Molecule

Akuammicine

AlkaPlorer ID: AK004496

Synonym: None

IUPAC Name: methyl (1R,11S,12E,17S)-12-ethylidene-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carboxylate

Structure

SMILES: C/C=C1/CN2CC[C@]34C(=C(C(=O)OC)[C@H]1C[C@H]23)NC1=CC=CC=C14

InChI: InChI=1S/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)17(19(23)24-2)13(12)10-16(20)22/h3-7,13,16,21H,8-11H2,1-2H3/b12-3-/t13-,16-,20+/m0/s1

InChIKey: AGZMFTKKLPHOMT-DUJTVWLASA-N

Reference

Leuconicines A−G and (−)-Eburnamaline, Biologically Active Strychnan and Eburnan Alkaloids from <i>Leuconotis</i>

PubChem CID: 10314057

CAS: 639-43-0

LOTUS: LTS0143331

SuperNatural Ⅲ: SN0005387-03

NPASS: NPC193410

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Uncaria rhynchophylla	Uncaria	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Catharanthus trichophyllus	Catharanthus	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Catharanthus roseus	Catharanthus	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 322.408

TPSA？: 41.57

MolLogP？: 2.831100000000001

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Electrophorus electricus	Acetylcholinesterase	IC50	221000.0	nM	10.1021/np960070c
Homo sapiens	A549	IC50	15000.0	nM	10.1021/np0502701
Homo sapiens	Delta opioid receptor	Inhibition	nan	%	10.1021/acs.jnatprod.0c01036
Homo sapiens	Delta opioid receptor	Ki	23200.0	nM	10.1021/acs.jnatprod.0c01036
Homo sapiens	Delta opioid receptor	Ki	25118.86	nM	10.1021/acs.jnatprod.0c01036
Homo sapiens	Dopamine D5 receptor	Inhibition	nan	%	10.1021/acs.jnatprod.0c01036
Homo sapiens	Dopamine D5 receptor	Ki	10000.0	nM	10.1021/acs.jnatprod.0c01036
Homo sapiens	Histamine H3 receptor	Inhibition	60.0	%	10.1021/acs.jnatprod.0c01036
Homo sapiens	Kappa opioid receptor	Activity	50.0	%	10.1021/acs.jnatprod.0c01036
Homo sapiens	Kappa opioid receptor	EC50	39810.72	nM	10.1021/acs.jnatprod.0c01036
Homo sapiens	Kappa opioid receptor	Inhibition	nan	%	10.1021/acs.jnatprod.0c01036
Homo sapiens	Kappa opioid receptor	Ki	79.43	nM	10.1021/acs.jnatprod.0c01036
Homo sapiens	Kappa opioid receptor	Ki	89.0	nM	10.1021/acs.jnatprod.0c01036
Homo sapiens	Mu opioid receptor	Inhibition	nan	%	10.1021/acs.jnatprod.0c01036
Homo sapiens	Mu opioid receptor	Ki	3162.28	nM	10.1021/acs.jnatprod.0c01036
Homo sapiens	Mu opioid receptor	Ki	3310.0	nM	10.1021/acs.jnatprod.0c01036
Homo sapiens	Serotonin transporter	Inhibition	60.0	%	10.1021/acs.jnatprod.0c01036
Mus musculus	Delta opioid receptor	Activity	60.0	%	10.1021/acs.jnatprod.0c01036
Mus musculus	Delta opioid receptor	IC50	12400.0	nM	10.1021/acs.jnatprod.0c01036
Mus musculus	Delta opioid receptor	IC50	12589.25	nM	10.1021/acs.jnatprod.0c01036
Mus musculus	Kappa opioid receptor	Activity	84.0	%	10.1021/acs.jnatprod.0c01036
Mus musculus	Kappa opioid receptor	IC50	240.0	nM	10.1021/acs.jnatprod.0c01036
Mus musculus	Kappa opioid receptor	IC50	251.19	nM	10.1021/acs.jnatprod.0c01036
Mus musculus	Mu opioid receptor	Activity	45.0	%	10.1021/acs.jnatprod.0c01036
Mus musculus	Mu opioid receptor	IC50	7943.28	nM	10.1021/acs.jnatprod.0c01036
Mus musculus	Mu opioid receptor	IC50	8240.0	nM	10.1021/acs.jnatprod.0c01036
Mus musculus	P388	ED50	1.7	ug ml-1	10.1021/np50015a017
None	NON-PROTEIN TARGET	ED50	2.4	ug ml-1	10.1021/np50015a017
None	NON-PROTEIN TARGET	IC50	12.29	ug.mL-1	10.1021/np100552b
None	NON-PROTEIN TARGET	IC50	25.0	ug.mL-1	10.1021/np100552b

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT001514	C/C=C1/CN2CC[C@@]34C(=Nc5ccccc53)[C@](C(=O)OC)(C(O)O)[C@H]1C[C@H]24>>C/C=C1/CN2CC[C@]34C(=C(C(=O)OC)[C@H]1C[C@H]23)Nc1ccccc14	RXN-19980
AKRT001520	C/C=C1/CN2CCc3c([nH]c4ccccc34)[C@@H]2C[C@@H]1/C(=C\O)C(=O)OC>>C/C=C1/CN2CC[C@]34C(=C(C(=O)OC)[C@H]1C[C@H]23)Nc1ccccc14	58520
AKRT001549	C/C=C1/C[N+]2=CC[C@@H]1[C@](C=O)(C(=O)OC)c1[nH]c3ccccc3c1CC2>>C/C=C1/CN2CC[C@]34C(=C(C(=O)OC)[C@H]1C[C@H]23)Nc1ccccc14	58532