(2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-{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]acetamido}-4-methylpentanamide; bis(acetic acid)

• ChemBase ID: 155154
• Molecular Formular: C59H83N17O17
• Molecular Mass: 1302.39402
• Monoisotopic Mass: 1301.61528428
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)CNC(=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.CC(=O)O
• Canonical SMILES: CC(=O)O.CC(=O)O.OC[C@@H](C(=O)N[C@H](C(=O)NCC(=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)Cc1ccc(cc1)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H]1CCC(=O)N1)Cc1nc[nH]c1
• InChI: InChI=1S/C55H75N17O13.2C2H4O2/c1-29(2)19-38(49(80)67-37(9-5-17-60-55(57)58)54(85)72-18-6-10-43(72)53(84)62-25-44(56)75)66-46(77)26-63-47(78)39(20-30-11-13-33(74)14-12-30)68-52(83)42(27-73)71-50(81)40(21-31-23-61-35-8-4-3-7-34(31)35)69-51(82)41(22-32-24-59-28-64-32)70-48(79)36-15-16-45(76)65-36;2*1-2(3)4/h3-4,7-8,11-14,23-24,28-29,36-43,61,73-74H,5-6,9-10,15-22,25-27H2,1-2H3,(H2,56,75)(H,59,64)(H,62,84)(H,63,78)(H,65,76)(H,66,77)(H,67,80)(H,68,83)(H,69,82)(H,70,79)(H,71,81)(H4,57,58,60);2*1H3,(H,3,4)/t36-,37-,38-,39-,40-,41-,42-,43-;;/m0../s1
• InChIKey: QOVPLTBEZAJSHY-VIRDRFNDSA-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-{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]acetamido}-4-methylpentanamide; bis(acetic acid)
• IUPAC Traditional name: (2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-(carbamoylmethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-{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]acetamido}-4-methylpentanamide; bis(acetic acid)
• Synonyms: Gonadoliberin; Gonadotropin releasing hormone; LH-RH; Luteinizing hormone releasing hormone human acetate salt

Database IDs

• CAS Number: 71447-49-9
• EC Number: 232-895-0
• MDL Number: MFCD00133489
• PubChem SID: 162249292
• PubChem CID: 56841073

CALCULATED PROPERTIES

• Acid pKa: 9.489069
• H Acceptors: 17
• H Donor: 17
• LogD (pH = 5.5): -8.610211
• LogD (pH = 7.4): -7.595745
• Log P: -5.909876
• Molar Refractivity: 312.2324 cm^3
• Polarizability: 117.86168 Å^3
• Polar Surface Area: 472.13 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble25 mg/mL, clear, faintly yellow
• Apperance: powder

Safety Information

• RTECS: OK6470000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 2; 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; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... GNRH1(2796)

Product Information

• Purity: ≥80% peptide basis; ≥98% (HPLC); ≥98.0% (HPLC)
• Impurities: ≤10% water; ≤12% acetate
• Mol. Weight: Mr 1182.33
• Empirical Formula (Hill Notation): C55H75N17O13

DETAILS

Sigma Aldrich - L7134

Amino Acid Sequence
Glp-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2
Components
pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2
Other Notes
free peptide
Biochem/physiol Actions
Hypothalamic peptide that stimulates release of gonadotrophins from anterior pituitary, thus regulating reproductive functions.

Sigma Aldrich - 62690

Amino Acid Sequence
Glp-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2
Components
pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2
Other Notes
free peptide
The principal regulator of the Ca2+-dependent release of gonadotropins, LH and follicle-stimulating hormone1
Biochem/physiol Actions
Hypothalamic peptide that stimulates release of gonadotrophins from anterior pituitary, thus regulating reproductive functions.