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leukaemomycins d

AlkaPlorer ID: AK005329

Synonym: 'Daunomycinol'

IUPAC Name: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(1-hydroxyethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

Structure

SMILES: COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(C)O)C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(O)=C1C2=O

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InChI: InChI=1S/C27H31NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10-11,14,16-17,22,29-30,32,34-35H,7-9,28H2,1-3H3/t10-,11?,14-,16-,17-,22+,27-/m0/s1

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InChIKey: HJEZFVLKJYFNQW-FKKRWUELSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Streptomyces griseus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 529.5420000000003

TPSA？: 189.0

MolLogP？: 0.8206999999999991

Number of H-Donors: 6

Number of H-Acceptors: 11

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Mus musculus L1210 Drug uptake 0.33 nmol 10.1021/jm00227a015
Mus musculus L1210 Inhibition 11.2 % 10.1021/jm00227a015
Mus musculus L1210 Inhibition 12.1 % 10.1021/jm00227a015
Mus musculus L1210 Inhibition 28.9 % 10.1021/jm00227a015
Mus musculus L1210 Inhibition 30.8 % 10.1021/jm00227a015
Mus musculus L1210 Inhibition 36.8 % 10.1021/jm00227a015
Mus musculus L1210 Inhibition 46.4 % 10.1021/jm00227a015
Mus musculus L1210 Ratio 88.0 None 10.1021/jm00227a015
Mus musculus L1210 Ratio 94.0 None 10.1021/jm00227a015

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT006649 CC(O)[C@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1)C(=O)c1c(O)cccc1C3=O.C[33S]>>COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 None
AKRT006650 CC(O)[C@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1)C(=O)c1c(O)cccc1C3=O.C[SAH]>>COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 RXN-14833
AKRT010309 CC[C@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1)C(=O)c1c(OC)cccc1C3=O>>COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 RXN-14829
AKRT011964 COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)=O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1>>COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 63504
AKRT011966 COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1>>COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)=O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 RXN-14830