Showing Compound Card for trans-Hydroxyproline (CDB006322)

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Record Information
Version1.0
Created at2020-09-11 15:49:02 UTC
Updated at2022-12-13 23:36:23 UTC
CannabisDB IDCDB006322
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-Hydroxyproline
Description4-Hydroxyproline, also known as Hyp or oxaceprol, 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. 4-Hydroxyproline is a drug which is used in france as a combination product for the treatment of small, superficial wounds. 4-Hydroxyproline is a very strong basic compound (based on its pKa). 4-Hydroxyproline exists in all living species, ranging from bacteria to humans. Within humans, 4-hydroxyproline participates in a number of enzymatic reactions. In particular, 4-hydroxyproline and succinic acid can be biosynthesized from L-proline and oxoglutaric acid through the action of the enzyme prolyl 4-hydroxylase. In addition, 4-hydroxyproline can be converted into pyrroline hydroxycarboxylic acid; which is catalyzed by the enzyme proline dehydrogenase 1, mitochondrial. In humans, 4-hydroxyproline is involved in the metabolic disorder called hyperornithinemia with gyrate atrophy (hoga). 4-Hydroxyproline is a potentially toxic compound. 4-Hydroxyproline, with regard to humans, has been found to be associated with several diseases such as periodontal probing depth, colorectal cancer, and alzheimer's disease; 4-hydroxyproline has also been linked to several inborn metabolic disorders including iminoglycinuria and hydroxyprolinemia. An optically active form of 4-hydroxyproline having L-trans-configuration.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylic acidChEBI
(2S,4R)-trans-4-HydroxyprolineChEBI
delta-HydroxyprolineChEBI
Hydroxy-L-prolineChEBI
HydroxyprolineChEBI
HypChEBI
HyproChEBI
L-4-HydroxyprolineChEBI
L-Threo-4-hydroxyprolineChEBI
trans-HydroxyprolineChEBI
trans-L-HydroxyprolineChEBI
L-HydroxyprolineKegg
trans-4-Hydroxy-L-prolineKegg
(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylateGenerator
Δ-hydroxyprolineGenerator
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acidHMDB
(4R)-4-Hydroxy-L-prolineHMDB
4-Hydroxy-2-pyrrolidinecarboxylic acidHMDB
4-Hydroxy-L-prolineHMDB
4-L-HydroxyprolineHMDB
HydroxiprolineHMDB
Hydroxy-prolineHMDB
LS-HydroxyprolineHMDB
OxaceprolHMDB
trans-4-HydroxyprolineHMDB
4 HydroxyprolineHMDB
OxyprolineHMDB
(-)-4-Hydroxy-2-pyrrolidinecarboxylic acidHMDB
(2S,4R)-(-)-4-HydroxyprolineHMDB
(2S,4R)-4-HydroxyprolineHMDB
(R)-4-Hydroxy-(S)-prolineHMDB
(R)-4-Hydroxy-L-prolineHMDB
(S)-HydroxyprolineHMDB
4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic acidHMDB
4(R)-HydroxyprolineHMDB
4-Hydroxy-(S)-prolineHMDB
4-trans-Hydroxy-L-prolineHMDB
L-HyproHMDB
L-trans-4-HydroxyprolineHMDB
NSC 46704HMDB
trans-L-4-HydroxyprolineHMDB
4-HydroxyprolineHMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
Traditional Namehypro
CAS Registry NumberNot Available
SMILES
O[C@H]1CN[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+/m1/s1
InChI KeyPMMYEEVYMWASQN-DMTCNVIQSA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.38 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00ku-9000000000-f5bd67093b2f30a6f62b2018-05-25View Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-000x-0950000000-5b1c397e26b28e872d20Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-000x-0950000000-c46b5bba0f41001e3c18Spectrum
GC-MStrans-Hydroxyproline, 3 TMS, GC-MS Spectrumsplash10-00di-9530000000-00db00b15ab5341d7d64Spectrum
GC-MStrans-Hydroxyproline, 2 TMS, GC-MS Spectrumsplash10-0a4i-1900000000-c0a869abe2f1e9f8c08eSpectrum
GC-MStrans-Hydroxyproline, 3 TMS, GC-MS Spectrumsplash10-001l-1960000000-abcd0377696d2b52d815Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-001i-0590000000-75e03328fb2d44469057Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-000x-0950000000-c46b5bba0f41001e3c18Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-00di-9530000000-00db00b15ab5341d7d64Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-0a4i-1900000000-c0a869abe2f1e9f8c08eSpectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-001l-1960000000-abcd0377696d2b52d815Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-000x-0940000000-97328204c6b60a244616Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-000x-0940000000-468aeb79950a9e6dadc6Spectrum
GC-MStrans-Hydroxyproline, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-40c0bfa9451caacaf422Spectrum
Predicted GC-MStrans-Hydroxyproline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6r-9100000000-af92b4a861832ca4ec13Spectrum
Predicted GC-MStrans-Hydroxyproline, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02mu-9670000000-81c8390bdfa262fa9b2fSpectrum
Predicted GC-MStrans-Hydroxyproline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Hydroxyproline, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0019-9700000000-ea3ed008938a57d1263c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014r-9000000000-0b76109525f362b600a02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-477e41e40831316e68ac2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0019-9300000000-7228a10f32d447b58ee02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-11800ca52c6e911f83132012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-11800ca52c6e911f83132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-1900000000-b6bba00a324b6eab209f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-1900000000-ba9df49a4d967cf8851d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-9000000000-6d125b0bb59101e9ce532017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0019-9300000000-7228a10f32d447b58ee02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0019-9600000000-5bcced64c9dfeb96876f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0019-9600000000-b575fa8df5e2d8bb3a992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-c036fd15ccf6ed0c554e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-8746de5249187bab94dc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-3f70e8e1eef8568e87ef2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-cd32fa744ef013f5ca482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-3ea6a86203c48888d5282021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-02tc-9000000000-95aa07d1970d7f83f3472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014r-9000000000-95b2178b5433b4b2db502021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-a10576d40ff1d7fc707a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-9400000000-8b66308781907cdf63042016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-7f9d42864b2decdbdd1d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-bfc9154f784caa2e61a72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ar-9800000000-750b3fd4f0e1dcb8ef4c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9000000000-efe39f47f6ee937ded3d2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00216 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00344 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00445 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.00327 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00304 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00380 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000725
DrugBank IDDB08847
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013511
KNApSAcK IDC00001370
Chemspider ID5605
KEGG Compound IDC01157
BioCyc ID4-HYDROXY-L-PROLINE
BiGG ID36935
Wikipedia LinkHydroxyproline
METLIN ID257
PubChem Compound5810
PDB IDNot Available
ChEBI ID18095
References
General ReferencesNot Available