{[(2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl]-7-[(2E)-3-{2-[(2S)-4-[(2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamido]butan-2-yl]-1,3-oxazol-4-yl}prop-2-en-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl]oxy}phosphonic acid

• ChemBase ID: 126366
• Molecular Formular: C50H81N4O15P
• Molecular Mass: 1009.169701
• Monoisotopic Mass: 1008.54360454
• SMILES: N#C/C=C(\C=C\C=C(\C(=C\[C@@H](C)[C@@H](O)[C@@H](C)[C@@H](O)C[C@H](OC)[C@H]1O[C@@]2(O[C@H]([C@H]([C@H](O)C2)C)C/C=C/c2nc(oc2)[C@@H](C)CCNC(=O)[C@@H](O)[C@@H](O)[C@@H](N(C)C)COC)C([C@H]1OP(=O)(O)O)(C)C)\C)/C)/C
• Canonical SMILES: COC[C@@H]([C@@H]([C@@H](C(=O)NCC[C@@H](c1occ(n1)/C=C/C[C@@H]1O[C@]2(C[C@H]([C@@H]1C)O)O[C@@H]([C@@H](C2(C)C)OP(=O)(O)O)[C@H](C[C@@H]([C@@H]([C@@H]([C@@H](/C=C(/C(=C/C=C/C(=C\C#N)/C)/C)\C)C)O)C)O)OC)C)O)O)N(C)C
• InChI: InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m0/s1
• InChIKey: FKAWLXNLHHIHLA-YCBIHMBMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl]-7-[(2E)-3-{2-[(2S)-4-[(2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamido]butan-2-yl]-1,3-oxazol-4-yl}prop-2-en-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl]-7-[(2E)-3-{2-[(2S)-4-[(2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamido]butan-2-yl]-1,3-oxazol-4-yl}prop-2-en-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl]oxyphosphonic acid
• Synonyms: Calyculin A from Discodermia calyx; Calyculin

Database IDs

• CAS Number: 101932-71-2
• MDL Number: MFCD06795864
• Beilstein Number: 4903216
• PubChem SID: 162220700; 24892795
• PubChem CID: 10909255; 5311365
• CHEMBL: 384277
• Chemspider ID: 9084513
• Wikipedia Title: Calyculin

CALCULATED PROPERTIES

• Acid pKa: 1.1460295
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): 1.6894811
• LogD (pH = 7.4): 0.49908644
• Log P: 1.7695262
• Molar Refractivity: 267.0961 cm^3
• Polarizability: 103.73827 Å^3
• Polar Surface Area: 286.99 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble
• Apperance: white solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-38
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - C5552

Biochem/physiol Actions
Inhibitor of protein phosphatases types 1 and 2A; marine toxin, potent tumor promotor.