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Vittatine

AlkaPlorer ID: AK000399

Synonym: None

IUPAC Name: (1R,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-15-ol

Structure

SMILES: O[C@@H]1C=C[C@]23CCN(CC4=CC5=C(C=C42)OCO5)[C@H]3C1

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InChI: InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15+,16+/m1/s1

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InChIKey: RPAORVSEYNOMBR-RLCCDNCMSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Crinum asiaticum Crinum Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Elaeocarpus sphaericus Elaeocarpus Elaeocarpaceae Oxalidales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crotalaria crispata Crotalaria Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Angelica hirsutiflora Angelica Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lycoris radiata Lycoris Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Datura wrightii Datura Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Salvia keerlii Salvia Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Glycyrrhiza eurycarpa Glycyrrhiza Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cinchona officinalis Cinchona Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Atriplex parvifolia Atriplex Chenopodiaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Anthoceros punctatus Anthoceros Anthocerotaceae Anthocerotales Anthocerotopsida Streptophyta Viridiplantae Eukaryota
Hesperocyparis arizonica Hesperocyparis Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Amaryllis belladonna Amaryllis Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lupinus holosericeus Lupinus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crinum yemense Crinum Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Searsia leptodictya Searsia Anacardiaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Helichrysum asperum Helichrysum Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Artemisia juncea Artemisia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Murraya paniculata Murraya Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Viburnum lantana Viburnum Adoxaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 271.31600000000003

TPSA？: 41.93000000000001

MolLogP？: 1.5618

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli Escherichia coli IZ 22.0 mm 10.1016/j.bmcl.2017.09.052
Homo sapiens DNA topoisomerase I Inhibition nan % 10.1016/j.bmcl.2011.09.097
Homo sapiens DNA topoisomerase II alpha Inhibition nan % 10.1016/j.bmcl.2011.09.097
Plasmodium falciparum Plasmodium falciparum IC50 7300.0 nM 10.1016/j.bmc.2012.07.036
Staphylococcus aureus Staphylococcus aureus IZ 19.0 mm 10.1016/j.bmcl.2017.09.052
None ADMET Activity 102.7 % 10.1021/np030529k
None ADMET Activity 105.7 % 10.1021/np030529k
None ADMET Activity 106.7 % 10.1021/np030529k
None ADMET Activity 108.0 % 10.1021/np030529k
None ADMET Activity 108.7 % 10.1021/np030529k
None Macrophage Inhibition -12.5 % 10.1021/np030529k
None Macrophage Inhibition -0.2 % 10.1021/np030529k
None Macrophage Inhibition 7.1 % 10.1021/np030529k
None Macrophage Inhibition 13.1 % 10.1021/np030529k
None Macrophage Inhibition 42.4 % 10.1021/np030529k
None Nucleic Acid Activity nan None 10.1016/j.bmcl.2011.09.097

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011644 COc1cc2c(cc1O)CN1CC[C@@]23C=C[C@@H](O)C[C@H]13>>O[C@@H]1C=C[C@]23CCN(Cc4cc5c(cc42)OCO5)[C@H]3C1 RXN-18136
AKRT024858 O[C@@H]1C=C[C@]23CCN(Cc4cc5c(cc42)OCO5)[C@H]3C1>>O[C@@H]1C=C[C@@]23c4cc5c(cc4CN(C[C@H]2O)[C@H]3C1)OCO5 RXN-18140