(3S)-3-{[(3S,6S,9R,15S,18R,21S,24R,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2R)-3-carbamoyl-2-[(2S)-2-decanamido-3-(1H-indol-3-yl)propanamido]propanamido]propanoic acid

• ChemBase编号: 154366
• 分子式: C72H101N17O26
• 平均质量: 1620.67064
• 单一同位素质量: 1619.71036644
• SMILES: CCCCCCCCCC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H]1[C@H](OC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)CNC1=O)CCCN)CC(=O)O)C)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)c1ccccc1N)C
• Canonical SMILES: NCCC[C@H]1NC(=O)CNC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](Cc2c[nH]c3c2cccc3)NC(=O)CCCCCCCCC)CC(=O)N)CC(=O)O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC1=O)CC(=O)O)C)CC(=O)O)CO)[C@@H](CC(=O)O)C)CC(=O)c1ccccc1N
• InChI: InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43-,44+,45-,46+,47+,48+,49+,50-,60+,61+/m1/s1
• InChIKey: DOAKLVKFURWEDJ-FAZHXZQASA-N

名称和登记号

名称

• IUPAC标准名: (3S)-3-{[(3S,6S,9R,15S,18R,21S,24R,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2R)-3-carbamoyl-2-[(2S)-2-decanamido-3-(1H-indol-3-yl)propanamido]propanamido]propanoic acid
• IUPAC传统名: (3S)-3-{[(3S,6S,9R,15S,18R,21S,24R,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2R)-3-carbamoyl-2-[(2S)-2-decanamido-3-(1H-indol-3-yl)propanamido]propanamido]propanoic acid
• 别名: Dapcin; Daptomycin

登记号

• CAS号: 103060-53-3
• PubChem SID: 162248505
• PubChem CID: 71311849

理论计算性质

• Acid pKa: 2.9766474
• 质子受体: 27
• 质子供体: 22
• LogD (pH = 5.5): -14.167885
• LogD (pH = 7.4): -18.900747
• Log P: -9.365402
• 摩尔折射率: 393.5654 cm^3
• 极化性: 155.05566 Å^3
• 极化表面积: 702.02 Å^2
• 可自由旋转的化学键: 35
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: soluble; ethanol: soluble; methanol: soluble

安全信息

• 德国WGK号: 3
• 保存温度: -20°C

产品相关信息

• 纯度: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C72H101N17O26

详细说明

Sigma Aldrich - D2446

Biochem/physiol Actions
Cyclic lipopeptide antibiotic effective against gram-positive bacteria. Derived from a fermentation product of Streptomyces sp. Its distinct mechanism of action, disrupting plamsa membrane function, makes it useful against resistant bacteria. Potential therapy for Staphylococcus aureus infections, including MRSA (methicillin-resistant Staphylococcus aureus).
Daptomycin disrupts plasma membrane function, which makes it useful against resistant bacteria. It is thought to cause rapid depolarization thereby inhibiting protein, DNA and RNA synthesis.
Application
Daptomycin is a cyclic lipopeptide antibiotic effective against gram-positive bacteria. It is derived from a fermentation product of Streptomyces sp. It is useful against resistant bacteria. It is a potential therapy for Staphylococcus aureus infections1, including MRSA (methicillin-resistant Staphylococcus aureus). It has also been studied as a potential therapy for Streptococcus pneumoniae infections 2. It has been used to study the impact of sarA on daptomycin susceptibility of Staphylococcus aureus.3