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Eburnamonine

AlkaPlorer ID: AK004711

Synonym: '', 'Eburnamonine', '(-)-cis-Eburnamonine', 'eburnamonine monohydrochloride', 'eburnamonine phosphate', '(+)-Eburnamonine', '(+)-cis-Eburnamonine', '(-)-Eburnamonine; Vinburnine; Vincamone', '(+)-Vincamone', '(+)-cis-Vincamone', 'Vinburnine', '(-)-Vincamone', 'cervoxan', 'd-Eburnamonine', 'l-Eburnamonine', 'vincamone'

IUPAC Name: (15R,19R)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-one

Structure

SMILES: CC[C@]12CCCN3CCC4=C([C@H]31)N(C(=O)C2)C1=CC=CC=C41

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InChI: InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m0/s1

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InChIKey: WYJAPUKIYAZSEM-RBUKOAKNSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Vepris uguenensis Vepris Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 294.398

TPSA？: 25.24

MolLogP？: 3.774600000000003

Number of H-Donors: 0

Number of H-Acceptors: 3

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Enterococcus faecalis Enterococcus faecalis MIC 2000.0 nM 10.1021/acs.jnatprod.6b00011
Escherichia coli Escherichia coli MIC 85000.0 nM 10.1021/acs.jnatprod.6b00011
Homo sapiens Cytochrome P450 1A2 AC50 10000.0 nM None
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 10000.0 nM None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 Potency 7943.3 nM None
Homo sapiens Cytochrome P450 2C19 Potency 10000.0 nM None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 Potency 25118.9 nM None
Homo sapiens Cytochrome P450 2D6 AC50 19.95 nM None
Homo sapiens Cytochrome P450 2D6 AC50 251.19 nM None
Homo sapiens Cytochrome P450 2D6 Potency 20.0 nM None
Homo sapiens Cytochrome P450 2D6 Potency 63.1 nM None
Homo sapiens Cytochrome P450 2D6 Potency 251.2 nM None
Homo sapiens Cytochrome P450 3A4 AC50 3981.07 nM None
Homo sapiens Cytochrome P450 3A4 AC50 6309.57 nM None
Homo sapiens Cytochrome P450 3A4 Potency 3981.1 nM None
Homo sapiens Cytochrome P450 3A4 Potency 6309.6 nM None
Homo sapiens Geminin Potency 10137.4 nM None
Homo sapiens Geminin Potency 11374.3 nM None
Homo sapiens Pregnane X receptor Activity nan None 10.1124/dmd.110.035105
Homo sapiens Pregnane X receptor EC50 12600.0 nM 10.1124/dmd.110.035105
Homo sapiens Pregnane X receptor EC50 14100.0 nM 10.1124/dmd.110.035105
Homo sapiens Pregnane X receptor Efficacy 49.9 % 10.1124/dmd.110.035105
Homo sapiens Pregnane X receptor Efficacy 60.3 % 10.1124/dmd.110.035105
Homo sapiens Prelamin-A/C Potency 14125.4 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 31622.8 nM None
Klebsiella pneumoniae Klebsiella pneumoniae MIC 150000.0 nM 10.1021/acs.jnatprod.6b00011
Plasmodium falciparum Plasmodium falciparum Potency 6424.1 nM None
Plasmodium falciparum Plasmodium falciparum Potency 7208.0 nM None
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 5000.0 nM 10.1021/acs.jnatprod.6b00011
Rattus norvegicus Nuclear receptor subfamily 1 group I member 2 EC50 14100.0 nM 10.1124/dmd.110.035105
Rattus norvegicus Nuclear receptor subfamily 1 group I member 2 Efficacy 144.3 % 10.1124/dmd.110.035105
Staphylococcus aureus Staphylococcus aureus MIC 150000.0 nM 10.1021/acs.jnatprod.6b00011

Metabolism Information