1.0 2015-02-26 20:21:15 UTC 2025-11-19 03:00:11 UTC FDB030011 cis 4-Hydroxyproline Cis 4-hydroxyproline, also known as L-allo-hydroxyproline or (2s,4s)-4-hydroxy-2-pyrrolidinecarboxylic acid, belongs to proline and derivatives class of compounds. Those 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. Cis 4-hydroxyproline is soluble (in water) and a moderately acidic compound (based on its pKa). Cis 4-hydroxyproline can be found in a number of food items such as green bell pepper, wheat, nanking cherry, and oat, which makes cis 4-hydroxyproline a potential biomarker for the consumption of these food products. C5H9NO3 131.1299 131.058243159 (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid L-hydroxyproline 618-27-9 O[C@@H]1CN[C@@H](C1)C(O)=O InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1 PMMYEEVYMWASQN-IMJSIDKUSA-N 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. Proline and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic heteromonocyclic compounds 1,2-aminoalcohols Amino acids Azacyclic compounds Carbonyl compounds Carboxylic acids Dialkylamines Hydrocarbon derivatives L-alpha-amino acids Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Pyrrolidine carboxylic acids Secondary alcohols 1,2-aminoalcohol Alcohol Aliphatic heteromonocyclic compound Alpha-amino acid Amine Amino acid Azacycle Carbonyl group Carboxylic acid Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Proline or derivatives Pyrrolidine Pyrrolidine carboxylic acid Pyrrolidine carboxylic acid or derivatives Secondary alcohol Secondary aliphatic amine Secondary amine 4-hydroxyproline non-proteinogenic L-alpha-amino acid logp -3.31 ALOGPS logs 0.57 ALOGPS solubility 4.92e+02 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 1.64 ChemAxon pka_strongest_basic 10.62 ChemAxon iupac (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid ChemAxon average_mass 131.1299 ChemAxon mono_mass 131.058243159 ChemAxon smiles O[C@@H]1CN[C@@H](C1)C(O)=O ChemAxon formula C5H9NO3 ChemAxon 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-/m0/s1 ChemAxon inchikey PMMYEEVYMWASQN-IMJSIDKUSA-N ChemAxon polar_surface_area 69.56 ChemAxon refractivity 29.38 ChemAxon polarizability 12.22 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 171953 Specdb::MsMs 1279069 Specdb::MsMs 1279070 Specdb::MsMs 1279071 Specdb::MsMs 1393963 Specdb::MsMs 1393964 Specdb::MsMs 1393965 Specdb::MsMs 2226374 Specdb::MsMs 2228701 Specdb::MsMs 2230724 Specdb::MsMs 2384249 Specdb::MsMs 2384250 Specdb::MsMs 2384251 Specdb::MsMs 2581701 Specdb::MsMs 2581702 Specdb::MsMs 2581703 Specdb::NmrOneD 72232 Specdb::NmrOneD 72233 Specdb::NmrOneD 72234 Specdb::NmrOneD 72235 Specdb::NmrOneD 72236 Specdb::NmrOneD 72237 Specdb::NmrOneD 72238 Specdb::NmrOneD 72239 Specdb::NmrOneD 72240 Specdb::NmrOneD 72241 Specdb::NmrOneD 72242 Specdb::NmrOneD 72243 Specdb::NmrOneD 72244 Specdb::NmrOneD 72245 Specdb::NmrOneD 72246 Specdb::NmrOneD 72247 Specdb::NmrOneD 72248 Specdb::NmrOneD 72249 Specdb::NmrOneD 72250 Specdb::NmrOneD 72251 Barley Type 1 specific Hordeum vulgare 4513 4.348222 4.35 4.34644382 mg/100 g Broccoli Type 1 specific Brassica oleracea var. italica 36774 0.3 0.3 0.3 mg/100 g Carrot Type 1 specific Daucus carota ssp. sativus 79200 0.04 0.04 0.04 mg/100 g Cucumber Type 1 specific Cucumis sativus 3659 0.02 0.02 0.02 mg/100 g Dill Type 1 specific Anethum graveolens 40922 0.19 0.19 0.19 mg/100 g Eggplant Type 1 specific Solanum melongena 4111 0.16 0.16 0.16 mg/100 g Garden onion Type 1 specific Allium cepa 4679 0.08 0.08 0.08 mg/100 g Green bean Type 1 specific Phaseolus vulgaris 3885 0.39 0.39 0.39 mg/100 g Green bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Green zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.09 0.09 0.09 mg/100 g Japanese pumpkin Type 1 specific Cucurbita maxima 3661 0.07 0.07 0.07 mg/100 g Nanking cherry Type 1 specific Prunus tomentosa 105667 2.0 2.0 2.0 mg/100 g Oat Type 1 specific Avena sativa 4498 6.36 6.36 6.36 mg/100 g Orange bell pepper Type 1 specific Capsicum annuum 4072 0.09 0.09 0.09 mg/100 g Parsnip Type 1 specific Pastinaca sativa 4041 0.168849 0.17 0.167698648 mg/100 g Potato Type 1 specific Solanum tuberosum 4113 0.08 0.08 0.08 mg/100 g Red beetroot Type 1 specific Beta vulgaris var. rubra 0.11 0.11 0.11 mg/100 g Red bell pepper Type 1 specific Capsicum annuum 4072 0.049478 0.05 0.0489552 mg/100 g Red raspberry Type 1 specific Rubus idaeus 32247 1.038281 1.038280615 1.038280615 mg/100 g Romaine lettuce Type 1 specific Lactuca sativa L. var. longifolia 0.1 0.1 0.1 mg/100 g Rye Type 1 specific Secale cereale 4550 5.655 7.99 3.32 mg/100 g Saskatoon berry Type 1 specific Amelanchier alnifolia 32219 0.4 0.4 0.4 mg/100 g Spinach Type 1 specific Spinacia oleracea 3562 0.13 0.13 0.13 mg/100 g Sunburst squash (pattypan squash) Type 1 specific Cucurbita pepo var. clypeata 0.08 0.08 0.08 mg/100 g Swiss chard Type 1 specific Beta vulgaris ssp. cicla 1527200 0.96076 0.961519053 0.96 mg/100 g Turnip Type 1 specific Brassica rapa var. rapa 51350 0.04 0.04 0.04 mg/100 g Wheat Type 1 specific Triticum 4564 5.01097 5.011939904 5.01 mg/100 g White cabbage Type 1 specific Brassica oleracea L. var. capitata L. f. alba DC. 0.08 0.08 0.08 mg/100 g Yellow bell pepper Type 1 specific Capsicum annuum 4072 0.07 0.07 0.07 mg/100 g Yellow wax bean Type 1 specific Phaseolus vulgaris 3885 0.8 0.8 0.8 mg/100 g Yellow zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.36 0.61 0.11 mg/100 g