NP-MRD: Showing NP-Card for Rosmarinic acid (NP0002831)

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Record Information

Version

2.0

Created at

2020-11-23 19:41:32 UTC

Updated at

2021-08-19 23:59:27 UTC

NP-MRD ID

NP0002831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rosmarinic acid

Provided By

BMRB

Description

Rosmarinic acid, also known as rosmarinate, 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. Rosmarinic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Rosmarinic acid is found in Ajuga decumbens, Anchusa officinalis, Anchusa strigosa, Foeniculum vulgare , Anthoceros punctatus, Apis cerana, Centella asiatica , Clinopodium chinense, Clinopodium umbrosum, Plectranthus amboinicus, Plectranthus scutellarioides, Colocasia esculenta , Condea verticillata, Coriandrum sativum, Crataegus laevigata, Ehretia microphylla, Verbena bipinnatifida, Glechoma hederacea, Hedeoma drummondii, Hedera hibernica, Heliotropium arborescens, Hyptis capitata, Isodon coetsa, Isodon japonicus, Isodon oresbius, Isodon sculponeatus, Lavandula angustifolia, Lavandula intermedia, Lithospermum erythrorhizon, Lycopus asper, Lycopus europaeus, Mosla dianthera, Oceaniopteris gibba, Ocimum americanum, Ocimum gratissimum, Ocimum tenuiflorum, Origanum acutidens, Perilla frutescens, Plantago lagopus, Coleus forskohlii, Prunella vulgaris, Robdosia coetsa, Salvia amplexicaulis, Salvia deserta, Salvia fruticosa, Salvia przewalskii, Salvia trijuga, Thymus austriacus, Thymus capitatus , Thymus citriodorus , Thymus longicaulis , Thymus oblongifolius, Thymus praecox , Thymus pulegioides , Thymus serpyllum , Thymus sibthorpii, Trigonotis peduncularis, Triumfetta rhomboidea, Vaccinium arctostaphylos, Verbena hybrida, Veronica spicata and Zataria multiflora. Rosmarinic acid was first documented in 1999 (PMID: 10353266). Based on a literature review a small amount of articles have been published on Rosmarinic acid (PMID: 15866491) (PMID: 16604092) (PMID: 12482446).

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

NP0002831
     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    0.0436   -1.5742   -2.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052   -0.9858   -1.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497   -0.7553   -1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.1405   -0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.1224   -0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9995   -0.2232   -1.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3471    0.0497   -1.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8746    0.7010   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2443    0.9803   -0.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    1.0662    0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6171    1.7288    1.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.7855    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1370   -0.5814   -0.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5527   -0.8032   -0.1915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1688    0.5599   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416    0.4948    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    0.4977   -1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7459    0.4428   -1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4100    0.3842    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7958    0.3298    0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.3827    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297    0.3263    2.5621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2572    0.4385    1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7791   -1.6669    0.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9139   -2.0653    1.3566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -2.1078    1.7978 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6128   -1.0875   -2.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1023    0.1745    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803   -0.7474   -2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324   -0.2689   -2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6533    1.4595    0.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0537    2.0194    2.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0782    1.0930    1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9242   -1.3319   -1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216    1.0493    0.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8494    1.1382   -0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8611    0.5438   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3575    0.4432   -1.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3097    0.2867    1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2175    0.2849    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6688    0.4401    2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815   -1.4675    2.2559 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  6
 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>
NP0002831

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

NP0002831
     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    0.0436   -1.5742   -2.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052   -0.9858   -1.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497   -0.7553   -1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.1405   -0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.1224   -0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9995   -0.2232   -1.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3471    0.0497   -1.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8746    0.7010   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2443    0.9803   -0.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    1.0662    0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6171    1.7288    1.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.7855    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1370   -0.5814   -0.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5527   -0.8032   -0.1915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1688    0.5599   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416    0.4948    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    0.4977   -1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7459    0.4428   -1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4100    0.3842    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7958    0.3298    0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.3827    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297    0.3263    2.5621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2572    0.4385    1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7791   -1.6669    0.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9139   -2.0653    1.3566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -2.1078    1.7978 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6128   -1.0875   -2.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1023    0.1745    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803   -0.7474   -2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324   -0.2689   -2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6533    1.4595    0.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0537    2.0194    2.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0782    1.0930    1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9242   -1.3319   -1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216    1.0493    0.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8494    1.1382   -0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8611    0.5438   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3575    0.4432   -1.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3097    0.2867    1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2175    0.2849    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6688    0.4401    2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815   -1.4675    2.2559 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  6
 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    NP0002831
HETATM    1  O1  UNL     1       0.044  -1.574  -2.322  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.605  -0.986  -1.374  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.050  -0.755  -1.469  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.719  -0.140  -0.510  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.139   0.122  -0.532  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.000  -0.223  -1.542  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.347   0.050  -1.517  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.875   0.701  -0.432  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.244   0.980  -0.402  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.033   1.066   0.610  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.617   1.729   1.696  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.685   0.785   0.569  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.137  -0.581  -0.293  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.553  -0.803  -0.191  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.169   0.560  -0.079  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.642   0.495   0.036  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.381   0.498  -1.130  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.746   0.443  -1.057  1.00  0.00           C  
HETATM   19  C15 UNL     1      -6.410   0.384   0.159  1.00  0.00           C  
HETATM   20  O5  UNL     1      -7.796   0.330   0.181  1.00  0.00           O  
HETATM   21  C16 UNL     1      -5.654   0.383   1.302  1.00  0.00           C  
HETATM   22  O6  UNL     1      -6.230   0.326   2.562  1.00  0.00           O  
HETATM   23  C17 UNL     1      -4.257   0.439   1.241  1.00  0.00           C  
HETATM   24  C18 UNL     1      -1.779  -1.667   0.990  1.00  0.00           C  
HETATM   25  O7  UNL     1      -2.914  -2.065   1.357  1.00  0.00           O  
HETATM   26  O8  UNL     1      -0.712  -2.108   1.798  1.00  0.00           O  
HETATM   27  H1  UNL     1       2.613  -1.088  -2.339  1.00  0.00           H  
HETATM   28  H2  UNL     1       2.102   0.175   0.347  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.580  -0.747  -2.417  1.00  0.00           H  
HETATM   30  H4  UNL     1       6.932  -0.269  -2.368  1.00  0.00           H  
HETATM   31  H5  UNL     1       8.653   1.460   0.389  1.00  0.00           H  
HETATM   32  H6  UNL     1       6.054   2.019   2.484  1.00  0.00           H  
HETATM   33  H7  UNL     1       4.078   1.093   1.407  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.924  -1.332  -1.094  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.722   1.049   0.829  1.00  0.00           H  
HETATM   36  H10 UNL     1      -1.849   1.138  -0.964  1.00  0.00           H  
HETATM   37  H11 UNL     1      -3.861   0.544  -2.090  1.00  0.00           H  
HETATM   38  H12 UNL     1      -6.357   0.443  -1.949  1.00  0.00           H  
HETATM   39  H13 UNL     1      -8.310   0.287   1.037  1.00  0.00           H  
HETATM   40  H14 UNL     1      -7.218   0.285   2.675  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.669   0.440   2.147  1.00  0.00           H  
HETATM   42  H16 UNL     1      -0.082  -1.467   2.256  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

NP0002831
     RDKit          3D

42 43  0  0  0  0  0  0  0  0999 V2000
    0.0436   -1.5742   -2.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052   -0.9858   -1.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497   -0.7553   -1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.1405   -0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    0.1224   -0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9995   -0.2232   -1.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3471    0.0497   -1.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8746    0.7010   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2443    0.9803   -0.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327    1.0662    0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6171    1.7288    1.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.7855    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1370   -0.5814   -0.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5527   -0.8032   -0.1915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1688    0.5599   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416    0.4948    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    0.4977   -1.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7459    0.4428   -1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4100    0.3842    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7958    0.3298    0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.3827    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297    0.3263    2.5621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2572    0.4385    1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7791   -1.6669    0.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9139   -2.0653    1.3566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -2.1078    1.7978 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6128   -1.0875   -2.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1023    0.1745    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803   -0.7474   -2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324   -0.2689   -2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6533    1.4595    0.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0537    2.0194    2.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0782    1.0930    1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9242   -1.3319   -1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216    1.0493    0.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8494    1.1382   -0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8611    0.5438   -2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3575    0.4432   -1.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3097    0.2867    1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2175    0.2849    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6688    0.4401    2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815   -1.4675    2.2559 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  6
 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

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	MeSH, HMDB
Rosmarinic acid	ChEBI
(R)-Rosmarinate	Generator, HMDB
Labiatenic acid	HMDB
Labiatic acid	HMDB
Rosemaric acid	HMDB
trans-Rosmarinic acid	HMDB
(Z)-Rosmarinic acid	PhytoBank, HMDB

Chemical Formula

C₁₈H₁₆O₈

Average Mass

360.3148 Da

Monoisotopic Mass

360.08452 Da

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

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, methanol, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	FooDB
Actinidia chinensis	FooDB	FooDB
Agaricus bisporus	FooDB	FooDB
Agastache rugosa	KNApSAcK Database	22123792
Agave	FooDB	FooDB
Ajuga decumbens	LOTUS Database	35616633
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	FooDB
Allium cepa L.	FooDB	FooDB
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	FooDB
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	FooDB	FooDB
Ananas comosus	FooDB	FooDB
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anchusa officinalis	LOTUS Database	35616633
Anchusa strigosa	LOTUS Database	35616633
Anethum foeniculum	Plant	KNApSAcK
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anethum spp.	KNApSAcK Database	22123792
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anser anser	FooDB	FooDB
Anthoceros punctatus	LOTUS Database	35616633
Anthriscus cerefolium	FooDB	FooDB
Anthurium versicolor	KNApSAcK Database	22123792
Apeiba tibourbou	KNApSAcK Database	22123792
Apis cerana	LOTUS Database	35616633
Apium graveolens	FooDB	FooDB
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Arachis hypogaea	FooDB	FooDB
Arctium lappa	FooDB	FooDB
Armoracia rusticana	FooDB	FooDB
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	FooDB	FooDB
Astrantia major	KNApSAcK Database	22123792
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Basella alba	FooDB	FooDB
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	FooDB
Bison bison	FooDB	FooDB
Borago officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	FooDB
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	FooDB
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	PHENOL EXPLORER
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Centella asiatica	Plant	KNApSAcK
Ceratonia siliqua	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	PHENOL EXPLORER
Cirsium	FooDB	FooDB
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	FooDB
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	FooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	FooDB
Clinopodium chinense	LOTUS Database	35616633
Clinopodium chinense var. parviflorum	KNApSAcK Database	22123792
Clinopodium umbrosum	LOTUS Database	35616633
Cocos nucifera	FooDB	FooDB
Coffea arabica L.	FooDB	FooDB
Coffea canephora	FooDB	FooDB
Coleus amboinicus	LOTUS Database	35616633
Coleus blumei	LOTUS Database	35616633
Coleus forskohlii	KNApSAcK Database	22123792
Colocasia esculenta	Plant	KNApSAcK
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Condea verticillata	LOTUS Database	35616633
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum	LOTUS Database	35616633
Coriandrum sativum L.	FooDB	FooDB
Corylus	FooDB	FooDB
Corylus avellana	FooDB	FooDB
Crataegus laevigata	LOTUS Database	35616633
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	FooDB
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	PHENOL EXPLORER
Curcuma longa	FooDB	FooDB
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Daucus carota	FooDB	FooDB
Daucus carota ssp. sativus	FooDB	FooDB
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Ehretia microphylla	LOTUS Database	35616633
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Elsholtzia rugulosa Hemsl.	KNApSAcK Database	22123792
Empetrum nigrum	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eragrostis tef	FooDB	FooDB
Eriobotrya japonica	FooDB	FooDB
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Eucalyptus globulus	KNApSAcK Database	22123792
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	FooDB
Fragaria x ananassa	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Garcinia mangostana	FooDB	FooDB
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	FooDB
Glandularia bipinnatifida	Plant	KNApSAcK
Glechoma hederacea	LOTUS Database	35616633
Glycine max	FooDB	FooDB
Gossypium	FooDB	FooDB
Grifola frondosa	FooDB	FooDB
Hamelia patens	KNApSAcK Database	22123792
Hedeoma drummondii	LOTUS Database	35616633
Hedera helix	KNApSAcK Database	22123792
Hedera hibernica	LOTUS Database	35616633
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Helicteres angustifolia	KNApSAcK Database	22123792
Helicteres isora	KNApSAcK Database	22123792
Helicteres isora L.	KNApSAcK Database	22123792
Heliotropium arborescens	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Hordeum vulgare	FooDB	FooDB
Hyptis capitata	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Illicium verum	FooDB	PHENOL EXPLORER
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Isodon coetsa	LOTUS Database	35616633
Isodon japonicus	LOTUS Database	35616633
Isodon oresbius	LOTUS Database	35616633
Isodon sculponeatus	LOTUS Database	35616633
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	FooDB
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	FooDB
Lagenaria siceraria	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	PHENOL EXPLORER
Lavandula angustifolia	LOTUS Database	35616633
Lavandula intermedia	LOTUS Database	35616633
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Levisticum officinale	FooDB	FooDB
Ligusticum spp.	KNApSAcK Database	22123792
Lindelofia stylosa	KNApSAcK Database	22123792
Linum usitatissimum	FooDB	FooDB
Litchi chinensis	FooDB	FooDB
Lithospermum erythrorhizon	LOTUS Database	35616633
Lithospermum ruderale	KNApSAcK Database	22123792
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Lycopus asper	LOTUS Database	35616633
Lycopus europaeus	LOTUS Database	35616633
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	FooDB
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Melissa officinalis	KNApSAcK Database	22123792
Melissa officinalis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha	FooDB	PHYTOHUB
Mentha aquatica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha arvensis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha haplocalyx	KNApSAcK Database	22123792
Mentha piperita	KNApSAcK Database	22123792
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Momordica balsamina	KNApSAcK Database	22123792
Momordica charantia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mosla dianthera	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	PHENOL EXPLORER
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nepeta cadmea	KNApSAcK Database	22123792
Nephelium lappaceum	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Nuphar lutea	FooDB	FooDB
Oceaniopteris gibba	LOTUS Database	35616633
Ocimum americanum	LOTUS Database	35616633
Ocimum basilicum	KNApSAcK Database	22123792
Ocimum gratissimum	LOTUS Database	35616633
Ocimum tenuiflorum	LOTUS Database	35616633
Odocoileus	FooDB	FooDB
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum acutidens	Plant	KNApSAcK
Origanum majorana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum X majoricum	FooDB	PHENOL EXPLORER
Orthosiphon stamineus	KNApSAcK Database	22123792
Oryctolagus	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Ovis aries	FooDB	FooDB
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pediomelum esculentum	FooDB	FooDB
Perideridia oregana	FooDB	FooDB
Perilla frutescens	LOTUS Database	35616633
Perilla frutescens var.acuta.	KNApSAcK Database	22123792
Persea americana	FooDB	FooDB
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	FooDB	FooDB
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	FooDB
Pinus edulis	FooDB	FooDB
Piper nigrum L.	FooDB	PHENOL EXPLORER
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Plantago lagopus	LOTUS Database	35616633
Plectranthus barbatus	Plant	KNApSAcK
Pleurotus ostreatus	FooDB	FooDB
Polygonum alpinum	FooDB	FooDB
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Prunella vulgaris	LOTUS Database	35616633
Prunus armeniaca	FooDB	FooDB
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	FooDB
Prunus persica	FooDB	FooDB
Prunus persica var. nucipersica	FooDB	FooDB
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Punica granatum	FooDB	FooDB
Pyrus communis	FooDB	FooDB
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Rheum rhabarbarum	FooDB	FooDB
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	FooDB
Robdosia coetsa	-	KNApSAcK
Rosa	FooDB	FooDB
Rosmarinus officinalis	KNApSAcK Database	22123792
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salvia amplexicaulis	LOTUS Database	35616633
Salvia bowleyana	KNApSAcK Database	22123792
Salvia cavaleriei	KNApSAcK Database	22123792
Salvia chinensis	KNApSAcK Database	22123792
Salvia deserta	LOTUS Database	35616633
Salvia elegans	FooDB	FooDB
Salvia flava	KNApSAcK Database	22123792
Salvia fruticosa	LOTUS Database	35616633
Salvia hispanica	FooDB	FooDB
Salvia lavandulifolia	KNApSAcK Database	22123792
Salvia miltiorrhiza	KNApSAcK Database	22123792
Salvia officinalis	KNApSAcK Database	22123792
Salvia prionitis	KNApSAcK Database	22123792
Salvia przewalskii	LOTUS Database	35616633
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia sonchifolia	KNApSAcK Database	22123792
Salvia trijuga	LOTUS Database	35616633
Salvia Yunnanensis	KNApSAcK Database	22123792
Salvinia molesta	KNApSAcK Database	22123792
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Sanicula europaea	KNApSAcK Database	22123792
Sanicula spp.	KNApSAcK Database	22123792
Sarcandra glabra	KNApSAcK Database	22123792
Satureja hortensis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Satureja montana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Satureja subspicata	KNApSAcK Database	22123792
Scorzonera hispanica	FooDB	FooDB
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Sinapis alba	FooDB	FooDB
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	FooDB
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	FooDB
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Spinacia oleracea	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Symphytum officinale	KNApSAcK Database	22123792
Syzygium aromaticum	FooDB	PHENOL EXPLORER
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Taraxacum officinale	FooDB	FooDB
Tetragonia tetragonioides	FooDB	FooDB
Teucrium scorodonia	KNApSAcK Database	22123792
Thalassia hemprichii	KNApSAcK Database	22123792
Thelesperma	FooDB	FooDB
Thymus austriacus	Plant	KNApSAcK
Thymus capitatus	Plant	KNApSAcK
Thymus citriodorus	Plant	KNApSAcK
Thymus longicaulis	Plant	KNApSAcK
Thymus oblongifolius	Plant	KNApSAcK
Thymus praecox	Plant	KNApSAcK
Thymus pulegioides	Plant	KNApSAcK
Thymus serpyllum	Plant	KNApSAcK
Thymus sibthorpii	Plant	KNApSAcK
Thymus vulgaris	KNApSAcK Database	22123792
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tournefortia sarmentosa	KNApSAcK Database	22123792
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	FooDB
Trigonotis peduncularis	LOTUS Database	35616633
Triticum	FooDB	FooDB
Triticum aestivum	FooDB	FooDB
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Triumfetta rhomboidea	LOTUS Database	35616633
Typha angustifolia	FooDB	FooDB
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium arctostaphylos	LOTUS Database	35616633
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena hybrida	Plant	KNApSAcK
Verbena officinalis	FooDB	FooDB
Veronica spicata	Plant	KNApSAcK
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	FooDB
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	FooDB
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	FooDB
Xanthosoma sagittifolium	FooDB	FooDB
Zataria multiflora	LOTUS Database	35616633
Zea mays L.	FooDB	FooDB
Zingiber officinale	FooDB	PHENOL EXPLORER
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB
Zostera marina	KNApSAcK Database	22123792
Zostera noltii	KNApSAcK Database	22123792

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0003572

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB 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

Good Scents ID

rw1372331

References

General References

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. doi: 10.1016/s0006-2952(99)00044-1. [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. doi: 10.1038/sj.bjp.0706728. [PubMed:16604092 ]
Petersen M, Simmonds MS: Rosmarinic acid. Phytochemistry. 2003 Jan;62(2):121-5. doi: 10.1016/s0031-9422(02)00513-7. [PubMed:12482446 ]

Showing NP-Card for Rosmarinic acid (NP0002831)

MOL for NP0002831 (Rosmarinic acid)

3D MOL for NP0002831 (Rosmarinic acid)

3D SDF for NP0002831 (Rosmarinic acid)

3D-SDF for NP0002831 (Rosmarinic acid)

PDB for NP0002831 (Rosmarinic acid)

3D PDB for NP0002831 (Rosmarinic acid)

SMILES for NP0002831 (Rosmarinic acid)

INCHI for NP0002831 (Rosmarinic acid)

Structure for NP0002831 (Rosmarinic acid)

3D Structure for NP0002831 (Rosmarinic acid)