(2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-5-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamide acetic acid hydrate

• ChemBase ID: 133618
• Molecular Formular: C58H83N17O16
• Molecular Mass: 1274.38392
• Monoisotopic Mass: 1273.62036966
• SMILES: C[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1.CC(=O)O.O
• Canonical SMILES: CC(=O)O.OC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)CCCNC(=N)N)CC(C)C)C)Cc1ccc(cc1)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H]1CCC(=O)N1)Cc1[nH]cnc1.O
• InChI: InChI=1S/C56H77N17O13.C2H4O2.H2O/c1-29(2)20-39(50(81)67-38(10-6-18-61-56(58)59)55(86)73-19-7-11-44(73)54(85)63-26-45(57)76)68-47(78)30(3)65-49(80)40(21-31-12-14-34(75)15-13-31)69-53(84)43(27-74)72-51(82)41(22-32-24-62-36-9-5-4-8-35(32)36)70-52(83)42(23-33-25-60-28-64-33)71-48(79)37-16-17-46(77)66-37;1-2(3)4;/h4-5,8-9,12-15,24-25,28-30,37-44,62,74-75H,6-7,10-11,16-23,26-27H2,1-3H3,(H2,57,76)(H,60,64)(H,63,85)(H,65,80)(H,66,77)(H,67,81)(H,68,78)(H,69,84)(H,70,83)(H,71,79)(H,72,82)(H4,58,59,61);1H3,(H,3,4);1H2/t30-,37+,38+,39+,40+,41+,42+,43+,44+;;/m1../s1
• InChIKey: KGUIXKYKIZMKMT-JGUOWLKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-5-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamide acetic acid hydrate
• IUPAC Traditional name: (2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-(carbamoylmethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(3H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamide acetic acid hydrate
• Synonyms: (D-Ala-6) Luteinizing Hormone Releasing Hormone; [D-Ala6]-LH-RH acetate salt hydrate

Database IDs

• PubChem SID: 24896296; 162227895
• PubChem CID: 16219557

CALCULATED PROPERTIES

• Acid pKa: 9.489627
• H Acceptors: 17
• H Donor: 17
• LogD (pH = 5.5): -8.124793
• LogD (pH = 7.4): -7.377733
• Log P: -5.679402
• Molar Refractivity: 317.292 cm^3
• Polarizability: 119.69103 Å^3
• Polar Surface Area: 472.13 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: OK6400000
• 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)

Product Information

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

DETAILS

Sigma Aldrich - L1898

Amino Acid Sequence
Glp-His-Trp-Ser-Tyr-Ala-Leu-Arg-Pro-Gly-NH2
Biochem/physiol Actions
Potent LH-RH agonist.