(2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]pentanediamide

• ChemBase ID: 153591
• Molecular Formular: C65H92N20O15S
• Molecular Mass: 1425.61598
• Monoisotopic Mass: 1424.67717334
• 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](CCC(=O)N)NC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2
• Canonical SMILES: 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](NC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)CCC(=O)N)Cc1nc[nH]c1
• InChI: InChI=1S/C65H92N20O15S/c1-34(2)23-43(58(94)78-42(11-7-21-71-64(68)69)63(99)85-22-8-12-49(85)62(98)73-29-52(67)89)77-54(91)30-74-56(92)44(24-35-15-17-38(87)18-16-35)79-61(97)47(31-86)82-59(95)45(25-36-27-72-40-10-4-3-9-39(36)40)80-60(96)46(26-37-28-70-33-75-37)81-57(93)41(19-20-51(66)88)76-53(90)14-6-5-13-50-55-48(32-101-50)83-65(100)84-55/h3-4,9-10,15-18,27-28,33-34,41-50,55,72,86-87H,5-8,11-14,19-26,29-32H2,1-2H3,(H2,66,88)(H2,67,89)(H,70,75)(H,73,98)(H,74,92)(H,76,90)(H,77,91)(H,78,94)(H,79,97)(H,80,96)(H,81,93)(H,82,95)(H4,68,69,71)(H2,83,84,100)/t41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,55-/m0/s1
• InChIKey: KZAFISRCTGJDLA-PVPGZCQVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]pentanediamide
• IUPAC Traditional name: (2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-(carbamoylmethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]pentanediamide
• Synonyms: [Biotinyl-Gln1]-LH-RH

Database IDs

• CAS Number: 218433-98-8
• MDL Number: MFCD00168140
• PubChem SID: 162247730
• PubChem CID: 71311686

CALCULATED PROPERTIES

• Acid pKa: 9.497697
• H Acceptors: 19
• H Donor: 20
• LogD (pH = 5.5): -9.097907
• LogD (pH = 7.4): -8.088392
• Log P: -6.3840666
• Molar Refractivity: 374.1055 cm^3
• Polarizability: 142.22882 Å^3
• Polar Surface Area: 556.35 Å^2
• Rotatable Bonds: 40
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

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

Product Information

• Purity: >97% (HPLC)
• Empirical Formula (Hill Notation): C65H92N20O15S

DETAILS

Sigma Aldrich - L4288

Amino Acid Sequence
Biotinyl-Gln-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2
Biochem/physiol Actions
LH-RH derivative used in the functional analysis of LH-RH receptor ligand binding.