papyriferic acid | 78782-15-7

分子结构分类

有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质

中文名称

——

中文别名

——

英文名称

papyriferic acid

英文别名

3-[[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3-oxopropanoic acid

CAS

78782-15-7

化学式

C₃₅H₅₆O₈

mdl

——

分子量

604.825

InChiKey

RLVAVWQAAQFUOP-GNYBQDBLSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

658.4±55.0 °C(Predicted)
密度：

1.17±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

6.7
重原子数：

43
可旋转键数：

8
环数：

5.0
sp3杂化的碳原子比例：

0.91
拓扑面积：

119
氢给体数：

2
氢受体数：

8

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	3-(O-iso-butylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-50-3	C₃₉H₆₄O₈	660.932
——	methyl papyriferate	78782-16-8	C₃₆H₅₈O₈	618.852
——	3-(O-heptylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-44-5	C₄₂H₇₀O₈	703.013
——	3-(O-hexylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-43-4	C₄₁H₆₈O₈	688.986
——	3-(O-butylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-41-2	C₃₉H₆₄O₈	660.932
——	3-(O-ethylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-39-8	C₃₇H₆₀O₈	632.879
——	3-(O-pentylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-42-3	C₄₀H₆₆O₈	674.959
——	3-(O-octylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-45-6	C₄₃H₇₂O₈	717.04
——	3-(O-tert-butylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-47-8	C₃₉H₆₄O₈	660.932
——	3-(O-allylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-46-7	C₃₈H₆₀O₈	644.89
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-amino-3-oxopropanoate	1228638-60-5	C₃₅H₅₇NO₇	603.84
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(methylamino)-3-oxopropanoate	1228638-61-6	C₃₆H₅₉NO₇	617.867
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(ethylamino)-3-oxopropanoate	1228638-62-7	C₃₇H₆₁NO₇	631.894
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(dimethylamino)-3-oxopropanoate	1228638-72-9	C₃₇H₆₁NO₇	631.894
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-oxo-3-(propylamino)propanoate	1228638-63-8	C₃₈H₆₃NO₇	645.921
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-oxo-3-(pentylamino)propanoate	1228638-65-0	C₄₀H₆₇NO₇	673.974
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(tert-butylamino)-3-oxopropanoate	1228638-70-7	C₃₉H₆₅NO₇	659.948
——	3α,12β,25-trihydroxy-20S,24R-epoxydammarane	19942-05-3	C₃₀H₅₂O₄	476.74
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(nonylamino)-3-oxopropanoate	1228638-66-1	C₄₄H₇₅NO₇	730.082
——	3-(O-benzylmalonyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-48-9	C₄₂H₆₂O₈	694.949
——	3-O-(morpholino-β-oxopropanoyl)-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane	1228638-71-8	C₃₉H₆₃NO₈	673.931
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-anilino-3-oxopropanoate	1228638-68-3	C₄₁H₆₁NO₇	679.938
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(benzylamino)-3-oxopropanoate	1228638-67-2	C₄₂H₆₃NO₇	693.965
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-4,4,8,10,14-pentamethyl-17-[(2S,5R)-2-methyl-5-[2-[2-oxo-2-(propylamino)acetyl]oxypropan-2-yl]oxolan-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-oxo-3-(propylamino)propanoate	1228638-73-0	C₄₃H₇₀N₂O₉	759.037
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-4,4,8,10,14-pentamethyl-17-[(2S,5R)-2-methyl-5-[2-[2-oxo-2-(pentylamino)acetyl]oxypropan-2-yl]oxolan-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-oxo-3-(pentylamino)propanoate	1228638-74-1	C₄₇H₇₈N₂O₉	815.144
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-4,4,8,10,14-pentamethyl-17-[(2S,5R)-2-methyl-5-[2-[2-(nonylamino)-2-oxoacetyl]oxypropan-2-yl]oxolan-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(nonylamino)-3-oxopropanoate	1228638-75-2	C₅₅H₉₄N₂O₉	927.359
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-[2-[2-(tert-butylamino)-2-oxoacetyl]oxypropan-2-yl]-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(tert-butylamino)-3-oxopropanoate	1228638-79-6	C₄₅H₇₄N₂O₉	787.091
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-[2-(2-anilino-2-oxoacetyl)oxypropan-2-yl]-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-anilino-3-oxopropanoate	1228638-77-4	C₄₉H₆₆N₂O₉	827.071
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-[2-[2-(benzylamino)-2-oxoacetyl]oxypropan-2-yl]-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(benzylamino)-3-oxopropanoate	1228638-76-3	C₅₁H₇₀N₂O₉	855.125
——	[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(2,5-dimethoxyanilino)-3-oxopropanoate	1228638-69-4	C₄₃H₆₅NO₉	739.99

反应信息

作为反应物：

描述：

papyriferic acid 在氢氧化钾作用下，以乙醇为溶剂，反应 1.0h，以84%的产率得到3α,12β,25-trihydroxy-20S,24R-epoxydammarane

参考文献：

名称：

Papyriferic acid: a triterpenoid from Alaskan paper birch

摘要：

DOI：

10.1021/jo00335a054

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文献信息

Papyriferic acid derivatives as reversal agents of multidrug resistance in cancer cells

作者：Juan Xiong、Masatoshi Taniguchi、Yoshiki Kashiwada、Michiko Sekiya、Takashi Yamagishi、Yoshihisa Takaishi

DOI：10.1016/j.bmc.2010.02.046

日期：2010.4

Forty-one derivatives of papyriferic acid were prepared based on our previous finding that methyl papyriferate (3) showed potent reversing effect on cytotoxicity of colchicine against multidrug resistance (MDR) human cancer cells (KB-C2), and evaluated for their cytotoxicity and effect on reversing P-gp-mediated MDR against KB-C2 cells. 3-O-(Morpholino-b-oxopropanoyl)-12 beta-acetoxy-3 alpha,25-dihydroxy-(20S,24R)-epoxydammarane (37) significantly increased the sensitivity of colchicine against KB-C2 cells by 185-fold at 5 mu g/mL (7.4 mu M), and the cytotoxicity of colchicine was recovered to nearly that of sensitive (KB) cells. The other several new amide derivatives also exhibited potent reversal activity comparable to or more potent than methyl papyriferate and verapamil. (C) 2010 Elsevier Ltd. All rights reserved.
Papyriferic acid: a triterpenoid from Alaskan paper birch

作者：Paul B. Reichardt

DOI：10.1021/jo00335a054

日期：1981.10