(2S,3S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-2-{[(2S,4R,5R,6R)-4-{[(2S,4R,5S,6R)-4-{[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-6-{[(2S,4R,5R,6R)-4-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-8,9-dihydroxy-7-methyl-1,2,3,4-tetrahydroanthracen-1-one

• ChemBase编号: 4483
• 分子式: C52H76O24
• 平均质量: 1085.14544
• 单一同位素质量: 1084.47265331
• SMILES: [C@H]1(O[C@@H]([C@H]([C@@](C1)(C)O)O)C)O[C@H]1[C@H]([C@H](O[C@H](C1)O[C@H]1[C@@H]([C@H](O[C@H](C1)O[C@@H]1C(=O)c2c(c3c(c(c(O[C@H]4C[C@H]([C@@H]([C@H](O4)C)O)O[C@@H]4O[C@@H]([C@H]([C@@H](C4)O)O)C)cc3cc2C[C@H]1[C@@H](C(=O)[C@H]([C@H](O)C)O)OC)C)O)O)C)O)C)O
• Canonical SMILES: CO[C@@H]([C@@H]1Cc2cc3cc(O[C@@H]4O[C@H](C)[C@H]([C@@H](C4)O[C@H]4C[C@@H](O)[C@@H]([C@H](O4)C)O)O)c(c(c3c(c2C(=O)[C@H]1O[C@@H]1O[C@H](C)[C@H]([C@@H](C1)O[C@@H]1O[C@H](C)[C@@H]([C@@H](C1)O[C@@H]1O[C@H](C)[C@H]([C@@](C1)(C)O)O)O)O)O)O)C)C(=O)[C@H]([C@H](O)C)O
• InChI: InChI=1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27+,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43-,44-,45+,49+,50+,51-,52+/m1/s1
• InChIKey: CFCUWKMKBJTWLW-BKHRDMLASA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-2-{[(2S,4R,5R,6R)-4-{[(2S,4R,5S,6R)-4-{[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-6-{[(2S,4R,5R,6R)-4-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-8,9-dihydroxy-7-methyl-1,2,3,4-tetrahydroanthracen-1-one
• IUPAC传统名: mith
• 商标名: Mithracin
• 别名: Mithramycin; Plicamycin

登记号

• CAS号: 18378-89-7
• PubChem SID: 160967915
• PubChem CID: 163659

理论计算性质

JChem

• Acid pKa: 8.491704
• 质子受体: 24
• 质子供体: 11
• LogD (pH = 5.5): 2.0724516
• LogD (pH = 7.4): 2.0391889
• Log P: 2.072891
• 摩尔折射率: 257.0091 cm^3
• 极化性: 105.68714 Å^3
• 极化表面积: 358.2 Å^2
• 可自由旋转的化学键: 15
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -0.23
• LOG S: -2.92
• 溶解度: 1.30e+00 g/l

详细说明

DrugBank - DB06810

• Drug Groups: approved; withdrawn
• Description: Plicamycin is an antineoplastic antibiotic produced by Streptomyces plicatus. It has been used in the treatment of testicular cancer, Paget's disease of bone, and, rarely, the management of hypercalcemia. The manufacturer discontinued plicamycin in 2000.
• Indication: For the treatment of testicular cancer, as well as hypercalcemia and hypercalciuria associated with a variety of advanced forms of cancer.
• Pharmacology: Plicamycin is lethal to Hela cells in 48 hours at concentrations as low as 0.5 micrograms per milliliter of tissue culture medium. Plicamycin has shown significant anti-tumor activity against experimental leukemia in mice when administered intraperitoneally.
• Toxicity: The most important form of toxicity associated with the use of plicamycin consists of a dose-related bleeding syndrome which usually begins with an episode of epistaxis. Plicamycin crosses the blood-brain barrier; the concentration found in brain tissue is low but it persists longer than in other tissues.
• Protein Binding: There is no evidence of protein binding, nor is there any evidence of metabolism of the carbohydrate moiety of the drug to carbon dioxide and water with loss through respiration.
• Elimination: Radioautography studies with 3H-labeled plicamycin in mice show that the greatest concentrations of the isotope are in the Kupffer cells of the liver and cells of the renal tubules. Plicamycin is rapidly cleared from the blood within the first 2 hours and excretion is also rapid. 67% percent of measured excretion occurs within 4 hours, 75% within 8 hours, and 90% is recovered in the first 24 hours after injection.
• References: Wohlert SE, Kunzel E, Machinek R, Mendez C, Salas JA, Rohr J: The structure of mithramycin reinvestigated. J Nat Prod. 1999 Jan;62(1):119-21. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Wohlert SE, Kunzel E, Machinek R, Mendez C, Salas JA, Rohr J: The structure of mithramycin reinvestigated. J Nat Prod. 1999 Jan;62(1):119-21. Pubmed