{[(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编号: 126366
• 分子式: C50H81N4O15P
• 平均质量: 1009.169701
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: {[(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传统名: [(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
• 别名: Calyculin A from Discodermia calyx; Calyculin

登记号

• CAS号: 101932-71-2
• MDL号: MFCD06795864
• Beilstein号: 4903216
• PubChem SID: 24892795; 162220700
• PubChem CID: 5311365; 10909255
• CHEMBL: 384277
• Chemspider ID: 9084513
• 维基百科标题: Calyculin

理论计算性质

• Acid pKa: 1.1460295
• 质子受体: 16
• 质子供体: 8
• LogD (pH = 5.5): 1.6894811
• LogD (pH = 7.4): 0.49908644
• Log P: 1.7695262
• 摩尔折射率: 267.0961 cm^3
• 极化性: 103.73827 Å^3
• 极化表面积: 286.99 Å^2
• 可自由旋转的化学键: 26
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: soluble; ethanol: soluble
• 外观: white solid

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 3462
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 23/24/25-38
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H311-H315-H331
• GHS警示性声明: P261-P280-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 3
• 保存温度: -20°C

产品相关信息

• 纯度: ≥90% (HPLC)

详细说明

Sigma Aldrich - C5552

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