(3S)-3-{[(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}-3-[(2S)-2-[(2S,3R)-2-{2-[(2S)-2-aminopropanamido]acetamido}-3-hydroxybutanamido]propanamido]propanoic acid

• ChemBase ID: 131291
• Molecular Formular: C62H84N14O17S2
• Molecular Mass: 1361.54396
• Monoisotopic Mass: 1360.5580293
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](C)C(=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)CNC(=O)[C@H](C)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](NC(=O)[C@H]([C@H](O)C)NC(=O)CNC(=O)[C@@H](N)C)C)CC(=O)O)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C62H84N14O17S2/c1-31(2)50(62(92)93)76-60(90)47-30-95-94-29-46(73-58(88)45(26-49(80)81)69-53(83)33(4)67-61(91)51(34(5)77)75-48(79)28-66-52(82)32(3)64)59(89)71-42(23-35-13-7-6-8-14-35)55(85)72-44(25-37-27-65-40-16-10-9-15-39(37)40)57(87)68-41(17-11-12-22-63)54(84)70-43(56(86)74-47)24-36-18-20-38(78)21-19-36/h6-10,13-16,18-21,27,31-34,41-47,50-51,65,77-78H,11-12,17,22-26,28-30,63-64H2,1-5H3,(H,66,82)(H,67,91)(H,68,87)(H,69,83)(H,70,84)(H,71,89)(H,72,85)(H,73,88)(H,74,86)(H,75,79)(H,76,90)(H,80,81)(H,92,93)/t32-,33-,34+,41-,42-,43-,44-,45-,46-,47-,50-,51-/m0/s1
• InChIKey: YNQKMDDGZLLKHF-SYGGZGJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(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}-3-[(2S)-2-[(2S,3R)-2-{2-[(2S)-2-aminopropanamido]acetamido}-3-hydroxybutanamido]propanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(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}-3-[(2S)-2-[(2S,3R)-2-{2-[(2S)-2-aminopropanamido]acetamido}-3-hydroxybutanamido]propanamido]propanoic acid
• Synonyms: Urotensin II mouse

Database IDs

• MDL Number: MFCD00076818
• PubChem SID: 162225569
• PubChem CID: 16150418

CALCULATED PROPERTIES

• Acid pKa: 3.0671084
• H Acceptors: 19
• H Donor: 18
• LogD (pH = 5.5): -7.5455937
• LogD (pH = 7.4): -7.6195035
• Log P: -7.5443196
• Molar Refractivity: 345.3821 cm^3
• Polarizability: 136.38763 Å^3
• Polar Surface Area: 502.99 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: mouse ... Uts2(24111)

Product Information

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

DETAILS

Sigma Aldrich - U7382

Amino Acid Sequence
pGlu-His-Gly-Ala-Ala-Pro-Glu-Cys-Phe-Trp-Lys-Tyr-Cys-Ile [Disulfide Bridge: 8-13]
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.