(2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(1-benzyl-1H-imidazol-4-yl)-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]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanoyl]-N-ethylpyrrolidine-2-carboxamide

• ChemBase ID: 130514
• Molecular Formular: C66H86N18O12
• Molecular Mass: 1323.50244
• Monoisotopic Mass: 1322.66726028
• SMILES: CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1cn(Cc2ccccc2)cn1)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1)Cc1c[nH]c2ccccc12
• Canonical SMILES: CCNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](Cc1ncn(c1)Cc1ccccc1)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)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)/t47-,48-,49-,50-,51-,52-,53+,54-,55-/m0/s1
• InChIKey: HHXHVIJIIXKSOE-QILQGKCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(1-benzyl-1H-imidazol-4-yl)-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]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanoyl]-N-ethylpyrrolidine-2-carboxamide
• IUPAC Traditional name: histrelina
• Synonyms: Histrelin

Database IDs

• CAS Number: 76712-82-8
• PubChem SID: 162224793
• PubChem CID: 25077993
• ATC CODE: L02AE05
• CHEMBL: 1201255
• Chemspider ID: 10482012
• KEGG ID: D02369
• Unique Ingredient Identifier: H50H3S3W74
• Wikipedia Title: Histrelin
• Medline Plus: a601146

CALCULATED PROPERTIES

• Acid pKa: 9.490034
• H Acceptors: 17
• H Donor: 16
• LogD (pH = 5.5): -5.5210433
• LogD (pH = 7.4): -3.8571594
• Log P: -2.1384223
• Molar Refractivity: 360.0734 cm^3
• Polarizability: 136.12662 Å^3
• Polar Surface Area: 446.86 Å^2
• Rotatable Bonds: 34
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: Subcutaneous implant
• Bioavailability: 92%
• Excretion: Undetermined
• Half Life: 4 hours
• Metabolism: Hepatic
• Protein Bound: 70%
• Legal Status: Rx-only (US)
• Pregnancy Category: X (US)