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jadomycin B

AlkaPlorer ID: AK010414

Synonym: '', 'jadomycin B', 'Jadomycin B'

IUPAC Name: (3S,6S)-3-[(2S)-butan-2-yl]-19-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-11-hydroxy-9-methyl-5-oxa-2-azapentacyclo[11.8.0.02,6.07,12.015,20]henicosa-1(13),7(12),8,10,15(20),16,18-heptaene-4,14,21-trione

Structure

SMILES: CC[C@H](C)[C@H]1C(=O)O[C@H]2C3=CC(C)=CC(O)=C3C3=C(C(=O)C4=C(O[C@H]5C[C@@H](O)[C@@H](O)[C@H](C)O5)C=CC=C4C3=O)N12

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InChI: InChI=1S/C30H31NO9/c1-5-13(3)24-30(37)40-29-16-9-12(2)10-17(32)21(16)23-25(31(24)29)28(36)22-15(27(23)35)7-6-8-19(22)39-20-11-18(33)26(34)14(4)38-20/h6-10,13-14,18,20,24,26,29,32-34H,5,11H2,1-4H3/t13-,14-,18+,20-,24-,26-,29-/m0/s1

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InChIKey: BSBSCJRAEMDCHC-FTERDKBNSA-N

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Properties Information

Molecule Weight: 549.5760000000002

TPSA？: 142.83

MolLogP？: 3.012120000000001

Number of H-Donors: 3

Number of H-Acceptors: 10

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis Bacillus subtilis MIC 4.0 ug.mL-1 10.1128/aac.00801-08
Enterococcus faecalis Enterococcus faecalis MIC 32.0 ug.mL-1 10.1128/aac.00801-08
Homo sapiens MDA-MB-435 EC50 6890.0 nM 10.1016/j.bmc.2011.04.043
Homo sapiens T47D EC50 9920.0 nM 10.1016/j.bmc.2011.04.043
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 128.0 ug.mL-1 10.1128/aac.00801-08
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1128/aac.00801-08
Staphylococcus aureus Staphylococcus aureus MIC 2.0 ug.mL-1 10.1128/aac.00801-08
Staphylococcus aureus Staphylococcus aureus MIC 4.0 ug.mL-1 10.1128/aac.00801-08
Staphylococcus aureus Staphylococcus aureus MIC 8.0 ug.mL-1 10.1128/aac.00801-08
Staphylococcus epidermidis Staphylococcus epidermidis MIC 0.5 ug.mL-1 10.1128/aac.00801-08
Staphylococcus epidermidis Staphylococcus epidermidis MIC 1.0 ug.mL-1 10.1128/aac.00801-08
None Nucleic Acid Activity 98.0 % 10.1016/j.bmc.2011.04.043
None Nucleic Acid Activity nan None 10.1016/j.bmc.2011.04.043
None Nucleic Acid EC50 1700.0 nM 10.1016/j.bmc.2011.04.043
None Nucleic Acid T1/2 0.75 hr 10.1016/j.bmc.2011.04.043

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001031 *[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O[C@@H]2C[C@@H](O)[C@@H](O)[C@H](C)O2)[C@@H](O)[C@H]1*.CC[C@H](C)[C@H]1C(=O)O[C@H]2c3cc(C)cc(O)c3C3=C(C(=O)c4c(O)cccc4C3=O)N21>>CC[C@H](C)[C@H]1C(=O)O[C@H]2c3cc(C)cc(O)c3C3=C(C(=O)c4c(O[C@H]5C[C@@H](O)[C@@H](O)[C@H](C)O5)cccc4C3=O)N21 MNXR176243
AKRT010163 CC[C@H](C)[C@H]1C(=O)O[C@H]2c3cc(C)cc(O)c3C3=C(C(=O)c4c(O)cccc4C3=O)N21.Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@@H]3C[C@@H](O)[C@@H](O)[C@H](C)O3)O2)c(=O)[nH]c1=O>>CC[C@H](C)[C@H]1C(=O)O[C@H]2c3cc(C)cc(O)c3C3=C(C(=O)c4c(O[C@H]5C[C@@H](O)[C@@H](O)[C@H](C)O5)cccc4C3=O)N21 RXN-11995