Showing Metabocard for trans-4-hydroxy-L-proline betaine (BASm0007407)
| Common Name | Trans-4-hydroxy-l-proline betaine |
|---|---|
| Description | Betonicine (4-hydroxy-L-prolinebetaine) and its cis isomer, turicine, are naturally occurring substituted pyrrolidines. It is not naturally produced by humans and can only be obtained through consumption of certain plant products. Betonicine was used as an analgesic 1000 years ago and is still available commercially from herbalists today. Betonicine has been isolated from Achillea millefolium L. (common yarrow) and probably from A. atrata L. (black yarrow); it is an alkaloid. Betonicine has been identified as a metabolically inert cell protectant that protects plants against extremes in osmolarity and growth temperatures. Betonicine is found in the fruit juices of yellow orange, blood orange, lemon, mandarin and bitter orange (PMID: 21838291 ) |
| Structure | |
| Molecular Formula | C7H13NO3 |
| Average Mass | 159.18300 |
| Monoisotopic Mass | 159.08954 |
| IUPAC Name | (2S,4R)-4-hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylate |
| Traditional Name | (-)-betonicine |
| CAS Registry Number | 515-25-3 |
| SMILES | C[N+]1(C)C[C@H](O)C[C@H]1C(=O)[O-] |
| InChI Identifier | InChI=1S/C7H13NO3/c1-8(2)4-5(9)3-6(8)7(10)11/h5-6,9H,3-4H2,1-2H3/t5-,6+/m1/s1 |
| InChI Key | MUNWAHDYFVYIKH-RITPCOANSA-N |
| CHEBI ID | CHEBI:85533 |
| HMDB ID | HMDB0029412 |
| State | Not Available |
| Water Solubility | 1.22e+01 g/l |
| logP | -1.54 |
| logS | -1.24 |
| pKa (Strongest Acidic) | 2.06 |
| pKa (Strongest Basic) | -3.56 |
| Hydrogen Acceptor Count | 3 |
| Hydrogen Donor Count | 1 |
| Polar Surface Area | 60.36 Ų |
| Rotatable Bond Count | 1 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 61.43 m³·mol⁻¹ |
| Polarizability | 15.90 |