(2R)-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-[(2-hydroxyethyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]-2-[(2S)-2-{2-[(2S)-2-formamido-3-methylbutanamido]acetamido}propanamido]-4-methylpentanamide

• ChemBase编号: 155981
• 分子式: C99H140N20O17
• 平均质量: 1882.2947
• 单一同位素质量: 1881.07053312
• SMILES: C[C@@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)NCCO)NC(=O)CNC(=O)[C@H](C(C)C)NC=O
• Canonical SMILES: OCCNC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](C(C)C)NC=O)C)CC(C)C)C)CC(C)C)CC(C)C)CC(C)C
• InChI: InChI=1S/C99H140N20O17/c1-51(2)37-73(109-86(123)59(17)107-81(122)49-105-96(133)82(55(9)10)106-50-121)89(126)108-60(18)87(124)117-84(57(13)14)98(135)119-85(58(15)16)99(136)118-83(56(11)12)97(134)116-80(44-64-48-104-72-34-26-22-30-68(64)72)95(132)112-76(40-54(7)8)92(129)115-79(43-63-47-103-71-33-25-21-29-67(63)71)94(131)111-75(39-53(5)6)91(128)114-78(42-62-46-102-70-32-24-20-28-66(62)70)93(130)110-74(38-52(3)4)90(127)113-77(88(125)100-35-36-120)41-61-45-101-69-31-23-19-27-65(61)69/h19-34,45-48,50-60,73-80,82-85,101-104,120H,35-44,49H2,1-18H3,(H,100,125)(H,105,133)(H,106,121)(H,107,122)(H,108,126)(H,109,123)(H,110,130)(H,111,131)(H,112,132)(H,113,127)(H,114,128)(H,115,129)(H,116,134)(H,117,124)(H,118,136)(H,119,135)/t59-,60-,73+,74+,75+,76+,77-,78-,79-,80-,82-,83+,84+,85-/m0/s1
• InChIKey: ZWCXYZRRTRDGQE-LUPIJMBPSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-[(2-hydroxyethyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]-2-[(2S)-2-{2-[(2S)-2-formamido-3-methylbutanamido]acetamido}propanamido]-4-methylpentanamide
• IUPAC传统名: (2R)-N-[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-[(2-hydroxyethyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]-2-[(2S)-2-{2-[(2S)-2-formamido-3-methylbutanamido]acetamido}propanamido]-4-methylpentanamide
• 别名: Gramicidin A from Bacillus brevis

登记号

• CAS号: 11029-61-1
• EC号: 234-259-8
• MDL号: MFCD00466944
• Beilstein号: 6461131
• PubChem SID: 162250119
• PubChem CID: 16132269

理论计算性质

• Acid pKa: 11.539414
• 质子受体: 17
• 质子供体: 21
• LogD (pH = 5.5): 5.4248123
• LogD (pH = 7.4): 5.4247847
• Log P: 5.424813
• 摩尔折射率: 509.6303 cm^3
• 极化性: 203.29683 Å^3
• 极化表面积: 548.99 Å^2
• 可自由旋转的化学键: 52
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: MD8230000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥90% (HPLC)
• 杂质: ≤5% gramicidin C; ≤5% water

详细说明

Sigma Aldrich - 50845

Amino Acid Sequence
HCO-X-Gly-L-Ala-D-Leu-L-Ala-D-Val-L-Val-D-Val-L-Trp-D-Leu-L-Trp-D-Leu-L-Trp-D-Leu-L-Trp-NHCH2CH2OH
Biochem/physiol Actions
Gramicidin A is a polypeptide antibiotic that forms single ion monovalent cation channels in biological membranes.
Gramicidin A increases the permeability of bacterial cell membranes which allows inorganic monovalent cations to travel through unrestricted. This destroys the ion gradient between the cytoplasm and the extracellular environment 4.
Application
Gramicidin A is a linear pentadecapeptide antibiotic which is used for studies on bacterial cell wall permeabilization and monovalent cation channel formation. Gramicidin has also been shown to inhibit transcription of T7 phage DNA, inhibit membrane-bound epidennal adenosine triphosphatase, suppress human lymphocyte blastogenesis in vitro and prolong heart allograft survival in the rat model 1,2,3.