1-(2-{2-[3-(1-benzyl-1H-imidazol-4-yl)-2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamido}-5-carbamimidamidopentanoyl)-N-ethylpyrrolidine-2-carboxamide

• ChemBase ID: 133628
• Molecular Formular: C66H86N18O12
• Molecular Mass: 1323.50244
• Monoisotopic Mass: 1322.66726028
• SMILES: CCNC(=O)C1CCCN1C(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(Cc1cn(cn1)Cc1ccccc1)NC(=O)C(Cc1ccc(cc1)O)NC(=O)C(CO)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1
• Canonical SMILES: CCNC(=O)C1CCCN1C(=O)C(NC(=O)C(NC(=O)C(Cc1ncn(c1)Cc1ccccc1)NC(=O)C(Cc1ccc(cc1)O)NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1)CO)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C66H86N18O12/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71)
• InChIKey: HHXHVIJIIXKSOE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-{2-[3-(1-benzyl-1H-imidazol-4-yl)-2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamido}-5-carbamimidamidopentanoyl)-N-ethylpyrrolidine-2-carboxamide
• IUPAC Traditional name: 1-(2-{2-[3-(1-benzylimidazol-4-yl)-2-[2-(3-hydroxy-2-{2-[3-(3H-imidazol-4-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamido}-5-carbamimidamidopentanoyl)-N-ethylpyrrolidine-2-carboxamide
• Synonyms: Histrelin; [des-Gly10, D-His(Bzl)6]-LH-RH ethylamide

Database IDs

• CAS Number: 76712-82-8
• MDL Number: MFCD00133494
• PubChem SID: 24896325; 162227905
• PubChem CID: 25078009

CALCULATED PROPERTIES

• Acid pKa: 9.490408
• H Acceptors: 17
• H Donor: 16
• LogD (pH = 5.5): -5.6043873
• LogD (pH = 7.4): -4.207813
• Log P: -2.476892
• Molar Refractivity: 360.6391 cm^3
• Polarizability: 136.12659 Å^3
• Polar Surface Area: 446.86 Å^2
• Rotatable Bonds: 34
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• RTECS: OK6370800
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... GNRH1(2796), GNRHR(2798)mouse ... GNRH1(14714), GNRHR(14715)rat ... GNRH1(25194), GNRHR(81668)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - L2761

Amino Acid Sequence
Glp-His-Trp-Ser-Tyr-His(Bzl)-Leu-Arg-Pro-NHEt
Biochem/physiol Actions
Potent LH-RH agonist; inhibits actions of sex steroids on the male and female reproductive organs.
Features and Benefits
Has greater lipophilicity than other LH-RH agonists, but retains high water solubility