(2R,3S,4R,6R)-6-{[(2S,4R,5S)-2-{4-[(4Z,6Z,14Z,16E)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxypentan-2-yl}-2-hydroxy-5-methyl-6-[(1E)-prop-1-en-1-yl]oxan-4-yl]oxy}-4-hydroxy-2-methyloxan-3-yl carbamate

• ChemBase ID: 132555
• Molecular Formular: C46H75NO14
• Molecular Mass: 866.086
• Monoisotopic Mass: 865.51875609
• SMILES: CCC1C(C(C/C(=C\C=C/C(C(OC(=O)/C(=C\C(=C/C(C1O)C)\C)/OC)C(C)C(C(C)[C@@]1(C[C@H]([C@@H](C(O1)/C=C/C)C)O[C@H]1C[C@H]([C@@H]([C@H](O1)C)OC(=O)N)O)O)O)OC)/C)C)O
• Canonical SMILES: C/C=C/C1O[C@@](O)(C[C@H]([C@@H]1C)O[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)OC(=O)N)C(C(C(C1OC(=O)/C(=C\C(=C/C(C)C(O)C(C(C(C/C(=C\C=C/C1OC)/C)C)O)CC)\C)/OC)C)O)C
• InChI: InChI=1S/C46H75NO14/c1-13-16-34-28(7)37(58-38-22-33(48)43(31(10)57-38)60-45(47)53)23-46(54,61-34)30(9)41(51)29(8)42-35(55-11)18-15-17-24(3)19-26(5)39(49)32(14-2)40(50)27(6)20-25(4)21-36(56-12)44(52)59-42/h13,15-18,20-21,26-35,37-43,48-51,54H,14,19,22-23H2,1-12H3,(H2,47,53)/b16-13+,18-15-,24-17-,25-20-,36-21+/t26?,27?,28-,29?,30?,31-,32?,33-,34?,35?,37-,38+,39?,40?,41?,42?,43-,46+/m1/s1
• InChIKey: DJZCTUVALDDONK-RIZUKJEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,6R)-6-{[(2S,4R,5S)-2-{4-[(4Z,6Z,14Z,16E)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxypentan-2-yl}-2-hydroxy-5-methyl-6-[(1E)-prop-1-en-1-yl]oxan-4-yl]oxy}-4-hydroxy-2-methyloxan-3-yl carbamate
• IUPAC Traditional name: (2R,3S,4R,6R)-6-{[(2S,4R,5S)-2-{4-[(4Z,6Z,14Z,16E)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxypentan-2-yl}-2-hydroxy-5-methyl-6-[(1E)-prop-1-en-1-yl]oxan-4-yl]oxy}-4-hydroxy-2-methyloxan-3-yl carbamate
• Synonyms: Folimycin; Concanamycin A

Database IDs

• CAS Number: 80890-47-7
• MDL Number: MFCD00210037
• Beilstein Number: 3560277
• PubChem SID: 162226832; 24893186
• PubChem CID: 71308575

CALCULATED PROPERTIES

• Acid pKa: 11.676701
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): 5.5929136
• LogD (pH = 7.4): 5.5928907
• Log P: 5.5929136
• Molar Refractivity: 232.6526 cm^3
• Polarizability: 91.369026 Å^3
• Polar Surface Area: 225.92 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: CB9732000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• 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, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥70% (HPLC)

DETAILS

Sigma Aldrich - C9705

Biochem/physiol Actions
Cytotoxic. Inhibits acidification of organelles and perforin-mediated cytotoxicity.