Octopine

Not to be confused with octopamine.

Octopine

Stereo, skeletal formula of octopine ((2S)-2-{[(1R)-1-carboxyethyl]amino})
Names
IUPAC name 2-[[1-Carboxyethyl]amino]-5-(diaminomethylideneamino)pentanoic acid
Identifiers
CAS Number	34522-32-2 (2S)-2-{[(1R)-1-Carboxyethyl]amino} N
3DMet	B04929
ChEBI	CHEBI:15805 Y
ChemSpider	414 N 389221 (2S)-2-Amino N 97253 (2S)-2-{[(1R)-1-Carboxyethyl]amino} N
Jmol 3D model	Interactive image Interactive image
KEGG	C04137 N
MeSH	octopine
PubChem	427 440237 (2S)-2-Amino 12313676 (2S)-2-{[(1S)-1-Carboxyethyl]amino} 108172 (2S)-2-{[(1R)-1-Carboxyethyl]amino}
InChI InChI=1S/C9H18N4O4/c1-5(7(14)15)13-6(8(16)17)3-2-4-12-9(10)11/h5-6,13H,2-4H2,1H3,(H,14,15)(H,16,17)(H4,10,11,12) N Key: IMXSCCDUAFEIOE-UHFFFAOYSA-N N
SMILES CC(NC(CCC[nH]:c(:[nH]):[nH2])c(:[o]):[oH])c(:[o]):[oH] CC(NC(CCCNC(N)=N)C(O)=O)C(O)=O
Properties
Chemical formula	C9H18N4O4
Molar mass	246.27 g·mol−1
Related compounds
Related alkanoic acids	Daminozide Nopaline
Related compounds	Bis-tris propane Pantetheine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Octopine is a derivative of the amino acids arginine and alanine. It was the first member of the class of chemical compounds known as opines to be discovered. Octopine gets its name from Octopus octopodia from which it was first isolated in 1927.

Octopine has been isolated from the muscle tissue of invertebrates such as octopus, Pecten maximus and Sipunculus nudus where it functions as an analog of lactic acid. It is also produced by Agrobacterium and causes crown gall tumor growth in plants.

Octopine is formed by reductive condensation of pyruvic acid and arginine through the action of the NADH-dependent enzyme octopine dehydrogenase (ODH). The reaction is reversible so that pyruvic acid and arginine can be regenerated.

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