Compound: ectoine
SMILES: O=C(O)[C@H]1NC(=NCC1)C
InChIKey: WQXNXVUDBPYKBA-YFKPBYRVSA-N
Synonyms: ectoine, 96702-03-3, ectoin, (4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid, 7GXZ3858RY, (6S)-2-methyl-1,4,5,6-tetrahydropyrimidine-6-carboxylic acid, CHEBI:27592, DTXSID50869280, NSC-614616, 1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, (4S)-3,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, (4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylate, (6S)-2-methyl-1,4,5,6-tetrahydropyrimidin-3-ium-6-carboxylate, 4-Pyrimidinecarboxylic acid, 1,4,5,6-tetrahydro-2-methyl-, (+)-, RefChem:590567, DTXCID001765744, 2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid, NSC614616, L-Ectoine, (S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid, (S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid, MFCD03419286, 4-Pyrimidinecarboxylicacid, 3,4,5,6-tetrahydro-2-methyl-, (4S)-, (S)-2-Methyl- 1,4,5,6-tetrahydropyrimidine-4-carboxylic acid, (+)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, UNII-7GXZ3858RY, SMR000127407, Ectoine?, 4CS, Ectoine (Standard), Ectoine, osmoprotectant, ECTOINE [MI], ECTOINE [WHO-DD], SCHEMBL93532, US9138393, Ectoine, US9144538, Ectoine, MLS001332487, MLS001332488, SCHEMBL977252, orb1303265, CHEMBL1230264, BDBM181140, Ectoine, >=95.0% (HPLC), EX-A1678, 4-Pyrimidinecarboxylic acid, 1,4,5,6-tetrahydro-2-methyl-, (4S)-, MSK160506, s5591, AKOS006348056, AKOS027427031, CCG-266161, DS-3343, EBC-616375, FE44798, HY-107784R, NSC 614616, AC-33942, DA-63111, SY223897, HY-107784, CS-0030647, E1372, C06231, I11596, Ectoine, primary pharmaceutical reference standard, F541626, Q414414, (4S)-2-Methyl-1,4,5,6-tetrahydro-4-pyrimidinecarboxylic acid, (4s)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid, (S)-1,4,5,6-tetrahydro-2-methyl-4-pyrimi-dinecarboxylic acid, (s)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, (S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4 carboxylic acid, Ectoine (2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid)
Theoretical properties:
molecular_formula: C6H10N2O2
molecular_weight: 142.16 g/mol
exact_mass: 142.074227566 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 10
topological_polar_surface_area: 61.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Ectoine is a carboxamidine heterocycle obtained by formal condensation of (2S)-2,4-diaminobutanoic acid with acetic acid. It has a role as an osmolyte. It is a monocarboxylic acid, a carboxamidine and a member of 1,4,5,6-tetrahydropyrimidines. It is a conjugate acid of an ectoinate. It is a tautomer of an ectoine zwitterion.
chebi: A carboxamidine heterocycle obtained by formal condensation of (2<i>S</i>)-2,4-diaminobutanoic acid with acetic acid.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Ectoine (3,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a compatible solute which serves as a protective substance by acting as an osmolyte and thus helps organisms survive extreme osmotic stress. Furthermore it was shown to protect DNA against ionizing and ultraviolet radiation serving as a radical scavenger. Ectoine is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism Ectothiorhodospira halochloris, but has since been found in a wide range of Gram-negative and Gram-positive bacteria. Other species of bacteria in which ectoine was found include:

Brevibacterium linens
Halomonas elongata
Marinococcus halophilus
Pseudomonas stutzeri
Halomonas titanicae
Halorhodospira halophila
Halomonas ventosae