cis-Cinnamoylcocaine

Details

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Internal ID 1fcad5d0-348d-42c8-aa53-c52a09c25b6a
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
IUPAC Name methyl (1R,2R,3S,5S)-8-methyl-3-[(Z)-3-phenylprop-2-enoyl]oxy-8-azabicyclo[3.2.1]octane-2-carboxylate
SMILES (Canonical) CN1C2CCC1C(C(C2)OC(=O)C=CC3=CC=CC=C3)C(=O)OC
SMILES (Isomeric) CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)/C=C\C3=CC=CC=C3)C(=O)OC
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+/m0/s1
InChI Key MQIXMJWNEKUAOZ-ZFYRMRLISA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C19H23NO4
Molecular Weight 329.40 g/mol
Exact Mass 329.16270821 g/mol
Topological Polar Surface Area (TPSA) 55.80 Ų
XlogP 2.70

Synonyms

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Cinnamoylcocaine, (Z)-
R3M4L88DXV
50763-21-8
methyl (1R,2R,3S,5S)-8-methyl-3-[(Z)-3-phenylprop-2-enoyl]oxy-8-azabicyclo[3.2.1]octane-2-carboxylate
8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 8-methyl-3-(((2Z)-1-oxo-3-phenyl-2-propen-1-yl)oxy)-, methyl ester, (1R,2R,3S,5S)-
8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 8-methyl-3-(((2Z)-1-oxo-3-phenyl-2-propenyl)oxy)-, methyl ester, (1R,2R,3S,5S)-
(Z)-cinnamoylcocaine
UNII-R3M4L88DXV
Q27287749
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 8-METHYL-3-((1-OXO-3-PHENYL-2-PROPENYL)OXY)-, METHYL ESTER, (1R-(1.ALPHA.,2.ALPHA.,3.ALPHA.(Z),5.ALPHA.))-
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of cis-Cinnamoylcocaine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
No predicted properties yet!

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.87% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.81% 95.56%
CHEMBL221 P23219 Cyclooxygenase-1 94.11% 90.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.95% 96.00%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 93.40% 94.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.56% 86.33%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 92.12% 94.08%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.94% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 89.34% 83.82%
CHEMBL2581 P07339 Cathepsin D 89.09% 98.95%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 88.65% 97.21%
CHEMBL5028 O14672 ADAM10 85.01% 97.50%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 82.98% 94.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.85% 97.09%
CHEMBL340 P08684 Cytochrome P450 3A4 80.84% 91.19%
CHEMBL4208 P20618 Proteasome component C5 80.07% 90.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Erythroxylum coca
Erythroxylum novogranatense

Cross-Links

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PubChem 12798013
LOTUS LTS0213762
wikiData Q27287749