(2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(tert-butoxy)-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]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanoyl]-N-ethylpyrrolidine-2-carboxamide; acetic acid

• ChemBase ID: 163110
• Molecular Formular: C62H90N16O15
• Molecular Mass: 1299.4762
• Monoisotopic Mass: 1298.67715626
• SMILES: N1(CCC[C@H]1C(=O)NCC)C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1[nH]cnc1)NC(=O)C1NC(=O)CC1.CC(=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](Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1)CO)COC(C)(C)C)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C60H86N16O13.C2H4O2/c1-7-64-57(87)48-15-11-23-76(48)58(88)41(14-10-22-65-59(61)62)69-51(81)42(24-33(2)3)70-56(86)47(31-89-60(4,5)6)75-52(82)43(25-34-16-18-37(78)19-17-34)71-55(85)46(30-77)74-53(83)44(26-35-28-66-39-13-9-8-12-38(35)39)72-54(84)45(27-36-29-63-32-67-36)73-50(80)40-20-21-49(79)68-40;1-2(3)4/h8-9,12-13,16-19,28-29,32-33,40-48,66,77-78H,7,10-11,14-15,20-27,30-31H2,1-6H3,(H,63,67)(H,64,87)(H,68,79)(H,69,81)(H,70,86)(H,71,85)(H,72,84)(H,73,80)(H,74,83)(H,75,82)(H4,61,62,65);1H3,(H,3,4)/t40?,41-,42-,43-,44-,45-,46-,47+,48-;/m0./s1
• InChIKey: PYMDEDHDQYLBRT-YOGFSURDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(tert-butoxy)-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]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanoyl]-N-ethylpyrrolidine-2-carboxamide; acetic acid
• IUPAC Traditional name: (2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(tert-butoxy)-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]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanoyl]-N-ethylpyrrolidine-2-carboxamide; acetic acid
• Synonyms: 6-[O-(1,1-Dimethylethyl)-D-serine]-9-(N-ethyl-L-prolinamide)-1-9-luteinizing Hormone-releasing Factor Monoacetate; Estomal; Suprafact; Suprecur; Supremon; Buserelin Acetate

Database IDs

• CAS Number: 68630-75-1
• PubChem SID: 162257245
• PubChem CID: 71314307

CALCULATED PROPERTIES

• Acid pKa: 9.488896
• H Acceptors: 17
• H Donor: 16
• LogD (pH = 5.5): -5.788839
• LogD (pH = 7.4): -5.041358
• Log P: -3.3443122
• Molar Refractivity: 334.2343 cm^3
• Polarizability: 126.46944 Å^3
• Polar Surface Area: 438.27 Å^2
• Rotatable Bonds: 33
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 186-188°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B689740

Gondadotropin-releasing hormone agonist, used to treat hormone-responsive cancers such as prostate and breast cancer. Synthetic nonapeptide agonist analog of LH-RH. Antineolpastic (hormonal).

REFERENCES

• Lam, P., et al.: Gynecol. Endocrinol., 24, 674 (2008)
• Chi, K., et al.: J. Urol., 180, 565 (2008)
• Menchaca, A., et al.: Theriogenol., 72, 477 (2008)
• Harada, T., et al.: Fertility and Sterility, 91, 675 (2008)