:Clovamide

{{Chembox

| Name =

| ImageFile1 = Cis-Clovamide Structure.svg

| ImageSize1 = 200px

| ImageCaption1 = cis-Clovamide

| ImageFile2 = Clovamide.svg

| ImageSize2 = 200px

| ImageCaption2 = trans-Clovamide

| IUPACName = (2S)-3-(3,4-Dihydroxyphenyl)-2-[[(Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]propanoic acid

| OtherNames = N-Caffeoyl-L-DOPA

| SystematicName =

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 53755-03-6

| CASNo_Comment = (cis)

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo1 = 53755-02-5

| CASNo1_Comment = (trans)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = WZC65G68KW

| UNII_Comment = (cis)

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = 973626KV9L

| UNII1_Comment = (trans)

| PubChem = 6443790

| ChemSpiderID = 4947752

| SMILES = c1cc(c(cc1C[C@@H](C(=O)O)NC(=O)/C=C\c2ccc(c(c2)O)O)O)O

| InChI = 1/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-/t12-/m0/s1

| InChIKey = GPZFXSWMDFBRGS-RYBZSIHZBZ

| StdInChI = 1S/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3-/t12-/m0/s1

| StdInChIKey = GPZFXSWMDFBRGS-RYBZSIHZSA-N

}}

| Section2 = {{Chembox Properties

| C=18|H=17|N=1|O=7

}}

| Section3 =

| Section4 =

| Section5 =

| Section6 =

}}

Clovamide is a chemical compound found in cacao.{{cite journal | doi = 10.1021/jf970575o| title = Antioxidative Polyphenols Isolated from Theobromacacao| year = 1998| last1 = Sanbongi| first1 = Chiaki| last2 = Osakabe| first2 = Naomi| last3 = Natsume| first3 = Midori| last4 = Takizawa| first4 = Toshio| last5 = Gomi| first5 = Shuichi| last6 = Osawa| first6 = Toshihiko| journal = Journal of Agricultural and Food Chemistry| volume = 46| issue = 2| pages = 454–457| pmid = 10554262}}{{cite journal | doi = 10.1016/j.foodchem.2007.07.009| title = Roasting impact on the contents of clovamide (N-caffeoyl-L-DOPA) and the antioxidant activity of cocoa beans (Theobroma cacao L.)| year = 2008| last1 = Arlorio| first1 = Marco| last2 = Locatelli| first2 = Monica| last3 = Travaglia| first3 = Fabiano| last4 = Coïsson| first4 = Jean-Daniel| last5 = Grosso| first5 = Erika Del| last6 = Minassi| first6 = Alberto| last7 = Appendino| first7 = Giovanni| last8 = Martelli| first8 = Aldo| journal = Food Chemistry| volume = 106| issue = 3| pages = 967–975}} It has only been found in small amounts.{{cite book | last1=Caballero | first1=B. | last2=Finglas | first2=P. | last3=Toldrรก | first3=F. | title=Encyclopedia of Food and Health | publisher=Elsevier Science | year=2015 | isbn=978-0-12-384953-3 | url=https://books.google.com/books?id=O-t9BAAAQBAJ&pg=RA1-PA189 | page=189}} It is also found in Trifolium pratense (red clover).Induction of clovamide by jasmonic acid in red clover. Tebayashi S, Ishihara A, Tsuda M and Iwamura H, Phytochemistry, 2000 Jun, 54(4), pages 387-392, {{PMID|10897479}}

Clovamide can exist as either the cis- or trans- isomer.

In isolated neuroblastoma cells, clovamide has in vitro neuroprotective effects.{{Cite journal |pmc = 2737666|year = 2009|last1 = Fallarini|first1 = S.|title = Clovamide and rosmarinic acid induce neuroprotective effects in in vitro models of neuronal death|journal = British Journal of Pharmacology|volume = 157|issue = 6|pages = 1072–1084|last2 = Miglio|first2 = G.|last3 = Paoletti|first3 = T.|last4 = Minassi|first4 = A.|last5 = Amoruso|first5 = A.|last6 = Bardelli|first6 = C.|last7 = Brunelleschi|first7 = S.|last8 = Lombardi|first8 = G.|pmid = 19466982|doi = 10.1111/j.1476-5381.2009.00213.x}}