{[2-(14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl)-7-[3-(2-{4-[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: 105076
• Molecular Formular: C50H81N4O15P
• Molecular Mass: 1009.169701
• Monoisotopic Mass: 1008.54360454
• SMILES: COCC(C(O)C(O)C(=O)NCCC(C)c1nc(co1)/C=C\CC1OC2(CC(O)C1C)OC(C(CC(O)C(C)C(O)C(C)/C=C(/C)\C(=C\C=C\C(=C\C#N)\C)\C)OC)C(OP(=O)(O)O)C2(C)C)N(C)C
• Canonical SMILES: COCC(C(C(C(=O)NCCC(c1occ(n1)/C=C\CC1OC2(CC(C1C)O)OC(C(C2(C)C)OP(=O)(O)O)C(CC(C(C(C(/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)
• InChIKey: FKAWLXNLHHIHLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[2-(14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl)-7-[3-(2-{4-[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: [2-(14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl)-7-[3-(2-{4-[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

Database IDs

• CAS Number: 101932-71-2
• PubChem SID: 162092312
• PubChem CID: 71299719

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

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: ≥95%

DETAILS

MP Biomedicals - 02158378

Purity: >95%
Phosphatase inhibitor with very potent inhibitory activity against both PP1 and PP2A phosphatases.
IC₅₀ values of approximately 1 nm for both PP1 and PP2A.

REFERENCES

• Ishihara, H., et al., Biochem. Biophys. Res. Commun. , 159 : 871 (1989).
• Suganuma, M., et al., Cancer Res. , 50 : 3521 (1990).