37-{2-[2-(6-amino-2-{2-[2-(2-{[1-(2-{2-[2-({1-[2-(2-{2-[2-(2-amino-3-hydroxypropanamido)propanamido]-3-carbamoylpropanamido}-3-hydroxypropanamido)-3-carbamoylpropanoyl]pyrrolidin-2-yl}formamido)propanamido]-4-(methylsulfanyl)butanamido}propanoyl)pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido)-4-carboxybutanamido]-5-carbamimidamidopentanamido}hexanamido)propanamido]acetamido}-19,34-bis(4-aminobutyl)-13,25,28-tribenzyl-31-(carbamoylmethyl)-10,16-bis(1-hydroxyethyl)-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontane-4-carboxylic acid

• ChemBase ID: 103829
• Molecular Formular: C137H207N41O39S3
• Molecular Mass: 3148.55578
• Monoisotopic Mass: 3146.46369901
• SMILES: NCCCCC(NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C1CCCN1C(=O)C(C)NC(=O)C(CCSC)NC(=O)C(C)NC(=O)C1CCCN1C(=O)C(CC(=O)N)NC(=O)C(CO)NC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(N)CO)C(=O)NC(C)C(=O)NCC(=O)NC1CSSCC(NC(=O)C(CO)NC(=O)C(NC(=O)C(Cc2ccccc2)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(NC(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccccc2)NC(=O)C(CC(=O)N)NC(=O)C(CCCCN)NC1=O)Cc1c[nH]c2ccccc12)C(C)O)C(C)O)C(=O)O
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NCC(=O)NC1CSSCC(NC(=O)C(CO)NC(=O)C(NC(=O)C(Cc2ccccc2)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCCCN)CC(=O)N)Cc1ccccc1)Cc1ccccc1)Cc1c[nH]c2c1cccc2)CCCCN)C(O)C)C(O)C)C(=O)O)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1CCCN1C(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1CCCN1C(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(CO)N)C)CC(=O)N)CO)CC(=O)N)C)CCSC)C)CCCNC(=N)N)CCC(=O)O)CCCNC(=N)N
• InChI: InChI=1S/C137H207N41O39S3/c1-69(154-113(194)82(37-19-22-47-138)159-115(196)85(40-25-50-149-136(145)146)160-118(199)87(44-45-106(188)189)163-116(197)86(41-26-51-150-137(147)148)164-130(211)101-43-27-52-177(101)133(214)72(4)156-114(195)88(46-54-218-7)158-110(191)71(3)155-129(210)100-42-28-53-178(100)134(215)95(61-104(144)186)171-126(207)96(65-180)172-124(205)93(59-102(142)184)165-111(192)70(2)153-112(193)80(141)64-179)109(190)152-63-105(187)157-98-67-219-220-68-99(135(216)217)174-127(208)97(66-181)173-132(213)108(74(6)183)176-125(206)91(57-77-33-15-10-16-34-77)170-131(212)107(73(5)182)175-119(200)84(39-21-24-49-140)161-122(203)92(58-78-62-151-81-36-18-17-35-79(78)81)168-121(202)90(56-76-31-13-9-14-32-76)166-120(201)89(55-75-29-11-8-12-30-75)167-123(204)94(60-103(143)185)169-117(198)83(162-128(98)209)38-20-23-48-139/h8-18,29-36,62,69-74,80,82-101,107-108,151,179-183H,19-28,37-61,63-68,138-141H2,1-7H3,(H2,142,184)(H2,143,185)(H2,144,186)(H,152,190)(H,153,193)(H,154,194)(H,155,210)(H,156,195)(H,157,187)(H,158,191)(H,159,196)(H,160,199)(H,161,203)(H,162,209)(H,163,197)(H,164,211)(H,165,192)(H,166,201)(H,167,204)(H,168,202)(H,169,198)(H,170,212)(H,171,207)(H,172,205)(H,173,213)(H,174,208)(H,175,200)(H,176,206)(H,188,189)(H,216,217)(H4,145,146,149)(H4,147,148,150)
• InChIKey: GGYTXJNZMFRSLX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 37-{2-[2-(6-amino-2-{2-[2-(2-{[1-(2-{2-[2-({1-[2-(2-{2-[2-(2-amino-3-hydroxypropanamido)propanamido]-3-carbamoylpropanamido}-3-hydroxypropanamido)-3-carbamoylpropanoyl]pyrrolidin-2-yl}formamido)propanamido]-4-(methylsulfanyl)butanamido}propanoyl)pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido)-4-carboxybutanamido]-5-carbamimidamidopentanamido}hexanamido)propanamido]acetamido}-19,34-bis(4-aminobutyl)-13,25,28-tribenzyl-31-(carbamoylmethyl)-10,16-bis(1-hydroxyethyl)-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontane-4-carboxylic acid
• IUPAC Traditional name: 37-{2-[2-(6-amino-2-{2-[2-(2-{[1-(2-{2-[2-({1-[2-(2-{2-[2-(2-amino-3-hydroxypropanamido)propanamido]-3-carbamoylpropanamido}-3-hydroxypropanamido)-3-carbamoylpropanoyl]pyrrolidin-2-yl}formamido)propanamido]-4-(methylsulfanyl)butanamido}propanoyl)pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido)-4-carboxybutanamido]-5-carbamimidamidopentanamido}hexanamido)propanamido]acetamido}-19,34-bis(4-aminobutyl)-13,25,28-tribenzyl-31-(carbamoylmethyl)-10,16-bis(1-hydroxyethyl)-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24,27,30,33,36-undecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35-undecaazacyclooctatriacontane-4-carboxylic acid
• Synonyms: Somatostatin 28; Prosomatostatin; Ser-Ala-Asn-Ser-Asn-Pro-Ala-Met-Ala-Pro-Arg-Glu-Arg-Lys-Ala-Gly-Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys; SOMATOSTATIN-28

Database IDs

• CAS Number: 73032-94-7
• MDL Number: MFCD00076772
• PubChem SID: 162103305; 24899687
• PubChem CID: 16132331

CALCULATED PROPERTIES

• Acid pKa: 2.807595
• H Acceptors: 49
• H Donor: 46
• LogD (pH = 5.5): -33.621742
• LogD (pH = 7.4): -30.723179
• Log P: -22.819685
• Molar Refractivity: 808.6473 cm^3
• Polarizability: 309.3214 Å^3
• Polar Surface Area: 1316.81 Å^2
• Rotatable Bonds: 76
• 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 ... SST(6750)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 02152999

Contains disulfide bond between Cys17 and Cys28.

Sigma Aldrich - S6135

Amino Acid Sequence
Ser-Ala-Asn-Ser-Asn-Pro-Ala-Met-Ala-Pro-Arg-Glu-Arg-Lys-Ala-Gly-Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys [Disulfide Bridge: 17-28]
Biochem/physiol Actions
Mediates inhibition of peptide YY secretion from rat intestinal cultures.

REFERENCES

• Pradyrol L., et al., FEBS Lett., 109: 55, (1980).
• Schally, A.V., et al., Proc. Natl. Acad. Sci. USA, 77: 4489 (1980).