Basic information
- CAS
54526-94-2- Standard SMILES
COc1cc(O)c2c(c1)C(=O)c1cc3c(c(O)c1C2=O)C(O[C@@H]1O[C@@H](C)[C@H](OC)[C@@H](O)[C@H]1OC)C(OC)C(C)(O)C3=O- InChIKey
VHJWDTPKSIFZBV-NIVUTRQNSA-N- Molecular formula
- C29H32O13
- Average molar mass
- 588.6 g/mol
- Monoisotopic mass
- 588.18429107
Overview
3'-O-methylsteffimycin is an anthracycline.
Names & identifiers
- Preferred name
- 2,5,7-trihydroxy-4-[(2S,3R,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy-3,9-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trione
- IUPAC
- 2,5,7-trihydroxy-4-[(2S,3R,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy-3,9-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trione
- English name
- STEFFIMYCIN B
- Molecular formula
- C29H32O13
- Molecular weight
- 588.56
Names & synonyms
3'-O-methylsteffimycin2,5,7-trihydroxy-4-[(2S,3R,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy-3,9-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trioneU 4061554526-94-2NSC2048551,6,11(2H)-Naphthacenetrione, 4-((6-deoxy-2,4-di-O-methyl-alpha-L-mannopyranosyl)oxy)-3,4-dihydro-2,5,7-trihydroxy-3,9-dimethoxy-2-methyl-CHEBI:2147722,5,7-trihydroxy-4-[(2S,3R,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyl-tetrahydropyran-2-yl]oxy-3,9-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trioneu40615Nsc 204855STEFFIMYCIN BSteffimycin 4'-methyl ether
Show more names
5,7-trihydroxy-3,9-dimethoxy-2-methyl-l)oxy)-4-dihydro-21,6,11(2h)-naphthacenetrione,4-((6-deoxy-2,4-di-o-methyl-alpha-l-mannopyranosy4-(2-O,4-O-Dimethyl-α-L-rhamnopyranosyloxy)-3,4-dihydro-2,5,7-trihydroxy-3,9-dimethoxy-2-methyl-1,6,11(2H)-naphthacenetrione4-[(2-O,4-O-Dimethyl-6-deoxy-α-L-mannopyranosyl)oxy]-3,4-dihydro-2,5,7-trihydroxy-3,9-dimethoxy-2-methyl-1,6,11(2H)-naphthacenetrione1,6,11(2H)-Naphthacenetrione, 4-[(6-deoxy-2,4-di-O-methyl-α-L-mannopyranosyl)oxy]-3,4-dihydro-2,5,7-trihydroxy-3,9-dimethoxy-2-methyl-, (2S,3S,4R)-
Database identifiers
- CAS
54526-94-2- PubChem CID
- 504167
- ChEBI
CHEBI:214772- Nikkaji
- J85.479D
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 188 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 6
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 1,050
Physicochemical properties
- Boiling point
- 801.2 · 801.2±65.0 °C(Predicted)
- Density
- 1.52 · 1.52±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
- form
- A lyophilisate
- pka
- 5.09 · 5.09±0.70(Predicted)
Chemistry & industry
Applications
UsesSteffimycin B is an anthracycline metabolite isolated from a Streptomyces sp., with antibacterial and antineoplastic properties. Crystallographic studies of binding to DNA suggest that it has a higher CpG base sequence specificity over the TpA step, similar to that of daunorubicin and nogalamycin. A close analogue was shown to be active against ras oncogene-expressed cells.
Suppliers14 total
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
TargetMol 中国（陶术生物）400-821-0310 15002144251 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
西安莱茵生物科技有限公司86-(0)29-85992781 17792393971 · [email protected]
Novachemistry44-20819178-90 02081917890 · [email protected]
上海宏叶生物科技有限公司400-9205774 400-920-5774 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
陕西西化化学工业有限公司18161915376 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
武汉丽合智造生物科技有限公司18971458902 · [email protected]
Related reactions
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Compound notes
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