(3S)-3-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-[(2S)-2-[(2R)-2-acetamido-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]propanoic acid

• ChemBase ID: 132132
• Molecular Formular: C46H62N8O10
• Molecular Mass: 887.03208
• Monoisotopic Mass: 886.45889022
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)C
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)[C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)C)CC(C)C)CC(=O)O)C
• InChI: InChI=1S/C46H62N8O10/c1-8-25(5)39(44(61)52-37(46(63)64)20-29-23-48-33-17-13-11-15-31(29)33)54-45(62)40(26(6)9-2)53-43(60)36(21-38(56)57)51-41(58)34(18-24(3)4)50-42(59)35(49-27(7)55)19-28-22-47-32-16-12-10-14-30(28)32/h10-17,22-26,34-37,39-40,47-48H,8-9,18-21H2,1-7H3,(H,49,55)(H,50,59)(H,51,58)(H,52,61)(H,53,60)(H,54,62)(H,56,57)(H,63,64)/t25-,26-,34-,35+,36-,37-,39-,40-/m0/s1
• InChIKey: ZYNCQGUPXUKGPO-CCAWOAKWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-[(2S)-2-[(2R)-2-acetamido-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-[(2S)-2-[(2R)-2-acetamido-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]propanoic acid
• Synonyms: N-Acetyl-[D-Trp16]-Endothelin 1 fragment 16-21

Database IDs

• CAS Number: 143037-33-6
• MDL Number: MFCD00236979
• PubChem SID: 24894644; 162226409
• PubChem CID: 9897583

CALCULATED PROPERTIES

• Acid pKa: 3.783801
• H Acceptors: 10
• H Donor: 10
• LogD (pH = 5.5): 0.5235444
• LogD (pH = 7.4): -2.839306
• Log P: 3.3441432
• Molar Refractivity: 234.7413 cm^3
• Polarizability: 93.88579 Å^3
• Polar Surface Area: 280.78 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... EDN1(1906)rat ... Ednra(24326), Ednrb(50672), Gnrhr(81668)

Product Information

• Compostion: Dye content, ≥95% HPLC

DETAILS

Sigma Aldrich - E7394

Amino Acid Sequence
Ac-D-Trp-Leu-Asp-Ile-Ile-Trp
Biochem/physiol Actions
ETA antagonist; inhibits ET-1 stimulated arachidonic acid release in rabbit vascular smooth muscle cells.