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monic acid A | 66262-68-8

分子结构分类

有机化合物 - 脂质和类脂质分子 - 脂肪酰基

中文名称

——

中文别名

——

英文名称

monic acid A

英文别名

monic acid；(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoic acid

CAS

66262-68-8；66290-01-5；70470-39-2

化学式

C₁₇H₂₈O₇

mdl

——

分子量

344.405

InChiKey

IUBMRJVNZLQSHU-FDJBSCRHSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

132-136°C
沸点：

566.3±45.0 °C(Predicted)
密度：

1.270±0.06 g/cm3(Predicted)
溶解度：

可溶于DMSO、乙醇、甲醇

计算性质

辛醇/水分配系数(LogP)：

0.5
重原子数：

24
可旋转键数：

7
环数：

2.0
sp3杂化的碳原子比例：

0.82
拓扑面积：

120
氢给体数：

4
氢受体数：

7

SDS

SDS：812af77d9b152deefd435730736ca33a

查看

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
莫匹罗星	mupirocin	12650-69-0	C₂₆H₄₄O₉	500.63
——	<(2S,3R,4R,5S)-5-<(2S,3S,4S,5S)-(2,3-epoxy-5-hydroxy-4-methylhexyl)>-3,4-dihydroxytetrahydropyran-2-yl>acetone	66262-70-2	C₁₅H₂₆O₆	302.368

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(E)-4-[(2S,3S,4S,5R)-3,4-dihydroxy-5-[[3-[(2S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoic acid	——	C₁₇H₂₈O₇	344.4
——	(E)-5-<(2S,3R,4R,5S)-5-<(2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-methylhexyl>-3,4-dihydroxytetrahydropyran-2-yl>-4-methylpent-3-en-2-one	79959-63-0	C₁₈H₃₀O₆	342.433
莫匹罗星	mupirocin	12650-69-0	C₂₆H₄₄O₉	500.63
——	monamide	——	C₁₇H₂₉NO₆	343.42
——	N-acetonylmonamide	163836-97-3	C₂₀H₃₃NO₇	399.485
——	N-(2-oxobutyl)monamide	——	C₂₁H₃₅NO₇	413.511
——	N-<(ethoxycarbonyl)methyl>monamide	153900-92-6	C₂₁H₃₅NO₈	429.511
——	N-(2-oxohexyl)monamide	173411-61-5	C₂₃H₃₉NO₇	441.565
——	N-<(E)-2-(methoxyimino)propyl>monamide	163836-98-4	C₂₁H₃₆N₂O₇	428.526
——	N-<<(ethylthio)carbonyl>methyl>monamide	173411-69-3	C₂₁H₃₅NO₇S	445.577
——	methyl 11-[[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]amino]-10-oxoundecanoate	173411-63-7	C₂₉H₄₉NO₉	555.709
——	methyl monate A 13-tert-butyldimethylsilyl ether	1314406-69-3	C₂₄H₄₄O₇Si	472.695
——	methyl 6-[[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]amino]-5-oxohexanoate	173411-62-6	C₂₄H₃₉NO₉	485.575
——	(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methyl-N-(2-oxo-2-piperidin-1-ylethyl)but-2-enamide	173411-66-0	C₂₄H₄₀N₂O₇	468.591
——	phenyl 2-[[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]amino]acetate	173411-68-2	C₂₅H₃₅NO₈	477.555
——	S-phenyl 2-[[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]amino]ethanethioate	173411-70-6	C₂₅H₃₅NO₇S	493.621
——	(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-N-[2-(1,3-dithian-2-yl)-2-oxoethyl]-3-methylbut-2-enamide	173411-65-9	C₂₃H₃₇NO₇S₂	503.681
——	monic acid, tris(trimethylsilyl ether)	133674-54-1	C₂₆H₅₃NO₆Si₃	559.966
——	(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methyl-N-(pyridin-2-ylmethyl)but-2-enamide	163836-95-1	C₂₃H₃₄N₂O₆	434.533
——	(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methyl-N-[2-(N-methylanilino)-2-oxoethyl]but-2-enamide	173411-67-1	C₂₆H₃₈N₂O₇	490.597
——	ethyl 2-[[(E)-4-[(2S,3S,4R,5S)-3,4-bis(trimethylsilyloxy)-5-[[(2S,3S)-3-[(2R,3S)-3-trimethylsilyloxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]amino]acetate	1054646-24-0	C₃₀H₅₉NO₈Si₃	646.057
——	N-methoxy-N-methyl-6,7,13-O-tris(trimethylsilyl)monoamide	136380-26-2	C₂₈H₅₇NO₇Si₃	604.02
——	(E)-4-[(2S,3S,4R,5S)-3,4-bis(trimethylsilyloxy)-5-[[(2S,3S)-3-[(2R,3S)-3-trimethylsilyloxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-N-[(2E)-2-methoxyiminopropyl]-3-methylbut-2-enamide	1053629-31-4	C₃₀H₆₀N₂O₇Si₃	645.072
——	methyl 7-ketomonate A 13-tert-butyldimethylsilyl ether	1314406-70-6	C₂₄H₄₂O₇Si	470.679
——	N-(α-cyano-p-methylsulfanylbenzyl)monamide	——	C₂₆H₃₆N₂O₆S	504.648
——	methyl (E)-4-[(2S,3R,4aS,7S,8S,8aS)-3-chloro-8,8a-dihydroxy-2-[(2S,3S)-3-hydroxybutan-2-yl]-3,4,4a,5,7,8-hexahydro-2H-pyrano[3,2-c]pyran-7-yl]-3-methylbut-2-enoate	1314406-73-9	C₁₈H₂₉ClO₇	392.877
——	phenyl 2-[[(E)-4-[(2S,3S,4R,5S)-3,4-bis(trimethylsilyloxy)-5-[[(2S,3S)-3-[(2R,3S)-3-trimethylsilyloxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]amino]acetate	1054661-88-9	C₃₄H₅₉NO₈Si₃	694.101
——	2-[(E)-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-2-methylprop-1-enyl]-1,3-oxazole-5-carbaldehyde	173411-76-2	C₂₀H₂₉NO₇	395.453
——	(E)-4-[(2S,3S,4R,5S)-3,4-bis(trimethylsilyloxy)-5-[[(2S,3S)-3-[(2R,3S)-3-trimethylsilyloxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methyl-N-(pyridin-2-ylmethyl)but-2-enamide	1054799-19-7	C₃₂H₅₈N₂O₆Si₃	651.079
——	methyl (Z)-3-[2-[(E)-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-2-methylprop-1-enyl]-1,3-oxazol-5-yl]prop-2-enoate	173523-09-6	C₂₃H₃₃NO₈	451.517
——	5-(ethylthio)-2-(1-normon-2-yl)oxazole	173411-87-5	C₂₁H₃₃NO₆S	427.562
——	5-butyl-2-(1-normon-2-yl)oxazole	——	C₂₃H₃₇NO₆	423.55
——	methyl 9-[2-[(E)-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-2-methylprop-1-enyl]-1,3-oxazol-5-yl]nonanoate	173411-73-9	C₂₉H₄₇NO₈	537.694
——	(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methyl-N-[2-(5-nitrothiophen-3-yl)-2-oxoethyl]but-2-enamide	1053699-06-1	C₂₃H₃₂N₂O₉S	512.581
——	methyl 4-[2-[(E)-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-2-methylprop-1-enyl]-1,3-oxazol-5-yl]butanoate	173411-72-8	C₂₄H₃₇NO₈	467.56
——	(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methyl-N-[2-(4-nitrothiophen-2-yl)-2-oxoethyl]but-2-enamide	1053652-20-2	C₂₃H₃₂N₂O₉S	512.581

反应信息

作为反应物：

描述：

monic acid A 在三乙胺作用下，以四氢呋喃为溶剂，反应 3.5h，生成 (E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methyl-N-(2-oxo-2-piperidin-1-ylethyl)but-2-enamide

参考文献：

名称：

假单宁酸的化学。15.一系列5-烷基，5-烯基和5-杂取代的恶唑的合成和抗菌活性。

摘要：

描述了一系列5-烷基，5-烯基和5-杂取代的2-（1-正丙基-2-基）恶唑的合成。使用标准琼脂稀释程序，将抗菌活性确定为对一系列革兰氏阳性和革兰氏阴性生物的最小抑制浓度。发现在环上直接或靠近环具有酸官能度的化合物的效力大大降低，而亲脂性随着链长的增加而增加，导致这些衍生物的效力增加。

DOI：

10.1021/jm9503862
作为产物：

描述：

莫匹罗星、 sodium hydroxide 生成 monic acid A

参考文献：

名称：

MANTLE, PETER G.;MACGEORGE, KATHARINE M., J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 255-258

摘要：

DOI：

点击查看最新优质反应信息

文献信息

The Chemistry of Pseudomonic Acid. Part 14. Synthesis and In Vivo Biological Activity of Heterocyclyl Substituted Oxazole Derivatives.

作者：N. J. P. BROOM、J. S. ELDER、P. C. T. HANNAN、J. E. PONS、P. J. O''HANLON、G. WALKER、J. WILSON、P. WOODALL

DOI：10.7164/antibiotics.48.1336

日期：——

heterocyclyl substituted oxazole. Derivatives in which the heterocycle was thiophene, furan, pyridine, or isoxazole showed good antibacterial potency and were further evaluated in vivo. Both pharmacokinetic parameters and oral activity against an experimental intraperitoneal sepsis were superior to results obtained from previously described pseudomonic acid A derivatives.

已制备了含有杂环基取代的恶唑的假单酸A的半合成类似物。杂环为噻吩，呋喃，吡啶或异恶唑的衍生物显示出良好的抗菌效力，并在体内进行了进一步评估。药代动力学参数和针对实验性腹膜内脓毒症的口服活性均优于从先前描述的假单酸A衍生物获得的结果。
The chemistry of pseudomonic acid. Part 4. αβ-Unsaturated ketones derived from monic acid A and its derivatives

作者：Steven Coulton、Peter J. O'Hanlon、Norman H. Rogers

DOI：10.1039/p19820000729

日期：——

Routes to the preparation of αβ-unsaturated ketones (1k–m) have been investigated. n-Butylmanganese(II) chloride was particularly useful for preparing the ketones (1m) from the readily available monic acid A (1b), the nucleus of pseudomonic acid A (1a).

已经研究了制备αβ-不饱和酮（1k–m）的途径。氯化正丁基锰（II）特别适用于从容易获得的单酸A（1a）的核A（1b）中制备酮（1m）。
Antibacterial compounds

申请人：Beecham Group Limited

公开号：US04216223A1

公开（公告）日：1980-08-05

A thiol acid and esters thereof of formula (II): ##STR1## wherein R is hydrogen, a salt forming ion or a pharmaceutically acceptable ester-forming radical, have antibacterial and antimycoplasmal activity and are therefore useful in the treatment of human and veterinary bacterial and mycoplasmal infections.

公式（II）的巯基酸及其酯，其中R为氢，盐形成离子或药学上可接受的酯基，具有抗菌和抗支原体活性，因此可用于治疗人类和兽医细菌和支原体感染。
Programmed Iteration Controls the Assembly of the Nonanoic Acid Side Chain of the Antibiotic Mupirocin

作者：Ashley J. Winter、Matthew T. Rowe、Angus N. M. Weir、Nahida Akter、Sbusisiwe Z. Mbatha、Paul D. Walker、Christopher Williams、Zhongshu Song、Paul R. Race、Christine L. Willis、Matthew P. Crump

DOI：10.1002/anie.202212393

日期：2022.12.12

polyketide fragment, monic acid, is esterified to a 9-hydroxynonanoic acid (9HN) side chain, which is essential for biological activity. NMR spectroscopy, mass spectrometry, chemical probes and in vitro assays were used to establish how 9HN is assembled through the action of multiple acyl carrier proteins, two ketosynthases and fatty acid β-keto processing enzymes.

莫匹罗星是一种临床上重要的抗生素，其中聚酮化合物片段莫尼酸被酯化为 9-羟基壬酸 (9HN) 侧链，这对生物活性至关重要。核磁共振波谱、质谱、化学探针和体外测定用于确定 9HN 如何通过多种酰基载体蛋白、两种酮合成酶和脂肪酸 β-酮加工酶的作用进行组装。
Forrest, Andrew K.; O'Hanlon, Peter J.; Walker, Graham, Journal of the Chemical Society. Perkin transactions I, 1994, # 18, p. 2657 - 2666

作者：Forrest, Andrew K.、O'Hanlon, Peter J.、Walker, Graham

DOI：——

日期：——