(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 ID: 155981
• Molecular Formular: C99H140N20O17
• Molecular Mass: 1882.2947
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: (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
• Synonyms: Gramicidin A from Bacillus brevis

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 11.539414
• H Acceptors: 17
• H Donor: 21
• LogD (pH = 5.5): 5.4248123
• LogD (pH = 7.4): 5.4247847
• Log P: 5.424813
• Molar Refractivity: 509.6303 cm^3
• Polarizability: 203.29683 Å^3
• Polar Surface Area: 548.99 Å^2
• Rotatable Bonds: 52
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: MD8230000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC)
• Impurities: ≤5% gramicidin C; ≤5% water

DETAILS

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.