1-[(2S)-5-carbamimidamido-2-[(2S)-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]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide; acetic acid

• ChemBase ID: 166252
• Molecular Formular: C66H87N17O14
• Molecular Mass: 1342.50248
• Monoisotopic Mass: 1341.66184055
• SMILES: c12c(c[nH]c1cccc2)C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCC(=O)N1)Cc1cnc[nH]1)Cc1c2c([nH]c1)cccc2)CO)Cc1ccc(cc1)O)C(=O)N[C@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCCC1C(=O)NCC)CC(C)C.C(=O)(O)C
• Canonical SMILES: CC(=O)O.CCNC(=O)C1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)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)[C@@H]1CCC(=O)N1)CO)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C64H83N17O12.C2H4O2/c1-4-68-62(92)53-16-10-24-81(53)63(93)46(15-9-23-69-64(65)66)74-56(86)47(25-35(2)3)75-58(88)49(27-37-30-70-43-13-7-5-11-41(37)43)77-57(87)48(26-36-17-19-40(83)20-18-36)76-61(91)52(33-82)80-59(89)50(28-38-31-71-44-14-8-6-12-42(38)44)78-60(90)51(29-39-32-67-34-72-39)79-55(85)45-21-22-54(84)73-45;1-2(3)4/h5-8,11-14,17-20,30-32,34-35,45-53,70-71,82-83H,4,9-10,15-16,21-29,33H2,1-3H3,(H,67,72)(H,68,92)(H,73,84)(H,74,86)(H,75,88)(H,76,91)(H,77,87)(H,78,90)(H,79,85)(H,80,89)(H4,65,66,69);1H3,(H,3,4)/t45-,46-,47-,48-,49+,50-,51-,52-,53?;/m0./s1
• InChIKey: LYCYLGFSIXIXAB-SBFVSPNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S)-5-carbamimidamido-2-[(2S)-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]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide; acetic acid
• IUPAC Traditional name: 1-[(2S)-5-carbamimidamido-2-[(2S)-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]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide; acetic acid
• Synonyms: D-Trp6-Pro9-N-ethylamide-LH-RH Acetate; H 4065 Acetate; PTL 3001 Acetate; Somagard Acetate; [D-Trp6,Pro9-NHEt]LH-RH; [D-Trp6,des-Gly-NH210]-LH-RH Ethylamide Acetate; [de-Gly10,D-Trp6,Pro-NHEt]-LH-RH Acetate; Ovuplant; Deslorelin Acetate; 6-D-Tryptophan-9-(N-ethyl-L-prolinamide)-1-9-luteinizing Hormone-releasing Factor (Swine) Monoacetate; Bachem 9022 Acetate; D-Trp LHRH-PEA Acetate

Database IDs

• CAS Number: 82318-06-7
• PubChem SID: 162260385
• PubChem CID: 71315648

CALCULATED PROPERTIES

• Acid pKa: 9.489732
• H Acceptors: 16
• H Donor: 17
• LogD (pH = 5.5): -4.6839356
• LogD (pH = 7.4): -3.9369307
• Log P: -2.2388346
• Molar Refractivity: 349.8393 cm^3
• Polarizability: 133.11292 Å^3
• Polar Surface Area: 444.83 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290290

An injectable gonadotropin-releasing hormone (GnRH) super-agonist (also known as an LHRH agonist). Used in treatment of precocious puberty and commonly used in veterinary medicine to induce ovulation in mares.

REFERENCES

• Linde, R. et al.: Engl. J. Med., 305, 663 (1981)
• Manasco, P.K. et al.: J. Pediatr., 115, 105 (1981)
• Johnson, C.A. et al.: J. Anim. Sci., 81, 1300 (1981)
• Farquhar, V.J. et al.: J. Am. Vet. Med. Assoc., 218, 749 (1981)