(3R,4S,5R,8S,9S,12R)-12-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-[(3S)-3-methyl-4-oxopentyl]-1,7-dioxaspiro[5.5]undecan-2-yl]-5,9-dihydroxy-4-methoxy-2,8-dimethyl-7-oxotridecan-3-yl (3R)-3-hydroxy-3-(4-methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoate

• ChemBase ID: 156055
• Molecular Formular: C41H66O13
• Molecular Mass: 766.95494
• Monoisotopic Mass: 766.45034217
• SMILES: C[C@@H]1CC[C@@]2(CC[C@@H]([C@@H](O2)[C@H](C)CC[C@@H]([C@H](C)C(=O)C[C@H]([C@@H]([C@@H](C(C)C)OC(=O)C[C@H](C2=C(C(=O)OC2=O)C)O)OC)O)O)C)O[C@H]1CC[C@H](C)C(=O)C
• Canonical SMILES: CO[C@H]([C@@H](C(C)C)OC(=O)C[C@H](C1=C(C)C(=O)OC1=O)O)[C@@H](CC(=O)[C@H]([C@H](CC[C@H]([C@@H]1O[C@@]2(CC[C@@H]1C)CC[C@H]([C@@H](O2)CC[C@@H](C(=O)C)C)C)C)O)C)O
• InChI: InChI=1S/C41H66O13/c1-21(2)36(51-34(47)20-31(45)35-27(8)39(48)52-40(35)49)38(50-10)32(46)19-30(44)26(7)29(43)13-11-24(5)37-25(6)16-18-41(54-37)17-15-23(4)33(53-41)14-12-22(3)28(9)42/h21-26,29,31-33,36-38,43,45-46H,11-20H2,1-10H3/t22-,23+,24+,25-,26-,29-,31+,32+,33-,36+,37-,38-,41+/m0/s1
• InChIKey: RFCWHQNNCOJYTR-QKIDKDKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R,8S,9S,12R)-12-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-[(3S)-3-methyl-4-oxopentyl]-1,7-dioxaspiro[5.5]undecan-2-yl]-5,9-dihydroxy-4-methoxy-2,8-dimethyl-7-oxotridecan-3-yl (3R)-3-hydroxy-3-(4-methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoate
• IUPAC Traditional name: (3R,4S,5R,8S,9S,12R)-12-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-[(3S)-3-methyl-4-oxopentyl]-1,7-dioxaspiro[5.5]undecan-2-yl]-5,9-dihydroxy-4-methoxy-2,8-dimethyl-7-oxotridecan-3-yl (3R)-3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate
• Synonyms: Tautomycin from Streptomyces spiroverticillatus

Database IDs

• CAS Number: 109946-35-2
• Beilstein Number: 3583132
• PubChem SID: 162250193
• PubChem CID: 3034761

CALCULATED PROPERTIES

• Acid pKa: 13.519947
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 6.0113225
• LogD (pH = 7.4): 6.011322
• Log P: 6.0113225
• Molar Refractivity: 198.7546 cm^3
• Polarizability: 79.618004 Å^3
• Polar Surface Area: 192.19 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: WX1000000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 22-28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C41H66O13

DETAILS

Sigma Aldrich - 86305

Other Notes
Potent and specific inhibitor of protein phosphatases 1 and 2A1