10-{4-Dimethylamino-5-[4-Hydroxy-6-Methyl-5-(6-Methyl-5-Oxo-Tetrahydro-Pyran-2-Yloxy)-Tetrahydro-Pyrane-2-Yloxy]-6-Methyl-Tetrahydro-Pyran-2-Yloxy}-8-Ethyl-1,8,11-Trihydroxy-7,8,9,10-Tetrahydro-Naphthacene-5,12-Dione

Status : experimental

Chemical Classification

This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Anthracyclines

Organic compounds

Phenylpropanoids and polyketides

Anthracyclines

Calculated Property

kind Value Source
logP 2.94 ALOGPS
logS -3.8 ALOGPS
Water Solubility 1.34e-01 g/l ALOGPS
logP 4.99 ChemAxon
IUPAC Name (8S,10S)-10-{[(2R,4R,5S,6R)-4-(dimethylamino)-5-{[(2S,4R,5R,6R)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-8-ethyl-1,8,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione ChemAxon
Traditional IUPAC Name (8S,10S)-10-{[(2R,4R,5S,6R)-4-(dimethylamino)-5-{[(2S,4R,5R,6R)-4-hydroxy-6-methyl-5-{[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-8-ethyl-1,8,11-trihydroxy-9,10-dihydro-7H-tetracene-5,12-dione ChemAxon
Molecular Weight 753.8318 ChemAxon
Monoisotopic Weight 753.336040723 ChemAxon
SMILES CC[C@@]1(O)C[C@H](O[C@H]2C[C@H]([C@H](O[C@H]3C[C@@H](O)[C@@H](O[C@H]4CCC(=O)[C@H](C)O4)[C@@H](C)O3)[C@@H](C)O2)N(C)C)C2=C(O)C3=C(C=C2C1)C(=O)C1=CC=CC(O)=C1C3=O ChemAxon
Molecular Formula C40H51NO13 ChemAxon
InChI InChI=1S/C40H51NO13/c1-7-40(48)16-21-13-23-34(37(47)33-22(35(23)45)9-8-10-26(33)43)36(46)32(21)28(17-40)52-30-14-24(41(5)6)38(19(3)50-30)54-31-15-27(44)39(20(4)51-31)53-29-12-11-25(42)18(2)49-29/h8-10,13,18-20,24,27-31,38-39,43-44,46,48H,7,11-12,14-17H2,1-6H3/t18-,19+,20+,24+,27+,28-,29-,30-,31-,38+,39-,40-/m0/s1 ChemAxon
InChIKey InChIKey=OXPCRXLITLBLEY-GJBXPKINSA-N ChemAxon
Polar Surface Area (PSA) 190.75 ChemAxon
Refractivity 193.01 ChemAxon
Polarizability 81.06 ChemAxon
Rotatable Bond Count 8 ChemAxon
H Bond Acceptor Count 14 ChemAxon
H Bond Donor Count 4 ChemAxon
pKa (strongest acidic) 8.94 ChemAxon
pKa (strongest basic) 8.22 ChemAxon
Physiological Charge 1 ChemAxon
Number of Rings 7 ChemAxon
Bioavailability 0 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 1 ChemAxon

Target within organism

  • RdmC : in Streptomyces purpurascens