Rosmarinate
PubChem CID: 5315615
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| Compound Synonyms | Rosmarinate, 537-15-5, Rosmarinic acid (racemate), CHEMBL66966, CHEBI:17226, NSC687846, Benzenepropanoic acid,a-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-, 3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid, Rosemarinic Acid, SR-01000597653, Rosmarinsaure, rosmarinate acid, 3-(3,4-dihydroxyphenyl)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid, SCHEMBL19348, BSPBio_003595, MLS001097740, SPECTRUM1502094, cid_5315615, GTPL13092, HMS1921J08, HY-N2336, BDBM50059986, AKOS024283449, CCG-214251, CS-6460, NSC-687846, 2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-(3,4-dihydroxyphenyl)propano ic acid, 3-(3,4-dihydroxyphenyl)-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid, alpha-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoic acid, NCGC00094959-01, NCGC00094959-02, NCGC00094959-03, NCGC00094959-04, SMR000578091, TS-10190, Q7762, EN300-718656, SR-01000597653-1, SR-01000597653-4, BRD-A03397678-001-06-2, 3-(3,4-dihydroxyphenyl)-2-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)propanoic acid, 3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propanoic acid, (R)-.alpha.-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2E-propenyl]oxy]-3,4-dihydroxybenzenepropanoic acid, 179462-74-9 |
|---|---|
| Topological Polar Surface Area | 145.0 |
| Hydrogen Bond Donor Count | 5.0 |
| Heavy Atom Count | 26.0 |
| Description | Isolated from rosemary, mint, sage, thyme, lemon balm and other plants Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. It is a red-orange powder that is slightly soluble in water, but well soluble is most organic solvents. Rosmarinic acid is one of the polyphenolic substances contained in culinary herbs such as perilla (Perilla frutescens L.), rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). These herbs are commonly grown in the garden as kitchen herbs, and while used to add flavor in cooking, are also known to have several potent physiological effects. (PMID: 12482446, 15120569), Rosmarinic acid, C18H16O8, is a natural polyphenol antioxidant carboxylic acid found in many Lamiaceae herbs used commonly as culinary herbs such as lemon balm, rosemary, oregano, sage, thyme and peppermint. Chemically, rosmarinic acid is an ester of caffeic acid with 3,4-dihydroxyphenyl lactic acid. It is a red-orange powder that is slightly soluble in water, but well soluble in most organic solvents. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 519.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | P46063, Q99714, B2RXH2, Q9NUW8, P10636, P25779, Q962Y6, Q9XUB2, Q9F4F7, O97447, P00811, P15428, P97697, P10253, P06746, G5EF15, O75164, O15648, Q92830, Q96KQ7, Q9UIF8, Q13951, O95149, P83916, Q9UNA4, P39748, Q9Y253, Q9UBT6, P07378, Q9H0H5, O94925, Q57TT1, Q4GZG4, Q9NR56, P27695, O00167, n.a. |
| Iupac Name | 3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid |
| Prediction Hob | 0.0 |
| Class | Cinnamic acids and derivatives |
| Target Id | NPT47, NPT149, NPT48, NPT50, NPT51, NPT151, NPT60, NPT59 |
| Xlogp | 2.4 |
| Superclass | Phenylpropanoids and polyketides |
| Subclass | Hydroxycinnamic acids and derivatives |
| Molecular Formula | C18H16O8 |
| Prediction Swissadme | 0.0 |
| Inchi Key | DOUMFZQKYFQNTF-ZZXKWVIFSA-N |
| Fcsp3 | 0.1111111111111111 |
| Logs | -2.432 |
| Rotatable Bond Count | 7.0 |
| State | Solid |
| Logd | 1.65 |
| Synonyms | (2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactate, (2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid, Labiatenic acid, Rosemarinic acid, Rosemary acid, Rosmarinate, Rosmarinic acid |
| Substituent Name | Cinnamic acid ester, Coumaric acid or derivatives, 3-phenylpropanoic-acid, Phenylpropene, Styrene, 1,2-diphenol, Phenol, Fatty acid ester, Fatty acyl, Benzenoid, Dicarboxylic acid or derivatives, Monocyclic benzene moiety, Alpha,beta-unsaturated carboxylic ester, Enoate ester, Carboxylic acid ester, Ether, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aromatic homomonocyclic compound |
| Compound Name | Rosmarinate |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 360.085 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 360.085 |
| Hydrogen Bond Acceptor Count | 8.0 |
| Molecular Weight | 360.3 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 1.0 |
| Esol | -3.4403100615384616 |
| Inchi | InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+ |
| Smiles | C1=CC(=C(C=C1CC(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O |
| Nring | 2.0 |
| Defined Bond Stereocenter Count | 1.0 |
- 1. Outgoing r'ship
FOUND_INto/from Anethum Graveolens (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Artemisia Dracunculus (Plant) Rel Props:Source_db:fooddb_chem_all - 3. Outgoing r'ship
FOUND_INto/from Borago Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 4. Outgoing r'ship
FOUND_INto/from Foeniculum Vulgare (Plant) Rel Props:Source_db:npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Hyssopus Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 6. Outgoing r'ship
FOUND_INto/from Isodon Rubescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 7. Outgoing r'ship
FOUND_INto/from Lycopus Lucidus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 8. Outgoing r'ship
FOUND_INto/from Melissa Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 9. Outgoing r'ship
FOUND_INto/from Mentha Aquatica (Plant) Rel Props:Source_db:fooddb_chem_all - 10. Outgoing r'ship
FOUND_INto/from Mentha Arvensis (Plant) Rel Props:Source_db:fooddb_chem_all - 11. Outgoing r'ship
FOUND_INto/from Mentha Longifolia (Plant) Rel Props:Source_db:fooddb_chem_all - 12. Outgoing r'ship
FOUND_INto/from Mentha Spicata (Plant) Rel Props:Source_db:fooddb_chem_all - 13. Outgoing r'ship
FOUND_INto/from Momordica Charantia (Plant) Rel Props:Source_db:fooddb_chem_all - 14. Outgoing r'ship
FOUND_INto/from Ocimum Basilicum (Plant) Rel Props:Source_db:fooddb_chem_all - 15. Outgoing r'ship
FOUND_INto/from Origanum Majorana (Plant) Rel Props:Source_db:fooddb_chem_all - 16. Outgoing r'ship
FOUND_INto/from Origanum Vulgare (Plant) Rel Props:Source_db:fooddb_chem_all - 17. Outgoing r'ship
FOUND_INto/from Perilla Frutescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 18. Outgoing r'ship
FOUND_INto/from Petroselinum Crispum (Plant) Rel Props:Source_db:fooddb_chem_all - 19. Outgoing r'ship
FOUND_INto/from Prunus Mume (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 20. Outgoing r'ship
FOUND_INto/from Rosmarinus Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 21. Outgoing r'ship
FOUND_INto/from Salvia Miltiorrhiza (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 22. Outgoing r'ship
FOUND_INto/from Salvia Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 23. Outgoing r'ship
FOUND_INto/from Satureja Hortensis (Plant) Rel Props:Source_db:fooddb_chem_all - 24. Outgoing r'ship
FOUND_INto/from Satureja Montana (Plant) Rel Props:Source_db:fooddb_chem_all - 25. Outgoing r'ship
FOUND_INto/from Thymus Vulgaris (Plant) Rel Props:Source_db:fooddb_chem_all - 26. Outgoing r'ship
FOUND_INto/from Vaccinium Corymbosum (Plant) Rel Props:Source_db:fooddb_chem_all