(3S)-3-{[(1S)-1-[({[(1S,2S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}ethyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}ethyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}-2-methylbutyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}-3-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-carbamoylpropanamido]propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]propanoic acid

• ChemBase ID: 154612
• Molecular Formular: C114H174N34O31
• Molecular Mass: 2516.81056
• Monoisotopic Mass: 2515.30842496
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N)NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](Cc1ccccc1)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CC(C)C)C)CCCNC(=N)N)Cc1nc[nH]c1)CCC(=O)N)CCC(=O)N)Cc1ccc(cc1)O)CCC(=O)N)C)CO)CC(C)C)NC(=O)[C@H]([C@H](CC)C)NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)N)CC(=O)N)C)Cc1ccccc1)CC(=O)O
• InChI: InChI=1S/C114H174N34O31/c1-12-60(8)93(146-90(157)54-128-111(177)92(59(6)7)147-109(175)81(50-91(158)159)143-108(174)78(46-65-25-17-14-18-26-65)144-110(176)83-29-22-42-148(83)113(179)63(11)132-105(171)80(49-87(120)154)139-97(163)69(116)45-64-23-15-13-16-24-64)112(178)137-71(27-19-20-40-115)101(167)140-76(44-58(4)5)106(172)145-82(55-149)99(165)127-52-88(155)130-61(9)95(161)134-72(34-37-84(117)151)103(169)141-77(47-66-30-32-68(150)33-31-66)107(173)136-73(35-38-85(118)152)102(168)135-74(36-39-86(119)153)104(170)142-79(48-67-51-124-56-129-67)98(164)126-53-89(156)133-70(28-21-41-125-114(122)123)100(166)131-62(10)96(162)138-75(94(121)160)43-57(2)3/h13-18,23-26,30-33,51,56-63,69-83,92-93,149-150H,12,19-22,27-29,34-50,52-55,115-116H2,1-11H3,(H2,117,151)(H2,118,152)(H2,119,153)(H2,120,154)(H2,121,160)(H,124,129)(H,126,164)(H,127,165)(H,128,177)(H,130,155)(H,131,166)(H,132,171)(H,133,156)(H,134,161)(H,135,168)(H,136,173)(H,137,178)(H,138,162)(H,139,163)(H,140,167)(H,141,169)(H,142,170)(H,143,174)(H,144,176)(H,145,172)(H,146,157)(H,147,175)(H,158,159)(H4,122,123,125)/t60-,61-,62-,63-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,92-,93-/m0/s1
• InChIKey: OJSXICLEROKMBP-FFUDWAICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-[({[(1S,2S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}ethyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}ethyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}-2-methylbutyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}-3-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-carbamoylpropanamido]propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-[({[(1S,2S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}ethyl]carbamoyl}butyl]carbamoyl}methyl)carbamoyl]-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}ethyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}-2-methylbutyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}-3-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-carbamoylpropanamido]propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]propanoic acid
• Synonyms: Obestatin mouse, rat

Database IDs

• CAS Number: 869705-22-6
• MDL Number: MFCD08458632
• PubChem SID: 162248750
• PubChem CID: 71311910

CALCULATED PROPERTIES

• Acid pKa: 3.7246118
• H Acceptors: 37
• H Donor: 35
• LogD (pH = 5.5): -20.929743
• LogD (pH = 7.4): -18.104916
• Log P: -16.0007
• Molar Refractivity: 643.8555 cm^3
• Polarizability: 247.75702 Å^3
• Polar Surface Area: 1067.24 Å^2
• Rotatable Bonds: 81
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: deionized water: soluble0.5-1 mg/mL
• Apperance: white lyophilized powder

Safety Information

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

Pharmacology Properties

• Gene Information: mouse ... Ghrl(58991)rat ... Ghrl(59301)

Product Information

• Biological Source: from synthetic
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C114H174N34O31

DETAILS

Sigma Aldrich - O0266

Amino Acid Sequence
Phe-Asn-Ala-Pro-Phe-Asp-Val-Gly-Ile-Lys-Leu-Ser-Gly-Ala-Gln-Tyr-Gln-Gln-His-Gly-Arg-Ala-Leu-NH2
Physical form
Lyophilized from 0.1% aqueous trifluoroacetate (TFA).
Biochem/physiol Actions
Obestatin, an obesity peptide, along with Ghrelin peptides are derived from the same prepropeptide, Ghrelin. In contrast to Ghrelin, Obestatin suppresses food intake, body weight gain, and gastrointestinal motility in rodents.1