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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 00:44:12 UTC

Update Date

2021-10-13 04:42:02 UTC

HMDB ID

HMDB0003572

Secondary Accession Numbers

HMDB0002887
HMDB0124941
HMDB02887
HMDB03572

Metabolite Identification

Common Name

Rosmarinic acid

Description

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 ). BioTransformer predicts that rosmarinic acid is a product of methylrosmarinic acid metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in humans and human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309272007312D          

 26 27  0  0  0  0            999 V2000
10000.5946 9998.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8806 9999.0041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.1646 9998.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4502 9999.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7354 9998.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0205 9999.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5888 9996.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.1612 9997.3537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4502 9999.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8806 9999.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.594610000.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.164610000.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.026710001.0676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.454810000.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.7390 9999.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.024710000.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3102 9999.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3102 9999.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0246 9998.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.7390 9999.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5901 9999.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8758 9998.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8758 9997.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5901 9997.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3045 9997.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3045 9998.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
  1 18  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 21  1  0  0  0  0
 23  8  1  0  0  0  0
 24  7  1  0  0  0  0
  6 26  1  0  0  0  0
M  END

HMDB0003572
     RDKit          3D
Rosmarinic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.2063   -1.1387    2.5435 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5402   -0.5879    1.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970   -0.8514    1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7187   -0.2400    0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1457   -0.4290    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -1.2728    1.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2342   -1.4020    1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8837   -0.6947    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2454   -0.8172   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363    0.1448   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    0.8735   -1.5893 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    0.2936   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    0.3010    0.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422    0.5531    0.8962 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0052   -0.0385   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4530    0.1155   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798    1.2349   -1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3497    1.3330   -1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1772    0.3440   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5673    0.4560   -0.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -0.7596   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4551   -1.7728    0.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2631   -0.8688   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7524    1.9762    1.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    2.8385    1.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591    2.3831    1.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4385   -1.5320    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.4478    0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851   -1.8431    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7815   -2.0793    1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6715   -0.2766   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2524    1.4928   -2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1983    0.9683   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -0.0568    1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357   -1.1239   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.3873   -1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    2.0136   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    2.1880   -1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1501   -0.2761   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0403   -2.5628    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -1.7591    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7310    2.0383    1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 14 24  1  0
 24 25  2  0
 24 26  1  0
 12  5  1  0
 23 16  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  1
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
 26 42  1  0
M  END


  Mrv1652309272007312D          

 26 27  0  0  0  0            999 V2000
10000.5946 9998.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8806 9999.0041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.1646 9998.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4502 9999.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7354 9998.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0205 9999.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5888 9996.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.1612 9997.3537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4502 9999.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8806 9999.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.594610000.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.164610000.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.026710001.0676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.454810000.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.7390 9999.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.024710000.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3102 9999.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3102 9999.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0246 9998.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.7390 9999.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5901 9999.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8758 9998.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8758 9997.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5901 9997.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3045 9997.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3045 9998.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
  1 18  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 21  1  0  0  0  0
 23  8  1  0  0  0  0
 24  7  1  0  0  0  0
  6 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003572

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
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+/t16-/m1/s1

> <INCHI_KEY>
DOUMFZQKYFQNTF-WUTVXBCWSA-N

> <FORMULA>
C18H16O8

> <MOLECULAR_WEIGHT>
360.3148

> <EXACT_MASS>
360.084517488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.54956061167712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
3.004126281

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.944066768560225

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1312932183061957

> <JCHEM_PKA_STRONGEST_BASIC>
-6.28376227950831

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
90.95010000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rosemary acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003572
     RDKit          3D
Rosmarinic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.2063   -1.1387    2.5435 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5402   -0.5879    1.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970   -0.8514    1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7187   -0.2400    0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1457   -0.4290    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -1.2728    1.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2342   -1.4020    1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8837   -0.6947    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2454   -0.8172   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363    0.1448   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    0.8735   -1.5893 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    0.2936   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    0.3010    0.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422    0.5531    0.8962 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0052   -0.0385   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4530    0.1155   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798    1.2349   -1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3497    1.3330   -1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1772    0.3440   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5673    0.4560   -0.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -0.7596   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4551   -1.7728    0.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2631   -0.8688   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7524    1.9762    1.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    2.8385    1.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591    2.3831    1.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4385   -1.5320    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.4478    0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851   -1.8431    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7815   -2.0793    1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6715   -0.2766   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2524    1.4928   -2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1983    0.9683   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -0.0568    1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357   -1.1239   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.3873   -1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    2.0136   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    2.1880   -1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1501   -0.2761   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0403   -2.5628    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -1.7591    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7310    2.0383    1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 14 24  1  0
 24 25  2  0
 24 26  1  0
 12  5  1  0
 23 16  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  1
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
 26 42  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8667.7778664.036   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.4448664.808   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.1078664.036   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8663.7748664.808   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.4398664.036   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8661.1058664.808   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8658.4328660.186   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8655.7688661.727   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8663.7748666.349   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8666.4448666.349   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8667.7778667.119   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8665.1078667.119   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8670.4508668.660   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8673.1168667.119   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8671.7808666.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.4468667.118   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.1128666.348   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.1128664.808   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.4468664.038   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.7808664.808   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8658.4358664.806   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8657.1018664.036   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8657.1018662.496   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8658.4358661.727   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8659.7688662.496   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8659.7688664.036   0.000  0.00  0.00           C+0
CONECT    1    2   18                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5   26                                                       
CONECT    7   24                                                            
CONECT    8   23                                                            
CONECT    9    4                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   16                                                            
CONECT   14   15                                                            
CONECT   15   16   20   14                                                  
CONECT   16   15   17   13                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19    1                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   22   26                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24    8                                                  
CONECT   24   23   25    7                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21    6                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0003572
HETATM    1  O1  UNL     1      -0.206  -1.139   2.543  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.540  -0.588   1.711  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.997  -0.851   1.642  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.719  -0.240   0.746  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.146  -0.429   0.599  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.869  -1.273   1.393  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.234  -1.402   1.191  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.884  -0.695   0.202  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.245  -0.817  -0.006  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.136   0.145  -0.580  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.767   0.874  -1.589  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.785   0.294  -0.406  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.052   0.301   0.831  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.442   0.553   0.896  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.005  -0.038  -0.391  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.453   0.116  -0.529  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.980   1.235  -1.159  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.350   1.333  -1.263  1.00  0.00           C  
HETATM   19  C15 UNL     1      -6.177   0.344  -0.754  1.00  0.00           C  
HETATM   20  O5  UNL     1      -7.567   0.456  -0.867  1.00  0.00           O  
HETATM   21  C16 UNL     1      -5.626  -0.760  -0.132  1.00  0.00           C  
HETATM   22  O6  UNL     1      -6.455  -1.773   0.390  1.00  0.00           O  
HETATM   23  C17 UNL     1      -4.263  -0.869  -0.022  1.00  0.00           C  
HETATM   24  C18 UNL     1      -1.752   1.976   1.070  1.00  0.00           C  
HETATM   25  O7  UNL     1      -0.844   2.838   1.137  1.00  0.00           O  
HETATM   26  O8  UNL     1      -3.059   2.383   1.164  1.00  0.00           O  
HETATM   27  H1  UNL     1       2.438  -1.532   2.319  1.00  0.00           H  
HETATM   28  H2  UNL     1       2.198   0.448   0.081  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.385  -1.843   2.179  1.00  0.00           H  
HETATM   30  H4  UNL     1       6.782  -2.079   1.837  1.00  0.00           H  
HETATM   31  H5  UNL     1       8.672  -0.277  -0.744  1.00  0.00           H  
HETATM   32  H6  UNL     1       6.252   1.493  -2.176  1.00  0.00           H  
HETATM   33  H7  UNL     1       4.198   0.968  -1.038  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.868  -0.057   1.714  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.736  -1.124  -0.359  1.00  0.00           H  
HETATM   36  H10 UNL     1      -1.446   0.387  -1.259  1.00  0.00           H  
HETATM   37  H11 UNL     1      -3.360   2.014  -1.561  1.00  0.00           H  
HETATM   38  H12 UNL     1      -5.833   2.188  -1.748  1.00  0.00           H  
HETATM   39  H13 UNL     1      -8.150  -0.276  -0.489  1.00  0.00           H  
HETATM   40  H14 UNL     1      -6.040  -2.563   0.837  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.851  -1.759   0.479  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.731   2.038   1.829  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   27
CONECT    4    5   28
CONECT    5    6    6   12
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9   10
CONECT    9   31
CONECT   10   11   12   12
CONECT   11   32
CONECT   12   33
CONECT   13   14
CONECT   14   15   24   34
CONECT   15   16   35   36
CONECT   16   17   17   23
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   20   21
CONECT   20   39
CONECT   21   22   23   23
CONECT   22   40
CONECT   23   41
CONECT   24   25   25   26
CONECT   26   42
END

HMDB0003572
     RDKit          3D
Rosmarinic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.2063   -1.1387    2.5435 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5402   -0.5879    1.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970   -0.8514    1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7187   -0.2400    0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1457   -0.4290    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -1.2728    1.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2342   -1.4020    1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8837   -0.6947    0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2454   -0.8172   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363    0.1448   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667    0.8735   -1.5893 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    0.2936   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520    0.3010    0.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422    0.5531    0.8962 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0052   -0.0385   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4530    0.1155   -0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798    1.2349   -1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3497    1.3330   -1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1772    0.3440   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5673    0.4560   -0.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -0.7596   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4551   -1.7728    0.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2631   -0.8688   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7524    1.9762    1.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    2.8385    1.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0591    2.3831    1.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4385   -1.5320    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.4478    0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851   -1.8431    2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7815   -2.0793    1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6715   -0.2766   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2524    1.4928   -2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1983    0.9683   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676   -0.0568    1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357   -1.1239   -0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.3873   -1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    2.0136   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    2.1880   -1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1501   -0.2761   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0403   -2.5628    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -1.7591    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7310    2.0383    1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 14 24  1  0
 24 25  2  0
 24 26  1  0
 12  5  1  0
 23 16  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  1
 15 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
 26 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid	ChEBI
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactate	Generator
Rosmarinate	Generator
Rosemary acid	HMDB
Rosmarinic acid, (R-(e))-isomer	HMDB
(R)-Rosmarinate	HMDB
Labiatenic acid	HMDB
Labiatic acid	HMDB
Rosemaric acid	HMDB
trans-Rosmarinic acid	HMDB
(Z)-Rosmarinic acid	HMDB
Rosmarinic acid	ChEBI

Chemical Formula

C₁₈H₁₆O₈

Average Molecular Weight

360.3148

Monoisotopic Molecular Weight

360.084517488

IUPAC Name

(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid

Traditional Name

rosemary acid

CAS Registry Number

20283-92-5

SMILES

OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1

InChI Identifier

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+/t16-/m1/s1

InChI Key

DOUMFZQKYFQNTF-WUTVXBCWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
3-phenylpropanoic-acid
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

rosmarinic acid (CHEBI:50371 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15866491)

Cell

Fibroblasts (HMDB: HMDB0003572)

Excreta

Biofluid or Excreta

Urine (PMID: 15309457)

Cellular substructure

Membrane (HMDB: HMDB0003572)

Source

Exogenous

Exogenous (HMDB: HMDB0003572)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0003572)

Plant

Plant (HMDB: HMDB0003572)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0003572)
Cyclooxygenase 1 inhibitor (HMDB: HMDB0003572)
Cyclooxygenase 2 inhibitor (HMDB: HMDB0003572)
Beta inhibitor (HMDB: HMDB0003572)

Enzyme inhibitor

Lipoxygenase inhibitor (HMDB: HMDB0003572)
Adenylate-cyclase inhibitor (HMDB: HMDB0003572)
Antiintegrase (HMDB: HMDB0003572)
Deiodinase inhibitor (HMDB: HMDB0003572)

Immunomodulator (HMDB: HMDB0003572)
Apoptotic (HMDB: HMDB0003572)

Hormone antagonist (HMDB: HMDB0003572)
Calcium antagonist (HMDB: HMDB0003572)
Anti aggregant (HMDB: HMDB0003572)
Anti Alzheimeran (HMDB: HMDB0003572)
Anti anaphylactic (HMDB: HMDB0003572)
Anti atherosclerotic (HMDB: HMDB0003572)
Anti bacterial (HMDB: HMDB0003572)
Anti complementary (HMDB: HMDB0003572)
Anti depressant (HMDB: HMDB0003572)
Anti edemic (HMDB: HMDB0003572)
Anti gonadotropic (HMDB: HMDB0003572)
Anti hemolytic (HMDB: HMDB0003572)
Anti hepatotoxic (HMDB: HMDB0003572)
Anti herpetic (HMDB: HMDB0003572)
Anti HIV (HMDB: HMDB0003572)
Anti hyperthyroid (HMDB: HMDB0003572)
Anti-inflammatory (HMDB: HMDB0003572)
Anti leukotriene (HMDB: HMDB0003572)
Anti lipoperoxidant (HMDB: HMDB0003572)
Anti mutagenic (HMDB: HMDB0003572)
Anti nephritic (HMDB: HMDB0003572)
Anti plaque (HMDB: HMDB0003572)
Anti proliferant (HMDB: HMDB0003572)
Anti proteolytic (HMDB: HMDB0003572)
Anti pulmonotic (HMDB: HMDB0003572)
Anti radicular (HMDB: HMDB0003572)
Anti shock (HMDB: HMDB0003572)
Anti thyreotropic (HMDB: HMDB0003572)
Anti thyroid (HMDB: HMDB0003572)
Anti uremic (HMDB: HMDB0003572)
Anxiolytic (HMDB: HMDB0003572)
Cytotoxic (HMDB: HMDB0003572)

Industrial application

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	694.71 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1425 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.871 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	170.259	30932474
[M-H]-	Not Available	171.7	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000437
[M+H]+	Not Available	169.157	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000437

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	2.57	ALOGPS
logP	3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.95 m³·mol⁻¹	ChemAxon
Polarizability	34.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	182.203	30932474
DeepCCS	[M-H]-	179.808	30932474
DeepCCS	[M-2H]-	213.001	30932474
DeepCCS	[M+Na]+	188.188	30932474
AllCCS	[M+H]+	182.2	32859911
AllCCS	[M+H-H2O]+	179.3	32859911
AllCCS	[M+NH4]+	184.9	32859911
AllCCS	[M+Na]+	185.6	32859911
AllCCS	[M-H]-	181.2	32859911
AllCCS	[M+Na-2H]-	181.1	32859911
AllCCS	[M+HCOO]-	181.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.56 minutes	32390414
Predicted by Siyang on May 30, 2022	10.998 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	55.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1457.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	191.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	101.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	136.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	526.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	349.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	419.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	773.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	386.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1225.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	438.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	248.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	217.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rosmarinic acid	OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1	6002.2	Standard polar	33892256
Rosmarinic acid	OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1	3504.5	Standard non polar	33892256
Rosmarinic acid	OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1	3617.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rosmarinic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	3588.1	Semi standard non polar	33892256
Rosmarinic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)=CC=C1O	3532.2	Semi standard non polar	33892256
Rosmarinic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)C=C1O	3514.5	Semi standard non polar	33892256
Rosmarinic acid,1TMS,isomer #4	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O)=C2)C(=O)O)=CC=C1O	3521.1	Semi standard non polar	33892256
Rosmarinic acid,1TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O)=C2)C(=O)O)C=C1O	3519.4	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	3402.7	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #10	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O)=C2)C(=O)O)C=C1O[Si](C)(C)C	3460.1	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	3419.1	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	3406.4	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	3416.3	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)O)C=C1O	3421.2	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #6	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)O)=CC=C1O	3427.9	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #7	C[Si](C)(C)OC1=CC=C(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)C=C1O[Si](C)(C)C	3459.8	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #8	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O[Si](C)(C)C)C(O)=C2)C(=O)O)C=C1O	3418.5	Semi standard non polar	33892256
Rosmarinic acid,2TMS,isomer #9	C[Si](C)(C)OC1=CC=C(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)O)C=C1O	3418.8	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	3359.6	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #10	C[Si](C)(C)OC1=CC=C(C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)O)C=C1O	3402.5	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	3352.6	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	3364.6	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	3341.8	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	3357.1	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #6	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3351.6	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #7	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)O)C=C1O	3399.5	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #8	C[Si](C)(C)OC1=CC(C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)O)=CC=C1O	3400.0	Semi standard non polar	33892256
Rosmarinic acid,3TMS,isomer #9	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@H](CC2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)O)=CC=C1O	3411.3	Semi standard non polar	33892256
Rosmarinic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	3384.6	Semi standard non polar	33892256
Rosmarinic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	3398.3	Semi standard non polar	33892256
Rosmarinic acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3386.7	Semi standard non polar	33892256
Rosmarinic acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3378.6	Semi standard non polar	33892256
Rosmarinic acid,4TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)O)C=C1O[Si](C)(C)C	3442.5	Semi standard non polar	33892256
Rosmarinic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3424.6	Semi standard non polar	33892256
Rosmarinic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	3891.6	Semi standard non polar	33892256
Rosmarinic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)=CC=C1O	3850.7	Semi standard non polar	33892256
Rosmarinic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)C=C1O	3831.7	Semi standard non polar	33892256
Rosmarinic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O)=C2)C(=O)O)=CC=C1O	3847.7	Semi standard non polar	33892256
Rosmarinic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O)=C2)C(=O)O)C=C1O	3841.6	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	3984.7	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O)=C2)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	4023.4	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	3986.6	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	3980.6	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	3982.4	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)C=C1O	4057.9	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@H](CC2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)=CC=C1O	4051.7	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	3996.2	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(=O)O)C=C1O	4061.4	Semi standard non polar	33892256
Rosmarinic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)C=C1O	4055.8	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O)C(O)=C1	4121.1	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)C=C1O	4255.2	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	4191.4	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	4181.1	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	4164.9	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	4157.2	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	4117.8	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)C=C1O	4249.4	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC(C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)=CC=C1O	4229.9	Semi standard non polar	33892256
Rosmarinic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)=CC=C1O	4231.4	Semi standard non polar	33892256
Rosmarinic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	4337.7	Semi standard non polar	33892256
Rosmarinic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	4330.8	Semi standard non polar	33892256
Rosmarinic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	4350.6	Semi standard non polar	33892256
Rosmarinic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	4318.5	Semi standard non polar	33892256
Rosmarinic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	4388.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Rosmarinic acid GC-MS (5 TMS)	splash10-00kb-1889000000-a18403fdf27acdd9420a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Rosmarinic acid GC-MS (Non-derivatized)	splash10-00kb-1889000000-a18403fdf27acdd9420a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmarinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03k9-0900000000-0bfd48de4c7d7947465f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmarinic acid GC-MS (4 TMS) - 70eV, Positive	splash10-0a59-6429037000-febdf15ccc07a12300c9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosmarinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid LC-ESI-QTOF , negative-QTOF	splash10-03di-0901000000-f29409b402b063dcbebd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid LC-ESI-QTOF , negative-QTOF	splash10-0bt9-0907000100-ececf6d2ede2e8193b9b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid LC-ESI-QTOF , negative-QTOF	splash10-03e9-0900000000-14bb8ce94558a85b706c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid LC-ESI-QTOF , negative-QTOF	splash10-03di-0902000000-f3cc2fa86fc00ea8e474	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid LC-ESI-QTOF , negative-QTOF	splash10-03di-0900000000-0dac983721970230a210	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid LC-ESI-QTOF , positive-QTOF	splash10-001i-0439000000-38b13aa5bfab28c4d0c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid LC-ESI-QTOF , positive-QTOF	splash10-03di-0900000000-383db44d2370c9662666	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid LC-ESI-QTOF , positive-QTOF	splash10-008i-0679000000-629ad81e5a4aa4a45cd9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid , positive-QTOF	splash10-03di-0900000000-f099de2a6e6ab011d21b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid , positive-QTOF	splash10-03di-0900000000-529a6653ec4eebdd8eeb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 40V, Negative-QTOF	splash10-0239-1900000000-8bed95d3ae91d9873e98	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 10V, Negative-QTOF	splash10-03di-0902000000-36563722d30feeb69ae3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 20V, Negative-QTOF	splash10-03di-0900000000-d32896fadf8e7c5c5fa4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 40V, Negative-QTOF	splash10-01qi-0920000000-d260d2efdd9728ef5c32	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 20V, Negative-QTOF	splash10-03di-0901000000-c16c277f268b2702b889	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 10V, Positive-QTOF	splash10-03di-0900000000-78c63d5f30f84af872c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 20V, Positive-QTOF	splash10-03di-0900000000-5952242833f0961865d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 10V, Negative-QTOF	splash10-08fr-0904000000-1e0e6099d149a663ad7e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosmarinic acid 40V, Positive-QTOF	splash10-000i-2900000000-7836cebf0e5a43bbc84f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmarinic acid 10V, Positive-QTOF	splash10-03di-0819000000-20e9707f2681dfaa1a77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmarinic acid 20V, Positive-QTOF	splash10-03di-0902000000-a28b547c92e2012a4b54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmarinic acid 40V, Positive-QTOF	splash10-05gi-2900000000-7a9099cde66c5c7e5309	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmarinic acid 10V, Negative-QTOF	splash10-0a6r-0917000000-020d7427c4eb0534eba7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmarinic acid 20V, Negative-QTOF	splash10-004i-0901000000-2beb88c288aa75c18319	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosmarinic acid 40V, Negative-QTOF	splash10-03fr-0900000000-a99d2e96b7197132aef0	2016-08-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Fibroblasts

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.38 (0.0055 - 5.55) uM	Adult (>18 years old)	Both	Normal	15866491	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 461	15309457	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 461	15309457	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Rosmarinic_acid

METLIN ID

6960

PubChem Compound

5281792

PDB ID

Not Available

ChEBI ID

50371

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1372331

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Haapalainen AM, Merilainen G, Pirila PL, Kondo N, Fukao T, Wierenga RK: Crystallographic and kinetic studies of human mitochondrial acetoacetyl-CoA thiolase: the importance of potassium and chloride ions for its structure and function. Biochemistry. 2007 Apr 10;46(14):4305-21. Epub 2007 Mar 20. [PubMed:17371050 ]
Fukao T, Nakamura H, Song XQ, Nakamura K, Orii KE, Kohno Y, Kano M, Yamaguchi S, Hashimoto T, Orii T, Kondo N: Characterization of N93S, I312T, and A333P missense mutations in two Japanese families with mitochondrial acetoacetyl-CoA thiolase deficiency. Hum Mutat. 1998;12(4):245-54. [PubMed:9744475 ]
Fukao T, Zhang GX, Sakura N, Kubo T, Yamaga H, Hazama A, Kohno Y, Matsuo N, Kondo M, Yamaguchi S, Shigematsu Y, Kondo N: The mitochondrial acetoacetyl-CoA thiolase (T2) deficiency in Japanese patients: urinary organic acid and blood acylcarnitine profiles under stable conditions have subtle abnormalities in T2-deficient patients with some residual T2 activity. J Inherit Metab Dis. 2003;26(5):423-31. [PubMed:14518824 ]
Fukao T, Kodama A, Aoyanagi N, Tsukino R, Uemura S, Song XQ, Watanebe H, Kuhara T, Matsumoto I, Orii T, Kondo N: Mild form of beta-ketothiolase deficiency (mitochondrial acetoacetyl-CoA thiolase deficiency) in two Japanese siblings: identification of detectable residual activity and cross-reactive material in EB-transformed lymphocytes. Clin Genet. 1996 Oct;50(4):263-6. [PubMed:9001814 ]
Li X, Yu C, Cai Y, Liu G, Jia J, Wang Y: Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):41-7. Epub 2005 Apr 19. [PubMed:15866491 ]
Sahu A, Rawal N, Pangburn MK: Inhibition of complement by covalent attachment of rosmarinic acid to activated C3b. Biochem Pharmacol. 1999 Jun 15;57(12):1439-46. [PubMed:10353266 ]
Lee J, Jung E, Kim Y, Lee J, Park J, Hong S, Hyun CG, Park D, Kim YS: Rosmarinic acid as a downstream inhibitor of IKK-beta in TNF-alpha-induced upregulation of CCL11 and CCR3. Br J Pharmacol. 2006 Jun;148(3):366-75. [PubMed:16604092 ]
Petersen M, Simmonds MS: Rosmarinic acid. Phytochemistry. 2003 Jan;62(2):121-5. [PubMed:12482446 ]
Baba S, Osakabe N, Natsume M, Terao J: Orally administered rosmarinic acid is present as the conjugated and/or methylated forms in plasma, and is degraded and metabolized to conjugated forms of caffeic acid, ferulic acid and m-coumaric acid. Life Sci. 2004 May 28;75(2):165-78. [PubMed:15120569 ]
Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Showing metabocard for Rosmarinic acid (HMDB0003572)

MOL for HMDB0003572 (Rosmarinic acid)

3D MOL for HMDB0003572 (Rosmarinic acid)

3D SDF for HMDB0003572 (Rosmarinic acid)

3D-SDF for HMDB0003572 (Rosmarinic acid)

PDB for HMDB0003572 (Rosmarinic acid)

3D PDB for HMDB0003572 (Rosmarinic acid)

SMILES for HMDB0003572 (Rosmarinic acid)

INCHI for HMDB0003572 (Rosmarinic acid)

Structure for HMDB0003572 (Rosmarinic acid)

3D Structure for HMDB0003572 (Rosmarinic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra