(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]propanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide acetic acid hydrate

• ChemBase ID: 133177
• Molecular Formular: C58H84N16O15
• Molecular Mass: 1245.38576
• Monoisotopic Mass: 1244.63020607
• SMILES: CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](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.CC(=O)O.O
• Canonical SMILES: CC(=O)O.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)C)CC(C)C)CCCNC(=N)N.O
• InChI: InChI=1S/C56H78N16O12.C2H4O2.H2O/c1-5-60-54(83)45-13-9-21-72(45)55(84)39(12-8-20-61-56(57)58)66-50(79)40(22-30(2)3)67-47(76)31(4)64-49(78)41(23-32-14-16-35(74)17-15-32)68-53(82)44(28-73)71-51(80)42(24-33-26-62-37-11-7-6-10-36(33)37)69-52(81)43(25-34-27-59-29-63-34)70-48(77)38-18-19-46(75)65-38;1-2(3)4;/h6-7,10-11,14-17,26-27,29-31,38-45,62,73-74H,5,8-9,12-13,18-25,28H2,1-4H3,(H,59,63)(H,60,83)(H,64,78)(H,65,75)(H,66,79)(H,67,76)(H,68,82)(H,69,81)(H,70,77)(H,71,80)(H4,57,58,61);1H3,(H,3,4);1H2/t31-,38+,39+,40+,41+,42+,43+,44+,45+;;/m1../s1
• InChIKey: YEEHIOYEWOESQR-PFHUABGLSA-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]propanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide acetic acid hydrate
• IUPAC Traditional 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]propanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide acetic acid hydrate
• Synonyms: [des-Gly10, D-Ala6]-LH-RH ethylamide acetate salt hydrate

Database IDs

• MDL Number: MFCD11046043
• PubChem SID: 162227454
• PubChem CID: 71308644

CALCULATED PROPERTIES

• Acid pKa: 9.489245
• H Acceptors: 16
• H Donor: 16
• LogD (pH = 5.5): -6.3556824
• LogD (pH = 7.4): -5.3413186
• Log P: -3.6551735
• Molar Refractivity: 313.5681 cm^3
• Polarizability: 118.41496 Å^3
• Polar Surface Area: 429.04 Å^2
• Rotatable Bonds: 30
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60
• Safety Statements: 53-45
• 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: mouse ... GNRH1(2796), GNRHR(2798)rat ... GNRH1(14714), GNRHR(14715)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - L4513

Amino Acid Sequence
Glp-His-Trp-Ser-Tyr-Ala-Leu-Arg-Pro-NHEt
Biochem/physiol Actions
Potent LH-RH agonist in rats and mice; reversibly delays sexual maturation in rats, stimulates spawning activity in fish.