(2S)-1-{5-carbamimidamido-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-5-yl)-2-[(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; acetic acid

• ChemBase ID: 172270
• Molecular Formular: C61H88N16O14
• Molecular Mass: 1269.45022
• Monoisotopic Mass: 1268.66659158
• SMILES: c1ccc2c(c1)[nH]cc2C[C@H](NC(=O)[C@@H](NC(=O)C1NC(=O)CC1)Cc1[nH]cnc1)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)NC(C(=O)N1CCC[C@H]1C(=O)NCC)CCCNC(=N)N)CC(C)C)CC(C)C)Cc1ccc(cc1)O)CO.CC(=O)O
• Canonical SMILES: CC(=O)O.CCNC(=O)[C@@H]1CCCN1C(=O)C(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](Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1)CO)CC(C)C)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C59H84N16O12.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t40?,41?,42-,43+,44+,45+,46+,47+,48+;/m1./s1
• InChIKey: RGLRXNKKBLIBQS-WFAPNXKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-{5-carbamimidamido-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-5-yl)-2-[(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; acetic acid
• IUPAC Traditional name: (2S)-1-{5-carbamimidamido-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(3H-imidazol-4-yl)-2-[(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; acetic acid
• Synonyms: 6-D-Leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamideluteinizing Hormone-Releasing Factor Acetate(Pig); A 43818; Abbott 43818; Leuprorelin Acetate; Lupron; Procren Depot; Procrin; Prostap; TAP 144; TAP 144SR; Leuprolide Acetate

Database IDs

• CAS Number: 74381-53-6
• PubChem SID: 164228180
• PubChem CID: 71749769

CALCULATED PROPERTIES

• Acid pKa: 9.489494
• H Acceptors: 16
• H Donor: 16
• LogD (pH = 5.5): -5.1849093
• LogD (pH = 7.4): -4.437766
• Log P: -2.7400792
• Molar Refractivity: 327.8074 cm^3
• Polarizability: 123.91096 Å^3
• Polar Surface Area: 429.04 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 150-155°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L330600

Synthetic nonapeptide agonist analog of LH-RH. Antineoplastic (hormonal).

REFERENCES

• Vilchez-Martinez, J.A., et al.: Biochem. Biophys. Res. Commun., 59, 1226 (1974)
• Sennello, L.T., et al.: J. Pharm. Sci., et al.: 75, 158 (1974)
• Wheeler, J.M., et al.: Am.J. Obstet. Gynecol., 167, 1367 (1974)
• Eri, L.M., et al.: J. Urol., 150, 359 (1974)