Hydroxyproline

Identification

Name
Hydroxyproline
Accession Number
DB08847
Type
Small Molecule
Groups
Approved, Experimental
Description

Hydroxyproline 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
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
O Hui Wrinkle Science Wrinkle RepairCream.5 1/100mLTopicalLg Household & Health Care Ltd.2010-04-16Not applicableUs
OHUI Wrinkle Science wrinkle repair eyeCream.51 1/100mLTopicalLg Household & Health Care Ltd.2010-04-16Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Gongjinhyang Mi Luxury Foundation 2Hydroxyproline (.53 mL/100mL) + Octinoxate (1 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-03-30Not applicableUs
Isa Knox Ageless Serum Makeup Base 10Hydroxyproline (.53 mL/100mL) + Aluminum hydroxide (.18 mL/100mL) + Dimethicone (.08 mL/100mL) + Octinoxate (3 mL/100mL) + Stearic acid (.18 mL/100mL) + Titanium dioxide (3.38 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-07-04Not applicableUs
Isa Knox Smart Bb SunHydroxyproline (.5 mL/100mL) + Atractylodes japonica root oil (.05 mL/100mL) + Octinoxate (7 mL/100mL) + Titanium dioxide (6.72 mL/100mL) + Zinc oxide (2.88 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-04-12Not applicableUs
Isaknox Ageless Serum Moist Pearl BaseHydroxyproline (.53 mL/100mL) + Aluminum hydroxide (.18 mL/100mL) + Dimethicone (.08 mL/100mL) + Octinoxate (3 mL/100mL) + Stearic acid (.18 mL/100mL) + Titanium dioxide (3.38 mL/100mL)LiquidTopicalLg Household & Health Care Ltd.2010-08-31Not applicableUs
Ohui The First Cell Revolution Age Control Sun BlockHydroxyproline (.5 g/100g) + Diethylamino hydroxybenzoyl hexyl benzoate (.5 g/100g) + Ensulizole (3.9 g/100g) + Octinoxate (7 g/100g) + Octisalate (4.8 g/100g) + Titanium dioxide (6 g/100g)CreamTopicalLg Household & Health Care Ltd.2011-04-06Not applicableUs
Ouhi Cell Power No 1 EssenceHydroxyproline (.5 mL/100mL) + Nicotinamide (2 mL/100mL)LiquidTopicalLg Household & Health Care Ltd.2010-12-03Not applicableUs
Sooryehan Onbit Essence Foundation 21Hydroxyproline (.5 mL/100mL) + Aluminum hydroxide (.1 mL/100mL) + Octinoxate (3 mL/100mL) + Stearic acid (.1 mL/100mL) + Titanium dioxide (.8 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-08-25Not applicableUs
Categories
UNII
RMB44WO89X
CAS number
51-35-4
Weight
Average: 131.1299
Monoisotopic: 131.058243159
Chemical Formula
C5H9NO3
InChI Key
PMMYEEVYMWASQN-DMTCNVIQSA-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+/m1/s1
IUPAC Name
(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
SMILES

Pharmacology

Indication

Used in France as a combination product for the treatment of small, superficial wounds.

Structured Indications
Not Available
Pharmacodynamics

Hydroxyproline 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 action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00725
KEGG Compound
C01157
PubChem Compound
5810
PubChem Substance
175427120
ChemSpider
5605
BindingDB
50357233
ChEBI
18095
ChEMBL
CHEMBL352418
HET
HYP
Wikipedia
Hydroxyproline
PDB Entries
1ag7 / 1as5 / 1av3 / 1bdk / 1bkv / 1cag / 1cgd / 1d7t / 1dfy / 1dfz
show 174 more
MSDS
Download (72.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedTreatmentHyperoxaluria1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamTopical
LiquidTopical
CreamTopical.5 1/100mL
CreamTopical.51 1/100mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)274°CFrom The Merck Index monographs.
boiling point (°C)DecomposesFrom 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
Polarizability12.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000x-0950000000-5b1c397e26b28e872d20
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000x-0950000000-c46b5bba0f41001e3c18
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-9530000000-00db00b15ab5341d7d64
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0a4i-1900000000-c0a869abe2f1e9f8c08e
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-001l-1960000000-abcd0377696d2b52d815
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-0590000000-75e03328fb2d44469057
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000x-0950000000-c46b5bba0f41001e3c18
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9530000000-00db00b15ab5341d7d64
GC-MS Spectrum - GC-MSGC-MSsplash10-0a4i-1900000000-c0a869abe2f1e9f8c08e
GC-MS Spectrum - GC-MSGC-MSsplash10-001l-1960000000-abcd0377696d2b52d815
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000x-0940000000-97328204c6b60a244616
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000x-0940000000-468aeb79950a9e6dadc6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0900000000-40c0bfa9451caacaf422
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0019-9700000000-ea3ed008938a57d1263c
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-014r-9000000000-0b76109525f362b600a0
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014l-9000000000-477e41e40831316e68ac
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0019-9300000000-7228a10f32d447b58ee0
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0900000000-11800ca52c6e911f8313
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0900000000-11800ca52c6e911f8313
MS/MS Spectrum - , negativeLC-MS/MSsplash10-001i-1900000000-b6bba00a324b6eab209f
MS/MS Spectrum - , negativeLC-MS/MSsplash10-001i-1900000000-ba9df49a4d967cf8851d
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-9000000000-6d125b0bb59101e9ce53
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0019-9300000000-7228a10f32d447b58ee0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0019-9600000000-5bcced64c9dfeb96876f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0019-9600000000-b575fa8df5e2d8bb3a99
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as proline and derivatives. These 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
L-alpha-amino acids / Pyrrolidine carboxylic acids / Secondary alcohols / Amino acids / 1,2-aminoalcohols / Monocarboxylic acids and derivatives / Dialkylamines / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 3 more
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
show 16 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
4-hydroxyproline (CHEBI:18095) / Other amino acids (C01157)

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 recog...
Gene Name
SLC36A1
Uniprot ID
Q7Z2H8
Uniprot Name
Proton-coupled amino acid transporter 1
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]

Drug created on March 01, 2013 18:29 / Updated on November 09, 2017 04:41