(4S)-4-amino-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid

• ChemBase ID: 155653
• Molecular Formular: C25H31N7O8
• Molecular Mass: 557.55574
• Monoisotopic Mass: 557.22341099
• SMILES: c1ccc2c(c1)c(c[nH]2)C[C@@H](C(=O)N[C@@H](CO)C(=O)O)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](CCC(=O)O)N
• Canonical SMILES: OC[C@@H](C(=O)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@H](CCC(=O)O)N)Cc1nc[nH]c1
• InChI: InChI=1S/C25H31N7O8/c26-16(5-6-21(34)35)22(36)30-19(8-14-10-27-12-29-14)24(38)31-18(23(37)32-20(11-33)25(39)40)7-13-9-28-17-4-2-1-3-15(13)17/h1-4,9-10,12,16,18-20,28,33H,5-8,11,26H2,(H,27,29)(H,30,36)(H,31,38)(H,32,37)(H,34,35)(H,39,40)/t16-,18-,19-,20-/m0/s1
• InChIKey: FMJXVANOHHICFP-LEAZDLGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-amino-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-amino-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid
• Synonyms: LH-RH Fragment 1-4

Database IDs

• MDL Number: MFCD03452958
• PubChem SID: 162249791
• PubChem CID: 71312188

CALCULATED PROPERTIES

• Acid pKa: 3.178545
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -6.945441
• LogD (pH = 7.4): -7.809727
• Log P: -6.6538577
• Molar Refractivity: 137.4251 cm^3
• Polarizability: 54.670662 Å^3
• Polar Surface Area: 252.62 Å^2
• Rotatable Bonds: 15
• 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), GNRHR(2798)mouse ... GNRH1(14714), GNRHR(14715)rat ... GNRH1(25194), GNRHR(81668)

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C25H29N7O7

DETAILS

Sigma Aldrich - L6038

Amino Acid Sequence
Glp-His-Trp-Ser