Summary

IMPPAT Phytochemical identifier: IMPHY005668

Phytochemical name: methyl (2R)-8-methyl-3-[(E)-3-phenylprop-2-enoyl]oxy-8-azabicyclo[3.2.1]octane-2-carboxylate

Synonymous chemical names:
cinnamoylcocaine, cinnamylcocaine

External chemical identifiers:
CID:20054874, SureChEMBL:SCHEMBL917539

---

Chemical structure information

SMILES:
COC(=O)[C@H]1C(OC(=O)/C=C/c2ccccc2)CC2N(C1CC2)C

InChI:
InChI=1S/C19H23NO4/c1-20-14-9-10-15(20)18(19(22)23-2)16(12-14)24-17(21)11-8-13-6-4-3-5-7-13/h3-8,11,14-16,18H,9-10,12H2,1-2H3/b11-8+/t14?,15?,16?,18-/m1/s1

InChIKey:
MQIXMJWNEKUAOZ-GKMMPQBVSA-N

DeepSMILES:
COC=O)[C@H]COC=O)/C=C/cccccc6))))))))))CCNC6CC5)))C

Functional groups:
CN(C)C, COC(C)=O, c/C=C/C(=O)OC

---

Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(C=Cc1ccccc1)OC1CC2CCC(C1)N2

Scaffold Graph/Node level:
OC(CCC1CCCCC1)OC1CC2CCC(C1)N2

Scaffold Graph level:
CC(CCC1CCCCC1)CC1CC2CCC(C2)C1

---

Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Phenylpropanoids and polyketides

ClassyFire Class: Cinnamic acids and derivatives

ClassyFire Subclass: Cinnamic acid esters

NP Classifier Biosynthetic pathway: Alkaloids

NP Classifier Superclass: Ornithine alkaloids

NP Classifier Class: Tropane alkaloids

NP-Likeness score: 1.138

---

Chemical structure download