4-Hydroxyproline
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Basic Info
Common Name | 4-Hydroxyproline(F05370) |
2D Structure | |
Description | 4-Hydroxyproline (or hydroxyproline or Hyp) is a major component of the protein collagen. Hydroxyproline is produced by hydroxylation of the amino acid proline and is, therefore, a post-translationally modified amino acid. Hydroxyproline and proline play key roles for collagen stability. In particular, they permit the sharp twisting of the collagen helix. Hydroxyproline is found in few proteins other than collagen. The only other mammalian protein which includes hydroxyproline is elastin. For this reason, hydroxyproline content has been used as an indicator to determine collagen and/or gelatin amount in tissue or biological samples. Increased serum and urine levels of hydroxyproline have been found in Paget's disease Hydroxyproline (Hyp) content in biological fluids is used as a parameter of collagen catabolism, especially bone resorption or tissue degradation. Bedridden and elderly individuals show significantly elevated serum levels of hydroxyproline in comparison to normal, active individuals Elevated levels of urinary hydroxyproline are also indicative of muscle damage Increased reactive oxygen species (ROS) are also known to accelerate collagen degradation. Hydroxyproline levels increase in cases of depression and stress (A3486, A3487, A3488, A3489). |
FRCD ID | F05370 |
CAS Number | 51-35-4 |
PubChem CID | 5810 |
Formula | C5H9NO3 |
IUPAC Name | (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid |
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 |
Canonical SMILES | C1C(CNC1C(=O)O)O |
Isomeric SMILES | C1[C@H](CN[C@@H]1C(=O)O)O |
Wikipedia | 4-Hydroxyproline |
Synonyms | trans-4-Hydroxy-L-proline 51-35-4 hydroxyproline L-Hydroxyproline (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid L-4-hydroxyproline trans-4-Hydroxyproline hydroxy-L-proline 4-Hydroxy-L-proline H-Hyp-OH |
Classifies | Animal Toxin |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic acids and derivatives |
Class | Carboxylic acids and derivatives |
Subclass | Amino acids, peptides, and analogues |
Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
Direct Parent | Proline and derivatives |
Alternative Parents | |
Molecular Framework | Aliphatic heteromonocyclic compounds |
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 |
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. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 131.131 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 4 |
Rotatable Bond Count | 1 |
Complexity | 125 |
Monoisotopic Mass | 131.058 |
Exact Mass | 131.058 |
XLogP | -3.3 |
Formal Charge | 0 |
Heavy Atom Count | 9 |
Defined Atom Stereocenter Count | 2 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.6522 |
Human Intestinal Absorption | HIA+ | 0.9652 |
Caco-2 Permeability | Caco2- | 0.7144 |
P-glycoprotein Substrate | Non-substrate | 0.5460 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9789 |
Non-inhibitor | 0.9870 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8560 |
Distribution | ||
Subcellular localization | Mitochondria | 0.5864 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8242 |
CYP450 2D6 Substrate | Non-substrate | 0.7501 |
CYP450 3A4 Substrate | Non-substrate | 0.6878 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9332 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9619 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9367 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9623 |
CYP450 3A4 Inhibitor | Non-inhibitor | 1.0000 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9913 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9682 |
Non-inhibitor | 0.9178 | |
AMES Toxicity | Non AMES toxic | 0.9149 |
Carcinogens | Non-carcinogens | 0.9640 |
Fish Toxicity | Low FHMT | 0.9000 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.9720 |
Honey Bee Toxicity | Low HBT | 0.5710 |
Biodegradation | Ready biodegradable | 0.9178 |
Acute Oral Toxicity | III | 0.5577 |
Carcinogenicity (Three-class) | Non-required | 0.7268 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.3499 | LogS |
Caco-2 Permeability | 0.1806 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.1441 | LD50, mol/kg |
Fish Toxicity | 3.0514 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.9563 | pIGC50, ug/L |
Targets
- 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
- Thondorf I, Voigt V, Schafer S, Gebauer S, Zebisch K, Laug L, Brandsch M: Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1). Bioorg Med Chem. 2011 Nov 1;19(21):6409-18. doi: 10.1016/j.bmc.2011.08.058. Epub 2011 Sep 5. [21955456 ]