(2S)-6-amino-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-4-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-N-[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]hexanamide

• ChemBase ID: 131028
• Molecular Formular: C100H132N26O13
• Molecular Mass: 1906.28448
• Monoisotopic Mass: 1905.04671841
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCNC(=N)N)CCCNC(=N)N)Cc1c[nH]c2c1cccc2)Cc1c[nH]c2c1cccc2)Cc1c[nH]c2c1cccc2)Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)N)CC(C)C
• InChI: InChI=1S/C100H132N26O13/c1-5-57(4)85(102)95(136)123-79(45-56(2)3)96(137)124-42-20-36-82(124)92(133)118-76(46-58-51-110-68-28-11-6-23-63(58)68)89(130)116-74(33-16-17-39-101)88(129)121-80(49-61-54-113-71-31-14-9-26-66(61)71)97(138)125-43-21-38-84(125)94(135)120-78(48-60-53-112-70-30-13-8-25-65(60)70)91(132)122-81(50-62-55-114-72-32-15-10-27-67(62)72)98(139)126-44-22-37-83(126)93(134)119-77(47-59-52-111-69-29-12-7-24-64(59)69)90(131)117-75(35-19-41-109-100(106)107)87(128)115-73(86(103)127)34-18-40-108-99(104)105/h6-15,23-32,51-57,73-85,110-114H,5,16-22,33-50,101-102H2,1-4H3,(H2,103,127)(H,115,128)(H,116,130)(H,117,131)(H,118,133)(H,119,134)(H,120,135)(H,121,129)(H,122,132)(H,123,136)(H4,104,105,108)(H4,106,107,109)/t57-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-/m0/s1
• InChIKey: USSYUMHVHQSYNA-SLDJZXPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-4-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-N-[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]hexanamide
• IUPAC Traditional name: (2S)-6-amino-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-4-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-N-[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}butyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]hexanamide
• Synonyms: Ile-Leu-Pro-Trp-Lys-Trp-Pro-Trp-Trp-Pro-Trp-Arg-Arg-NH2; Indolicidin

Database IDs

• CAS Number: 140896-21-5
• PubChem SID: 162225306
• PubChem CID: 16129733

CALCULATED PROPERTIES

• Acid pKa: 12.372336
• H Acceptors: 21
• H Donor: 23
• LogD (pH = 5.5): -7.9905834
• LogD (pH = 7.4): -5.890713
• Log P: 1.8233017
• Molar Refractivity: 542.9171 cm^3
• Polarizability: 207.79225 Å^3
• Polar Surface Area: 620.71 Å^2
• Rotatable Bonds: 48
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - I0144

Biochem/physiol Actions
Exhibits potent antimicrobial activity in vitro against bacteria and fungi.