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Showing NP-Card for Methyl caffeate (NP0051568)

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Record Information
Version2.0
Created at2022-04-27 22:53:02 UTC
Updated at2022-04-27 22:53:03 UTC
NP-MRD IDNP0051568
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl caffeate
DescriptionMethyl caffeate 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. Methyl caffeate is found in Abutilon indicum , Actaea racemosa , Ageratina adenophora, Alangium platanifolium, Angelica japonica, Artemisia apiacea , Artemisia assoana, Artemisia santolinifolia, Balanophora harlandii, Balanophora japonica, Balanophora tobiracola, Bedfordia salicina, Berberis fendleri, Campanula alata, Cestrum parqui, Chaerophyllum hirsutum, Chrysanthemum morifolium, Cyanthillium cinereum, Daphne feddei, Erigeron breviscapus, Fagraea gracilipes, Fumaria parviflora, Gaillardia pulchella, Gochnatra rusbyana, Haplopteris anguste-elongata, Hibiscus taiwanensis, Hypericum ascyron, Pharbitis nil , Isodon coetsa, Isodon umbrosus, Kigelia africana, Koyamasia calcarea, Larix kaempferi, Lespedeza bicolor , Lonicera bournei, Magnolia obovata, Marshallia obovata, Meehania urticifolia, Melissa officinalis, Meum athamanticum, Oenothera speciosa, Perilla frutescens, Persicaria perfoliata, Pertya glabrescens, Petasites formosanus, Petasites pyrenaicus, Phellodendron amurense , Phellodendron chinense, Phellodendron japonicum MAXIM, Plantago major, Prunus domestica, Pseudostiffita kingii, Lobaria virens, Salvia divinorum, Scorzonera hispanica, Scorzonera laciniata, Sideritis lotsyi, Smilax bracteata, Solanum torvum, Solanum tuberosum , Stereospermum acuminatissimum, Tanacetum odessanum, Vittaria anguste-elongata and Xanthium strumarium. Methyl caffeate was first documented in 2011 (PMID: 21963451). Based on a literature review very few articles have been published on methyl caffeate.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051568 (Methyl caffeate)


  Mrv1652304282200532D          

 14 14  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 13  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
Download

3D MOL for NP0051568 (Methyl caffeate)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    5.3906    0.0832    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -0.4074   -0.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    0.3605    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.4737    0.6962 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155   -0.1255   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628    0.5790    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8329    0.1366    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1609   -1.0677   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -1.4995   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4926   -0.6569   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7641   -1.0919   -0.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2020    0.5563    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    1.4509    0.6812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8794    0.9480    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9730    0.0817   -0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -0.7050    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000    1.0519    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053   -1.0865   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7464    1.5416    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638   -1.7202   -0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7004   -2.4447   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583   -0.5563   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1463    1.1844    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6289    1.9139    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7 14  2  0
 14 12  1  0
 12 13  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  6 19  1  0
 14 24  1  0
 13 23  1  0
 11 22  1  0
  9 21  1  0
  8 20  1  0
M  END
Download

3D SDF for NP0051568 (Methyl caffeate)


  Mrv1652304282200532D          

 14 14  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 13  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+

> <INCHI_KEY>
OCNYGKNIVPVPPX-HWKANZROSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.186

> <EXACT_MASS>
194.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.508921312006116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
1.9081830060000002

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.612516670704302

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208666078240437

> <JCHEM_PKA_STRONGEST_BASIC>
-6.28375908925548

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
51.790800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl caffeate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0051568 (Methyl caffeate)

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PDB for NP0051568 (Methyl caffeate)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    2                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0051568 (Methyl caffeate)
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SMILES for NP0051568 (Methyl caffeate)
COC(=O)\C=C\C1=CC(O)=C(O)C=C1
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INCHI for NP0051568 (Methyl caffeate)
InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+
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View in JSmol
Synonyms
ValueSource
Caffeic acid, methyl esterChEBI
Caffeate, methyl esterGenerator
Methyl caffeic acidGenerator
Chemical FormulaC10H10O4
Average Mass194.1860 Da
Monoisotopic Mass194.05791 Da
IUPAC Namemethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Namemethyl caffeate
CAS Registry NumberNot Available
SMILES
COC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+
InChI KeyOCNYGKNIVPVPPX-HWKANZROSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abutilon indicumPlant
Actaea racemosaPlant
Ageratina adenophoraLOTUS Database
Alangium platanifoliumLOTUS Database
Angelica japonicaLOTUS Database
Artemisia apiaceaPlant
Artemisia assoanaLOTUS Database
Artemisia santolinifoliaLOTUS Database
Balanophora harlandiiLOTUS Database
Balanophora japonicaLOTUS Database
Balanophora tobiracolaLOTUS Database
Bedfordia salicinaPlant
Berberis fendleriLOTUS Database
Campanula alataLOTUS Database
Cestrum parquiLOTUS Database
Chaerophyllum hirsutumPlant
Chrysanthemum morifoliumLOTUS Database
Cyanthillium cinereumLOTUS Database
Daphne feddeiPlant
Erigeron breviscapusLOTUS Database
Fagraea gracilipesLOTUS Database
Fumaria parvifloraLOTUS Database
Gaillardia pulchellaPlant
Gochnatra rusbyana-
Haplopteris anguste-elongataLOTUS Database
Hibiscus taiwanensisPlant
Hypericum ascyronLOTUS Database
Ipomoea nilPlant
Isodon coetsaLOTUS Database
Isodon umbrosusLOTUS Database
Kigelia africanaLOTUS Database
Koyamasia calcareaLOTUS Database
Larix kaempferiLOTUS Database
Lespedeza bicolorPlant
Lonicera bournei Hemsl.LOTUS Database
Magnolia obovataLOTUS Database
Marshallia obovataLOTUS Database
Meehania urticifoliaLOTUS Database
Melissa officinalisLOTUS Database
Meum athamanticumLOTUS Database
Oenothera speciosaLOTUS Database
Perilla frutescensLOTUS Database
Persicaria perfoliataLOTUS Database
Pertya glabrescensLOTUS Database
Petasites formosanusLOTUS Database
Petasites pyrenaicusLOTUS Database
Phellodendron amurensePlant
Phellodendron chinenseLOTUS Database
Phellodendron japonicum MAXIMPlant
Plantago majorLOTUS Database
Prunus domesticaLOTUS Database
Pseudostiffita kingii-
Ricasolia virensLOTUS Database
Salvia divinorumLOTUS Database
Scorzonera hispanicaLOTUS Database
Scorzonera laciniataLOTUS Database
Sideritis lotsyiLOTUS Database
Smilax bracteataLOTUS Database
Solanum torvumLOTUS Database
Solanum tuberosumPlant
Stereospermum acuminatissimumLOTUS Database
Tanacetum odessanumPlant
Vittaria anguste-elongataPlant
Xanthium strumariumLOTUS Database
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentCoumaric acids and derivatives  
Alternative Parents
Substituents
  • Coumaric acid or derivatives
    • 

  • Cinnamic acid ester
    • 

  • Catechol
    • 

  • Styrene
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.12ALOGPS
logP1.91ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.79 m³·mol⁻¹ChemAxon
Polarizability19.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002759  
Chemspider ID600455  
KEGG Compound IDC10477  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl_caffeate  
METLIN IDNot Available
PubChem Compound689075  
PDB IDNot Available
ChEBI ID6856  
Good Scents IDrw1627011  
References
General References
  1. Gandhi GR, Ignacimuthu S, Paulraj MG, Sasikumar P: Antihyperglycemic activity and antidiabetic effect of methyl caffeate isolated from Solanum torvum Swartz. fruit in streptozotocin induced diabetic rats. Eur J Pharmacol. 2011 Nov 30;670(2-3):623-31. doi: 10.1016/j.ejphar.2011.09.159.  Epub 2011 Sep 24. [PubMed:21963451  ]