(4S)-4-{[(4R,7S,10S,13S,16S,19R)-10-(4-aminobutyl)-16-benzyl-4-{[(1S,2S)-1-carboxy-2-methylbutyl]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}-4-{[(2S)-1-[(2S)-2-[(2S,3R)-3-hydroxy-2-{2-[(2S)-3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]acetamido}butanamido]propanoyl]pyrrolidin-2-yl]formamido}butanoic acid

• ChemBase ID: 133317
• Molecular Formular: C77H102N18O20S2
• Molecular Mass: 1663.87238
• Monoisotopic Mass: 1662.69591975
• SMILES: CC[C@H](C)[C@@H](C(=O)O)NC(=O)[C@@H]1CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)Cc1ccc(cc1)O)CCCCN)Cc1c[nH]c2c1cccc2)Cc1ccccc1)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)CNC(=O)[C@H](Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1
• 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@H](CC)C)C(=O)O)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)CNC(=O)[C@@H](NC(=O)C1CCC(=O)N1)Cc1[nH]cnc1)C)CCC(=O)O)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C77H102N18O20S2/c1-5-40(2)63(77(114)115)94-73(110)58-38-117-116-37-57(72(109)88-53(30-43-14-7-6-8-15-43)69(106)89-55(32-45-34-80-49-17-10-9-16-48(45)49)71(108)85-50(18-11-12-28-78)66(103)87-54(70(107)92-58)31-44-20-22-47(97)23-21-44)91-68(105)52(25-27-62(100)101)86-74(111)59-19-13-29-95(59)76(113)41(3)83-75(112)64(42(4)96)93-61(99)36-81-65(102)56(33-46-35-79-39-82-46)90-67(104)51-24-26-60(98)84-51/h6-10,14-17,20-23,34-35,39-42,50-59,63-64,80,96-97H,5,11-13,18-19,24-33,36-38,78H2,1-4H3,(H,79,82)(H,81,102)(H,83,112)(H,84,98)(H,85,108)(H,86,111)(H,87,103)(H,88,109)(H,89,106)(H,90,104)(H,91,105)(H,92,107)(H,93,99)(H,94,110)(H,100,101)(H,114,115)/t40-,41-,42+,50-,51?,52-,53-,54-,55-,56-,57-,58-,59-,63-,64-/m0/s1
• InChIKey: BOBVDMGRLAZVCI-BGYIBPDASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(4R,7S,10S,13S,16S,19R)-10-(4-aminobutyl)-16-benzyl-4-{[(1S,2S)-1-carboxy-2-methylbutyl]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}-4-{[(2S)-1-[(2S)-2-[(2S,3R)-3-hydroxy-2-{2-[(2S)-3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]acetamido}butanamido]propanoyl]pyrrolidin-2-yl]formamido}butanoic acid
• IUPAC Traditional name: (4S)-4-{[(4R,7S,10S,13S,16S,19R)-10-(4-aminobutyl)-16-benzyl-4-{[(1S,2S)-1-carboxy-2-methylbutyl]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}-4-{[(2S)-1-[(2S)-2-[(2S,3R)-3-hydroxy-2-{2-[(2S)-3-(3H-imidazol-4-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]acetamido}butanamido]propanoyl]pyrrolidin-2-yl]formamido}butanoic acid
• Synonyms: Urotensin II rat

Database IDs

• PubChem SID: 162227594
• PubChem CID: 71308656

CALCULATED PROPERTIES

• Acid pKa: 3.2355967
• H Acceptors: 22
• H Donor: 20
• LogD (pH = 5.5): -8.607123
• LogD (pH = 7.4): -9.729308
• Log P: -8.172529
• Molar Refractivity: 422.1742 cm^3
• Polarizability: 165.64854 Å^3
• Polar Surface Area: 584.16 Å^2
• Rotatable Bonds: 34
• 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: rat ... Uts2(29180)

Product Information

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

DETAILS

Sigma Aldrich - U7507

Amino Acid Sequence
Glp-His-Gly-Thr-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.