2-[(3R,6S,9R,12R,17aS)-9-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-1,4,7,10,13-pentaoxo-3-(propan-2-yl)-hexadecahydro-1H-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-12-yl]acetic acid

• ChemBase ID: 126220
• Molecular Formular: C31H42N6O7
• Molecular Mass: 610.70118
• Monoisotopic Mass: 610.31149771
• SMILES: CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(=O)N1)C(C)C)CC(=O)O)Cc1c[nH]c2ccccc12
• Canonical SMILES: CC(C[C@@H]1NC(=O)[C@H](NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](NC1=O)Cc1c[nH]c2c1cccc2)CC(=O)O)C(C)C)C
• InChI: InChI=1S/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23+,24-,26+/m0/s1
• InChIKey: VYCMAAOURFJIHD-PJNXIOHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3R,6S,9R,12R,17aS)-9-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-1,4,7,10,13-pentaoxo-3-(propan-2-yl)-hexadecahydro-1H-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-12-yl]acetic acid
• IUPAC Traditional name: [(3R,6S,9R,12R,17aS)-9-(1H-indol-3-ylmethyl)-3-isopropyl-6-(2-methylpropyl)-1,4,7,10,13-pentaoxo-dodecahydropyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-12-yl]acetic acid
• Synonyms: Cyclo(D-trp-D-asp-L-pro-D-val-L-leu); BQ-123; BQ-123

Database IDs

• CAS Number: 136553-81-6
• MDL Number: MFCD00133204
• PubChem SID: 24891595; 162220560
• PubChem CID: 443289
• CHEMBL: 1269102
• IUPHAR ligand ID: 1003
• Wikipedia Title: BQ-123

CALCULATED PROPERTIES

• Acid pKa: 4.044945
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -0.6214315
• LogD (pH = 7.4): -2.2879717
• Log P: 0.8449524
• Molar Refractivity: 158.5862 cm^3
• Polarizability: 63.051422 Å^3
• Polar Surface Area: 189.8 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: lyophilized powder

Safety Information

• German water hazard class: 3
• Safety Statements: S22 S24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... EDNRA(1909), EDNRB(1910)rat ... Ednra(24326), Ednrb(50672)

Product Information

• Purity: ≥99%

DETAILS

Sigma Aldrich - B150

Amino Acid Sequence
cyclo-Asp-Pro-Val-Leu-Trp
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Selective ETA endothelin receptor antagonist.

Sigma Aldrich - C1306

Amino Acid Sequence
cyclo-Asp-Pro-Val-Leu-Trp
Biochem/physiol Actions
Selective endothelin A (ETA) antagonist