(2S)-2,6-diamino-N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S,2S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S,3S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}butyl]carbamoyl}-2-hydroxyethyl]hexanamide

• ChemBase ID: 153981
• Molecular Formular: C65H118N18O15
• Molecular Mass: 1391.74402
• Monoisotopic Mass: 1390.90240517
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=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)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CC(C)C)CC(C)C)CO)C(C)C)[C@H](CC)C)C)C(C)C)[C@H](CC)C)CCCNC(=N)N)CO)N
• InChI: InChI=1S/C65H118N18O15/c1-14-37(11)50(80-55(89)41(22-18-26-71-65(69)70)73-57(91)44(31-84)76-54(88)40(67)21-16-17-25-66)62(96)79-49(36(9)10)63(97)82-27-19-23-46(82)59(93)72-39(13)53(87)81-51(38(12)15-2)64(98)83-28-20-24-47(83)60(94)78-48(35(7)8)61(95)77-45(32-85)58(92)75-43(30-34(5)6)56(90)74-42(52(68)86)29-33(3)4/h33-51,84-85H,14-32,66-67H2,1-13H3,(H2,68,86)(H,72,93)(H,73,91)(H,74,90)(H,75,92)(H,76,88)(H,77,95)(H,78,94)(H,79,96)(H,80,89)(H,81,87)(H4,69,70,71)/t37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-/m0/s1
• InChIKey: WXRGGPLCKMBEAF-OLAWGTLASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2,6-diamino-N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S,2S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S,3S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}butyl]carbamoyl}-2-hydroxyethyl]hexanamide
• IUPAC Traditional name: (2S)-2,6-diamino-N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S,2S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S,3S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}butyl]carbamoyl}-2-hydroxyethyl]hexanamide
• Synonyms: KSRIVPAIPVSLL-NH2; IDR-1; Innate defense regulator peptide-1; KSRIVPAIPVSLL; [H]-Lys-Ser-Arg-Ile-Val-Pro-Ala-Ile-Pro-Val-Ser-Leu-Leu-[NH2]; H-Lys-Ser-Arg-Ile-Val-Pro-Ala-Ile-Pro-Val-Ser-Leu-Leu-NH2

Database IDs

• PubChem SID: 162248120
• PubChem CID: 16129238

CALCULATED PROPERTIES

• Acid pKa: 11.417336
• H Acceptors: 20
• H Donor: 18
• LogD (pH = 5.5): -11.399344
• LogD (pH = 7.4): -9.288428
• Log P: -4.235277
• Molar Refractivity: 371.6235 cm^3
• Polarizability: 142.29832 Å^3
• Polar Surface Area: 529.11 Å^2
• Rotatable Bonds: 43
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble >1 mg/mL
• Apperance: lyophilized powder (provided as TFA salt)

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: ≥95% (HPLC)
• Compostion: Protein content, ~91%
• Empirical Formula (Hill Notation): C65H118N18O15

DETAILS

Sigma Aldrich - I6409

Amino Acid Sequence
Lys-Ser-Arg-Ile-Val-Pro-Ala-Ile-Pro-Val-Ser-Leu-Leu-NH2
Biochem/physiol Actions
IDR-1 is an anti-infective peptide that acts on the host to stimulate the innate immune response. IDR-1 is believed to act by enhancing monocyte chemokines, while reducing pro-inflammatory cytokines (decreased TNF and IL-6 and increased IL-10).