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

• ChemBase ID: 132643
• Molecular Formular: C59H84N16O12
• Molecular Mass: 1209.39826
• Monoisotopic Mass: 1208.64546221
• SMILES: CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1
• Canonical SMILES: CCNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1)CO)CC(C)C)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44-,45-,46-,47-,48-/m0/s1
• InChIKey: GFIJNRVAKGFPGQ-LIJARHBVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-4-methylpentanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide
• IUPAC Traditional name: leuprorelin
• Synonyms: Leuprorelin; des-Gly10-[D-Leu6]-LH-RH ethylamide; Leuprolide acetate salt

Database IDs

• CAS Number: 74381-53-6
• MDL Number: MFCD00167544
• PubChem SID: 162226920; 24896252
• PubChem CID: 657181

CALCULATED PROPERTIES

• Acid pKa: 9.4892025
• H Acceptors: 16
• H Donor: 16
• LogD (pH = 5.5): -5.1015697
• LogD (pH = 7.4): -4.0871816
• Log P: -2.4015148
• Molar Refractivity: 327.2417 cm^3
• Polarizability: 123.91099 Å^3
• Polar Surface Area: 429.04 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: OH6390000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... GNRHR(2798)rat ... Gnrhr(81668)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - L0399

Amino Acid Sequence
Glp-His-Trp-Ser-Tyr-Leu-Leu-Arg-Pro-NHEt
Biochem/physiol Actions
Luteinizing hormone releasing hormone (LH-RH) agonist.