(4S)-4-amino-4-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(4R,7S,10S,13S,16S,19R)-10-(4-aminobutyl)-16-benzyl-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-7-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]carbamoyl}-2-carboxyethyl]carbamoyl}pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]carbamoyl}butanoic acid

• ChemBase ID: 132778
• Molecular Formular: C64H85N13O18S2
• Molecular Mass: 1388.566
• Monoisotopic Mass: 1387.55769495
• SMILES: C[C@H]([C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1ccccc1)Cc1c[nH]c2c1cccc2)CCCCN)Cc1ccc(cc1)O)C(=O)N[C@@H](C(C)C)C(=O)O)NC(=O)[C@H](CCC(=O)O)N)O
• Canonical SMILES: NCCCC[C@@H]1NC(=O)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC1=O)Cc1ccc(cc1)O)C(=O)N[C@H](C(=O)O)C(C)C)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](O)C)NC(=O)[C@H](CCC(=O)O)N)CC(=O)O)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C64H85N13O18S2/c1-33(2)52(64(94)95)75-61(91)48-32-97-96-31-47(73-59(89)46(29-51(82)83)72-62(92)49-17-11-25-77(49)63(93)53(34(3)78)76-54(84)40(66)22-23-50(80)81)60(90)70-43(26-35-12-5-4-6-13-35)56(86)71-45(28-37-30-67-41-15-8-7-14-39(37)41)58(88)68-42(16-9-10-24-65)55(85)69-44(57(87)74-48)27-36-18-20-38(79)21-19-36/h4-8,12-15,18-21,30,33-34,40,42-49,52-53,67,78-79H,9-11,16-17,22-29,31-32,65-66H2,1-3H3,(H,68,88)(H,69,85)(H,70,90)(H,71,86)(H,72,92)(H,73,89)(H,74,87)(H,75,91)(H,76,84)(H,80,81)(H,82,83)(H,94,95)/t34-,40+,42+,43+,44+,45+,46+,47+,48+,49+,52+,53+/m1/s1
• InChIKey: HFNHAPQMXICKCF-USJMABIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-amino-4-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(4R,7S,10S,13S,16S,19R)-10-(4-aminobutyl)-16-benzyl-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-7-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]carbamoyl}-2-carboxyethyl]carbamoyl}pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-amino-4-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(4R,7S,10S,13S,16S,19R)-10-(4-aminobutyl)-16-benzyl-4-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-7-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]carbamoyl}-2-carboxyethyl]carbamoyl}pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]carbamoyl}butanoic acid
• Synonyms: Urotensin II human

Database IDs

• MDL Number: MFCD04115626
• PubChem SID: 162227055
• PubChem CID: 46225600

CALCULATED PROPERTIES

• Acid pKa: 2.9760048
• H Acceptors: 20
• H Donor: 17
• LogD (pH = 5.5): -8.055638
• LogD (pH = 7.4): -9.7642565
• Log P: -6.8739634
• Molar Refractivity: 351.0581 cm^3
• Polarizability: 138.66672 Å^3
• Polar Surface Area: 502.4 Å^2
• Rotatable Bonds: 27
• 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 ... UTS2(10911)

Product Information

• Purity: ≥97% (HPLC)
• Biological Source: synthetic

DETAILS

Sigma Aldrich - U7257

Amino Acid Sequence
Glu-Thr-Pro-Asp-Cys-Phe-Trp-Lys-Tyr-Cys-Val [Disulfide Bridge: 5-10]
Biochem/physiol Actions
A neuroendocrine peptide of the CRF family that was originally isolated from fish brain but is also found in mammalian brain and spinal motor neurons. It is a potent vasoconstrictor. It may be a mediator of stress-induced anorexia.