(2S)-2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[2-(2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]acetamido}acetamido)acetamido]-3-hydroxybutanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]hexanamido]-4-(methylsulfanyl)butanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]acetamido}-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]butanediamide

• ChemBase ID: 155263
• Molecular Formular: C130H204N38O31S2
• Molecular Mass: 2859.37676
• Monoisotopic Mass: 2857.49961394
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N)NC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)N)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=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)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCSC)CC(C)C)Cc1nc[nH]c1)C(C)C)C)Cc1c[nH]c2c1cccc2)Cc1nc[nH]c1)CC(=O)N)CCCNC(=N)N)Cc1ccc(cc1)O)CCSC)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@H](O)C)NC(=O)CNC(=O)CNC(=O)CNC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)N)CC(C)C)C)CC(C)C
• InChI: InChI=1S/C130H204N38O31S2/c1-65(2)47-86(115(185)152-82(108(134)178)38-45-200-17)156-116(186)89(52-77-56-137-63-146-77)150-101(176)62-145-123(193)104(69(9)10)163-110(180)72(14)148-114(184)88(51-76-55-140-81-28-20-19-27-80(76)81)157-117(187)90(53-78-57-138-64-147-78)158-118(188)91(54-97(132)172)151-100(175)61-144-111(181)83(30-23-41-139-130(135)136)154-121(191)95-32-25-43-167(95)128(198)93(50-75-34-36-79(171)37-35-75)160-113(183)85(39-46-201-18)153-112(182)84(29-21-22-40-131)155-125(195)107(74(16)170)165-119(189)87(48-66(3)4)159-124(194)105(70(11)12)164-126(196)106(73(15)169)162-102(177)60-142-98(173)58-141-99(174)59-143-109(179)71(13)149-120(190)94-31-24-42-166(94)127(197)92(49-67(5)6)161-122(192)96-33-26-44-168(96)129(199)103(133)68(7)8/h19-20,27-28,34-37,55-57,63-74,82-96,103-107,140,169-171H,21-26,29-33,38-54,58-62,131,133H2,1-18H3,(H2,132,172)(H2,134,178)(H,137,146)(H,138,147)(H,141,174)(H,142,173)(H,143,179)(H,144,181)(H,145,193)(H,148,184)(H,149,190)(H,150,176)(H,151,175)(H,152,185)(H,153,182)(H,154,191)(H,155,195)(H,156,186)(H,157,187)(H,158,188)(H,159,194)(H,160,183)(H,161,192)(H,162,177)(H,163,180)(H,164,196)(H,165,189)(H4,135,136,139)/t71-,72-,73+,74+,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,103-,104-,105-,106-,107-/m0/s1
• InChIKey: PUBCCFNQJQKCNC-XKNFJVFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[2-(2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]acetamido}acetamido)acetamido]-3-hydroxybutanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]hexanamido]-4-(methylsulfanyl)butanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]acetamido}-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]butanediamide
• IUPAC Traditional name: (2S)-2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[2-(2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]acetamido}acetamido)acetamido]-3-hydroxybutanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]hexanamido]-4-(methylsulfanyl)butanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]acetamido}-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]butanediamide
• Synonyms: GRP; Val-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr-Val-Leu-Thr-Lys-Met-Tyr-Pro-Arg-Gly-Asn-His-Trp-Ala-Val-Gly-His-Leu-Met-NH2; Gastrin Releasing Peptide human

Database IDs

• CAS Number: 93755-85-2
• MDL Number: MFCD00133362
• PubChem SID: 162249401
• PubChem CID: 71312111

CALCULATED PROPERTIES

• Acid pKa: 9.445099
• H Acceptors: 38
• H Donor: 36
• LogD (pH = 5.5): -20.68027
• LogD (pH = 7.4): -16.847519
• Log P: -11.660154
• Molar Refractivity: 741.6527 cm^3
• Polarizability: 286.91504 Å^3
• Polar Surface Area: 1064.19 Å^2
• Rotatable Bonds: 85
• 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 ... GRP(2922)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ≥65%
• Empirical Formula (Hill Notation): C130H204N38O31S2

DETAILS

Sigma Aldrich - G8022

Amino Acid Sequence
Val-Pro-Leu-Pro-Ala-Gly-Gly-Gly-Thr-Val-Leu-Thr-Lys-Met-Tyr-Pro-Arg-Gly-Asn-His-Trp-Ala-Val-Gly-His-Leu-Met-NH2
Linkage
Mammalian equivalent of bombesin that is found in the central nervous system and gastrointestinal tract. It inhibits food intake. It is produced by and is mitogenic for several tumor cell lines.