(7R,8R,9S,10S,11R,17S,18R)-18-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-4-{[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-2-hydroxy-5-methyl-6-(prop-1-en-1-yl)oxan-2-yl]-3-hydroxypentan-2-yl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyl-1-oxacyclooctadeca-3,5,13,15-tetraen-2-one

• ChemBase ID: 153653
• Molecular Formular: C45H74O13
• Molecular Mass: 823.06126
• Monoisotopic Mass: 822.51294243
• SMILES: CC[C@@H]1[C@H]([C@@H](C/C(=C/C=C[C@@H]([C@@H](OC(=O)/C(=C/C(=C/[C@H]([C@H]1O)C)/C)/OC)[C@@H](C)[C@H]([C@H](C)C1(C[C@H]([C@@H]([C@H](O1)/C=C/C)C)O[C@H]1C[C@H]([C@@H]([C@H](O1)C)O)O)O)O)OC)/C)C)O
• Canonical SMILES: C/C=C/[C@H]1OC(O)(C[C@H]([C@@H]1C)O[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)O)[C@H]([C@@H]([C@@H]([C@@H]1OC(=O)/C(=C/C(=C/[C@@H](C)[C@@H](O)[C@@H]([C@H]([C@@H](C/C(=C/C=C[C@@H]1OC)/C)C)O)CC)/C)/OC)C)O)C
• InChI: InChI=1S/C45H74O13/c1-13-16-34-28(7)37(56-38-22-33(46)42(50)31(10)55-38)23-45(52,58-34)30(9)41(49)29(8)43-35(53-11)18-15-17-24(3)19-26(5)39(47)32(14-2)40(48)27(6)20-25(4)21-36(54-12)44(51)57-43/h13,15-18,20-21,26-35,37-43,46-50,52H,14,19,22-23H2,1-12H3/t26-,27-,28-,29+,30+,31-,32+,33-,34-,35+,37-,38+,39+,40-,41-,42-,43-,45-/m1/s1
• InChIKey: XKYYLWWOGLVPOR-RSURHUDISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R,8R,9S,10S,11R,17S,18R)-18-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-4-{[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-2-hydroxy-5-methyl-6-(prop-1-en-1-yl)oxan-2-yl]-3-hydroxypentan-2-yl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyl-1-oxacyclooctadeca-3,5,13,15-tetraen-2-one
• IUPAC Traditional name: (7R,8R,9S,10S,11R,17S,18R)-18-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-4-{[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-2-hydroxy-5-methyl-6-(prop-1-en-1-yl)oxan-2-yl]-3-hydroxypentan-2-yl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyl-1-oxacyclooctadeca-3,5,13,15-tetraen-2-one
• Synonyms: Concanamycin C from Streptomyces sp.

Database IDs

• CAS Number: 81552-34-3
• MDL Number: MFCD00216692
• Beilstein Number: 6628190
• PubChem SID: 162247792
• PubChem CID: 71311712

CALCULATED PROPERTIES

• Acid pKa: 11.664953
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): 5.4853334
• LogD (pH = 7.4): 5.4853106
• Log P: 5.485334
• Molar Refractivity: 224.8244 cm^3
• Polarizability: 88.2104 Å^3
• Polar Surface Area: 193.83 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: GK6887000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28-36
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H319-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P305 + P351 + P338
• 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 1
• Storage Temperature: -20°C

Product Information

• Purity: ~95% (HPLC)
• Empirical Formula (Hill Notation): C45H74O13

DETAILS

Sigma Aldrich - 27691

Application
Cancanamycin C, a vacuolar AT Pase, is used to suppress antigen presentation by MHC class II molecules. V-ATPases are responsible for the acidification of eukaryotic organelles such as endosomes and lysosomes and the vacuoles of plants and fungi 1
Biochem/physiol Actions
Concanamycin C inhibits v-ATPase (vacuolar-ATPase) and perturbs vacuolar organelle, endosome, and lysosome acidification processes. Used to suppress antigen presentation by MHC class II molecules.
Concanamycin C inhibits v-ATPase (vacuolar-ATPase) and perturbs vacuolar organelle, endosome, and lysosome acidification processes. Vacuolar ATPases, such as Concanamycin C, pump protons into the lumen of various endomembrane systems and cellular compartments 1.