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Oleandomycin

AlkaPlorer ID: AK005631

Synonym: None

IUPAC Name: (3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione

Structure

SMILES: CO[C@H]1C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@@H](C)C[C@@]3(CO3)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C)O[C@@H](C)[C@@H]1O

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InChI: InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1

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InChIKey: RZPAKFUAFGMUPI-QESOVKLGSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Narcissus pseudonarcissus Narcissus Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces antibioticus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Artemisia iwayomogi Artemisia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Myxococcus xanthus Myxococcus Myxococcaceae Myxococcales Myxococcia Myxococcota None Bacteria
Lithospermum carolinense Lithospermum Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Drimia altissima Drimia Hyacinthaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Taxus wallichiana Taxus Taxaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Evasterias retifera Evasterias Asteriidae Forcipulatida Asteroidea Echinodermata Metazoa Eukaryota
Sideritis glacialis Sideritis Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aconitum umbrosum Aconitum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Helenium amarum Helenium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Scutellaria viscidula Scutellaria Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Uperoleia rugosa Uperoleia Myobatrachidae Anura Amphibia Chordata Metazoa Eukaryota
Bolboschoenus maritimus Bolboschoenus Cyperaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ligularia lankongensis Ligularia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Allium ampeloprasum Allium Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Maytenus disticha Maytenus Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Conyza pallidiflora Conyza Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Senecio retrorsus Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lonicera nitida Lonicera Caprifoliaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 687.8680000000003

TPSA？: 165.98

MolLogP？: 1.908500000000004

Number of H-Donors: 3

Number of H-Acceptors: 13

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Burkholderia pseudomallei Burkholderia pseudomallei MIC 0.25 ug.mL-1 10.1128/aac.01033-06
Burkholderia pseudomallei Burkholderia pseudomallei MIC 0.5 ug.mL-1 10.1128/aac.01033-06
Burkholderia pseudomallei Burkholderia pseudomallei MIC 64.0 ug.mL-1 10.1128/aac.01033-06
Burkholderia pseudomallei Burkholderia pseudomallei MIC 128.0 ug.mL-1 10.1128/aac.01033-06
Burkholderia pseudomallei Burkholderia pseudomallei MIC 256.0 ug.mL-1 10.1128/aac.01033-06
Burkholderia pseudomallei Burkholderia pseudomallei MIC 512.0 ug.mL-1 10.1128/aac.01033-06
Burkholderia pseudomallei Burkholderia pseudomallei MIC 1024.0 ug.mL-1 10.1128/aac.01033-06
Burkholderia pseudomallei Burkholderia pseudomallei MIC 2000.0 ug.mL-1 10.1128/aac.01033-06
Escherichia coli Escherichia coli MIC 64.0 ug.mL-1 10.1128/aac.01126-09
Escherichia coli Escherichia coli MIC 128.0 ug.mL-1 10.1128/aac.01048-06
Escherichia coli Escherichia coli MIC 256.0 ug.mL-1 10.1128/aac.01048-06
Escherichia coli Escherichia coli MIC 256.0 ug.mL-1 10.1128/aac.01126-09
Escherichia coli Escherichia coli MIC 512.0 ug.mL-1 10.1128/aac.01048-06
Escherichia coli Escherichia coli MIC 1024.0 ug.mL-1 10.1128/aac.01126-09
Homo sapiens Homo sapiens Vdss 0.77 L.kg-1 10.1021/jm9004658
Homo sapiens Proteinase-activated receptor 2 Inhibition nan % 10.1128/aac.00140-07
Mus musculus Mus musculus PD50 150.0 mg kg-1 10.1021/jm960436i
Pasteurella multocida Pasteurella multocida MIC 6.25 ug.mL-1 10.1021/jm960436i
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Streptomyces antibioticus Oleandomycin glycosyltransferase Activity 13.0 nmol/min 10.1038/nchembio.2007.28
Streptomyces antibioticus Oleandomycin glycosyltransferase Activity 70.0 nmol/min 10.1038/nchembio.2007.28
Streptomyces antibioticus Oleandomycin glycosyltransferase Activity 200.0 nmol/min 10.1038/nchembio.2007.28
Streptomyces antibioticus Oleandomycin glycosyltransferase Activity 700.0 nmol/min 10.1038/nchembio.2007.28
Streptomyces antibioticus Oleandomycin glycosyltransferase Activity 1487.0 nmol/min 10.1038/nchembio.2007.28
None ADMET Log K 0.01 None 10.1021/jm960436i
None ADMET pCF 0.015 None 10.1021/jm960436i
None ADMET pNF 1.455 None 10.1021/jm960436i
None No relevant target CLogP 0.0 None 10.1021/jm960436i
None No relevant target CLogP 0.596 None 10.1021/jm960436i
None No relevant target CLogP 1.69 None 10.1021/jm960436i
None No relevant target LogD 0.43 None 10.1021/jm960436i
None No relevant target pKa 8.84 None 10.1007/s11095-013-1232-z
None No relevant target pKa1 8.84 None 10.1021/jm960436i

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011314 CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O)[C@H]2C)O[C@@H](C)[C@@H]1O.Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)O2)c(=O)[nH]c1=O>>CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O RXN-12803
AKRT011315 CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3OP(=O)(O)O)[C@H]2C)O[C@@H](C)[C@@H]1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O None
AKRT011316 CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O RXN-12919
AKRT011317 CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O MNXR176531
AKRT011318 CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O>>CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3OP(=O)(O)O)[C@H]2C)O[C@@H](C)[C@@H]1O MACROLIDE-2-KINASE-RXN
AKRT011319 CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O>>CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O RXN-12920
AKRT011320 CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3OP(=O)(O)O)[C@H]2C)O[C@@H](C)[C@@H]1O>>CO[C@H]1C[C@H](O[C@@H]2[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]3(CO3)C[C@H](C)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]2C)O[C@@H](C)[C@@H]1O MACROLIDE-2-KINASE-RXN