNon-inhibitor0.856
CYP450 2C9 substrateNon-substrate0.8242
CYP450 2D6 substrateNon-substrate0.7501
CYP450 3A4 substrateNon-substrate0.6878
CYP450 1A2 substrateNon-inhibitor0.9332
CYP450 2C9 inhibitorNon-inhibitor0.9619
CYP450 2D6 inhibitorNon-inhibitor0.9367
CYP450 2C19 inhibitorNon-inhibitor0.9623
CYP450 3A4 inhibitorNon-inhibitor1.0
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9913
Ames testNon AMES toxic0.9149
CarcinogenicityNon-carcinogens0.964
BiodegradationReady biodegradable0.9178
Rat acute toxicity2.1441 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9682
hERG inhibition (predictor II)Non-inhibitor0.9178
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Creamtopical
Liquidtopical
Creamtopical.5 1/100mL
Creamtopical.51 1/100mL
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point274°CFrom The Merck Index monographs.
boiling pointDecomposesFrom MSDS.
water solubilitySoluble in water at 0, 25, 50, and 60 °CFrom The Merck Index monographs.
pKapK1′ 1.82 and pK2′ 9.65From The Merck Index monographs.
Predicted Properties
PropertyValueSource
Water Solubility492.0 mg/mLALOGPS
logP-3.3ALOGPS
logP-3.7ChemAxon
logS0.57ALOGPS
pKa (Strongest Acidic)1.64ChemAxon
pKa (Strongest Basic)10.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.38 m3·mol-1ChemAxon
Polarizability12.33 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Adams, Elijah; Goldstone, Alfred. Hydroxyproline metabolism. II. Enzymic preparation and properties of D1-pyrroline-3-hydroxy-5-carboxylic acid. Journal of Biological Chemistry (1960), 235 3492-8.

General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-proline transmembrane transporter activity
Specific Function:
Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
Gene Name:
SLC36A1
Uniprot ID:
Q7Z2H8
Molecular Weight:
53075.045 Da
References
  1. Metzner L, Kalbitz J, Brandsch M: Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1. J Pharmacol Exp Ther. 2004 Apr;309(1):28-35. Epub 2004 Jan 12. [PubMed:14718599 ]
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Drug created on March 01, 2013 18:29 / Updated on August 17, 2016 12:24