:Lombricine

{{Chembox

| ImageFile = Lombricine.svg

| ImageSize = 200px

| IUPACName = O-[{2-[(Diaminomethylene)amino]ethoxy}(hydroxy)phosphoryl]-D-serine

| OtherNames = D-Lombricine

|Section1={{Chembox Identifiers

| CASNo = 79342-60-2

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

| UNII = YMK242B63W

| PubChem = 439556

| ChemSpiderID = 388647

| ChEBI = 32969

| SMILES = O=C(O)[C@H](N)COP(=O)(OCC/N=C(\N)N)O

| InChI = 1/C6H15N4O6P/c7-4(5(11)12)3-16-17(13,14)15-2-1-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H,13,14)(H4,8,9,10)/t4-/m1/s1

| InChIKey = GSDBGCKBBJVPNC-SCSAIBSYBR

| StdInChI = 1S/C6H15N4O6P/c7-4(5(11)12)3-16-17(13,14)15-2-1-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H,13,14)(H4,8,9,10)/t4-/m1/s1

| StdInChIKey = GSDBGCKBBJVPNC-SCSAIBSYSA-N

}}

|Section2={{Chembox Properties

| C=6 | H=15 | N=4 | O=6 | P=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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Lombricine is a phosphagen that is unique to earthworms. Structurally, it is a phosphodiester of 2-guanidinoethanol and D-serine (not the usual L-serine),{{cite journal | pmid = 13743749 | year = 1960 | last1 = Rossiter | first1 = RJ | last2 = Gaffney | first2 = TJ | last3 = Rosenberg | first3 = H | last4 = Ennor | first4 = AH | title = The formation in vivo of lombricine in the earthworm (Megascolides cameroni) | volume = 76 | pages = 603–10 | pmc = 1204840 | journal = The Biochemical Journal | issue = 3 | doi=10.1042/bj0760603}} which is then further phosphorylated by lombricine kinase to phospholombricine.