(3S,6S,9S,15S,18S,21S,24R,29R,32S,35S,38S,41S)-24-amino-3,35-bis(4-aminobutyl)-32-(hydroxymethyl)-21-[(4-hydroxyphenyl)methyl]-15,18,38-trimethyl-6-(2-methylpropyl)-2,5,8,14,17,20,23,31,34,37,40-undecaoxo-26,27-dithia-1,4,7,13,16,19,22,30,33,36,39-undecaazatricyclo[39.3.0.09,13]tetratetracontane-29-carboxylic acid

• ChemBase ID: 154825
• Molecular Formular: C55H88N14O15S2
• Molecular Mass: 1249.50202
• Monoisotopic Mass: 1248.59950019
• SMILES: C[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N1)CCCCN)CC(C)C)C)C)Cc1ccc(cc1)O)N)C(=O)O)CO)CCCCN
• Canonical SMILES: NCCCC[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC1=O)CO)C(=O)O)N)Cc1ccc(cc1)O)C
• InChI: InChI=1S/C55H88N14O15S2/c1-29(2)24-38-49(77)63-37(13-7-9-21-57)54(82)69-23-11-14-42(69)51(79)60-31(4)45(73)62-36(12-6-8-20-56)47(75)66-40(26-70)50(78)67-41(55(83)84)28-86-85-27-35(58)46(74)64-39(25-33-16-18-34(71)19-17-33)48(76)59-30(3)44(72)61-32(5)53(81)68-22-10-15-43(68)52(80)65-38/h16-19,29-32,35-43,70-71H,6-15,20-28,56-58H2,1-5H3,(H,59,76)(H,60,79)(H,61,72)(H,62,73)(H,63,77)(H,64,74)(H,65,80)(H,66,75)(H,67,78)(H,83,84)/t30-,31-,32-,35-,36-,37-,38-,39-,40-,41-,42-,43-/m0/s1
• InChIKey: MPUVBZQBFGGAAS-XHGDPFBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9S,15S,18S,21S,24R,29R,32S,35S,38S,41S)-24-amino-3,35-bis(4-aminobutyl)-32-(hydroxymethyl)-21-[(4-hydroxyphenyl)methyl]-15,18,38-trimethyl-6-(2-methylpropyl)-2,5,8,14,17,20,23,31,34,37,40-undecaoxo-26,27-dithia-1,4,7,13,16,19,22,30,33,36,39-undecaazatricyclo[39.3.0.0^9,^1^3]tetratetracontane-29-carboxylic acid
• IUPAC Traditional name: (3S,6S,9S,15S,18S,21S,24R,29R,32S,35S,38S,41S)-24-amino-3,35-bis(4-aminobutyl)-32-(hydroxymethyl)-21-[(4-hydroxyphenyl)methyl]-15,18,38-trimethyl-6-(2-methylpropyl)-2,5,8,14,17,20,23,31,34,37,40-undecaoxo-26,27-dithia-1,4,7,13,16,19,22,30,33,36,39-undecaazatricyclo[39.3.0.0^9,^1^3]tetratetracontane-29-carboxylic acid
• Synonyms: H-Cys-Tyr-Ala-Ala-Pro-Leu-Lys-Pro-Ala-Lys-Ser-Cys-OH trifluoroacetate salt; JB-1 trifluoroacetate salt; L-Cysteinyl-L-tyrosyl-L-alanyl-L-alanyl-L-prolyl-L-leucyl-L-lysyl-L-prolyl-L-alanyl-L-lysyl-L-seryl-L-Cysteine, cyclic (1-12)-disulfide trifluoroacetate salt; JB1 trifluoroacetate salt

Database IDs

• CAS Number: 147819-32-7(freebase)
• MDL Number: MFCD00237120
• PubChem SID: 162248963
• PubChem CID: 71311995

CALCULATED PROPERTIES

• Acid pKa: 3.0944
• H Acceptors: 18
• H Donor: 15
• LogD (pH = 5.5): -12.24215
• LogD (pH = 7.4): -9.962798
• Log P: -8.054036
• Molar Refractivity: 316.4657 cm^3
• Polarizability: 124.511345 Å^3
• Polar Surface Area: 458.34 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: film

Safety Information

• Storage Condition: desiccated
• German water hazard class: nwg
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C55H88N14O15S2 · xC2HF3O2

DETAILS

Sigma Aldrich - J3705

Biochem/physiol Actions
JB1 is an IGF-I peptide analog; IGF-1 receptor antagonist. IGF-1, once known as somatomedin C, is involved in a multitude of activites including promoting growth and development, particularly neural development, and involved in the growth and proliferation in a variety of human cancers. JB1 is a 12-amino acid cyclic peptide, an IGF-1 analog, used by researchers in a variety of fields to inhibit IGF activity by inhibiting binding of IGF-1 to its receptor.