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AROMOLINE

AlkaPlorer ID: AK008371

Synonym: '', '(+)-12-O-Demethyllimacusine', 'Macolidine', 'Thalicrine', 'Aromoline', '(+)-Candicusine', '(+)-Aromoline'

IUPAC Name: (1R,14S)-20,25-dimethoxy-15,30-dimethyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-3(36),4,6,9(35),10,12(34),18,20,22(33),24,26,31-dodecaene-6,21-diol

Structure

SMILES: COC1=C2C=C3C(=C1)CCN(C)[C@@H]3CC1=CC=C(O)C(=C1)OC1=CC=C(C=C1)C[C@H]1C3=C(C=C(OC)C(O)=C3O2)CCN1C

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InChI: InChI=1S/C36H38N2O6/c1-37-13-11-23-18-31(41-3)32-20-26(23)27(37)16-22-7-10-29(39)30(17-22)43-25-8-5-21(6-9-25)15-28-34-24(12-14-38(28)2)19-33(42-4)35(40)36(34)44-32/h5-10,17-20,27-28,39-40H,11-16H2,1-4H3/t27-,28+/m1/s1

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InChIKey: LFFQVHXIFJLJSP-IZLXSDGUSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Rothmannia globosa Rothmannia Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Koenigia coriaria Koenigia Polygonaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alnus formosana Alnus Betulaceae Fagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Morus alba Morus Moraceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Eleutherococcus divaricatus Eleutherococcus Araliaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Choisya ternata Choisya Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Conyza aegyptiaca Conyza Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Pilosocereus chrysacanthus Pilosocereus Cactaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cryptostegia madagascariensis Cryptostegia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Trigonella corniculata Trigonella Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dalbergia sissoides Dalbergia Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dunaliella salina Dunaliella Dunaliellaceae Chlamydomonadales Chlorophyceae Chlorophyta Viridiplantae Eukaryota
Pestalotiopsis disseminata Pestalotiopsis Sporocadaceae Xylariales Sordariomycetes Ascomycota Fungi Eukaryota
Lampropeltis getula Lampropeltis Colubridae Squamata Lepidosauria Chordata Metazoa Eukaryota
Alstonia venenata Alstonia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Copris tripartitus Copris Scarabaeidae Coleoptera Insecta Arthropoda Metazoa Eukaryota
Coleonema pulchellum Coleonema Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tamarix chinensis Tamarix Tamaricaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Pycnarrhena longifolia Pycnarrhena Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Panax quinquefolius Panax Araliaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Berberis vulgaris Berberis Berberidaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hymenoxys richardsonii Hymenoxys Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cussonia paniculata Cussonia Araliaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 594.7080000000001

TPSA？: 83.86000000000001

MolLogP？: 6.556400000000008

Number of H-Donors: 2

Number of H-Acceptors: 8

RingCount: 8

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens 786-0 GI50 6516.28 nM None
Homo sapiens A498 GI50 16710.91 nM None
Homo sapiens A549 GI50 15170.5 nM None
Homo sapiens Acetylcholinesterase IC50 100000.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens ACHN GI50 19364.22 nM None
Homo sapiens BT-549 GI50 12852.87 nM None
Homo sapiens Butyrylcholinesterase IC50 800.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens Butyrylcholinesterase Ki 6410.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens Butyrylcholinesterase Ki 39700.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens CAKI-1 GI50 25941.79 nM None
Homo sapiens CCRF-CEM GI50 10351.42 nM None
Homo sapiens COLO 205 GI50 13803.84 nM None
Homo sapiens DU-145 GI50 15066.07 nM None
Homo sapiens EKVX GI50 16710.91 nM None
Homo sapiens Glycogen synthase kinase-3 beta Inhibition 10.0 % 10.1021/acs.jnatprod.8b00592
Homo sapiens HCC 2998 GI50 7046.93 nM None
Homo sapiens HCT-116 GI50 5767.66 nM None
Homo sapiens HCT-15 GI50 9289.66 nM None
Homo sapiens HL-60 GI50 6683.44 nM None
Homo sapiens HOP-62 GI50 16368.17 nM None
Homo sapiens HOP-92 GI50 6637.43 nM None
Homo sapiens Hs-578T GI50 20044.72 nM None
Homo sapiens HT-29 GI50 3837.07 nM None
Homo sapiens IGROV-1 GI50 13835.66 nM None
Homo sapiens K562 GI50 2564.48 nM None
Homo sapiens KB ED50 14800.0 nM 10.1021/np980144f
Homo sapiens KM12 GI50 9015.71 nM None
Homo sapiens LOX IMVI GI50 4943.11 nM None
Homo sapiens M14 GI50 2249.05 nM None
Homo sapiens Malme-3M GI50 17298.16 nM None
Homo sapiens MCF7 GI50 13304.54 nM None
Homo sapiens MDA-MB-231 GI50 10256.52 nM None
Homo sapiens MDA-MB-435 GI50 10739.89 nM None
Homo sapiens MDA-N GI50 10715.19 nM None
Homo sapiens MOLT-4 GI50 8413.95 nM None
Homo sapiens NCI/ADR-RES GI50 24490.63 nM None
Homo sapiens NCI-H226 GI50 29376.5 nM None
Homo sapiens NCI-H23 GI50 22387.21 nM None
Homo sapiens NCI-H322M GI50 16865.53 nM None
Homo sapiens NCI-H460 GI50 8994.98 nM None
Homo sapiens NCI-H522 GI50 11040.79 nM None
Homo sapiens OVCAR-3 GI50 10185.91 nM None
Homo sapiens OVCAR-4 GI50 16904.41 nM None
Homo sapiens OVCAR-5 GI50 23604.78 nM None
Homo sapiens OVCAR-8 GI50 14927.94 nM None
Homo sapiens PC-3 GI50 8511.38 nM None
Homo sapiens Prolyl endopeptidase IC50 189000.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens RPMI-8226 GI50 5333.35 nM None
Homo sapiens RXF 393 GI50 3630.78 nM None
Homo sapiens SF-268 GI50 14421.15 nM None
Homo sapiens SF-295 GI50 12416.52 nM None
Homo sapiens SF-539 GI50 3228.49 nM None
Homo sapiens SK-MEL-2 GI50 12274.39 nM None
Homo sapiens SK-MEL-28 GI50 19186.69 nM None
Homo sapiens SK-MEL-5 GI50 7328.25 nM None
Homo sapiens SK-OV-3 GI50 25351.29 nM None
Homo sapiens SN12C GI50 4168.69 nM None
Homo sapiens SNB-19 GI50 20892.96 nM None
Homo sapiens SNB-75 GI50 18793.17 nM None
Homo sapiens SR GI50 1625.55 nM None
Homo sapiens SW-620 GI50 16519.62 nM None
Homo sapiens T47D GI50 17906.06 nM None
Homo sapiens TK-10 GI50 13551.89 nM None
Homo sapiens U-251 GI50 9484.18 nM None
Homo sapiens UACC-257 GI50 14962.36 nM None
Homo sapiens UACC-62 GI50 17418.07 nM None
Homo sapiens UO-31 GI50 12647.36 nM None
Plasmodium falciparum Plasmodium falciparum IC50 446.0 nM 10.1021/np980144f
Plasmodium falciparum Plasmodium falciparum IC50 1400.0 nM 10.1021/np980144f
None No relevant target permeability 1.8 ucm/s 10.1021/acs.jnatprod.8b00592
None Unchecked Ratio IC50 0.008 None 10.1021/acs.jnatprod.8b00592
None Unchecked Selectivity Index 11.0 None 10.1021/np980144f
None Unchecked Selectivity Index 33.0 None 10.1021/np980144f

Metabolism Information