(4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,43S,49S,52R)-52-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-(2-aminoacetamido)-4-methylpentanamido]-3-hydroxypropanamido]hexanamido]acetamido}-40-(4-aminobutyl)-49-benzyl-28-[(2S)-butan-2-yl]-31-(3-carbamimidamidopropyl)-34-(carboxymethyl)-16,22-bis(hydroxymethyl)-10,37,43-tris(2-methylpropyl)-19-[2-(methylsulfanyl)ethyl]-6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51-hexadecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50-hexadecaazacyclotripentacontane-4-carboxylic acid

• ChemBase ID: 133940
• Molecular Formular: C93H157N27O28S3
• Molecular Mass: 2197.60078
• Monoisotopic Mass: 2196.08535052
• SMILES: CC[C@H](C)[C@H]1C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CSSC[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)N1)CCCNC(=N)N)CC(=O)O)CC(C)C)CCCCN)CC(C)C)Cc1ccccc1)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)CN)C(=O)O)CC(C)C)CO)CCSC)CO
• Canonical SMILES: NCCCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CSSC[C@H](NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CC(C)C)CC(=O)O)CCCNC(=N)N)[C@H](CC)C)CO)CCSC)CO)C(=O)O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CN)CC(C)C)CO)CCCCN
• InChI: InChI=1S/C93H157N27O28S3/c1-12-52(10)76-91(146)104-42-72(127)108-65(44-122)88(143)114-57(26-30-149-11)82(137)118-64(43-121)80(135)103-39-70(125)106-58(31-48(2)3)78(133)101-41-74(129)110-68(92(147)148)47-151-150-46-67(109-73(128)40-100-77(132)54(23-16-18-27-94)111-89(144)66(45-123)119-85(140)59(32-49(4)5)105-69(124)37-96)90(145)116-62(35-53-21-14-13-15-22-53)79(134)102-38-71(126)107-60(33-50(6)7)84(139)112-55(24-17-19-28-95)81(136)115-61(34-51(8)9)86(141)117-63(36-75(130)131)87(142)113-56(83(138)120-76)25-20-29-99-93(97)98/h13-15,21-22,48-52,54-68,76,121-123H,12,16-20,23-47,94-96H2,1-11H3,(H,100,132)(H,101,133)(H,102,134)(H,103,135)(H,104,146)(H,105,124)(H,106,125)(H,107,126)(H,108,127)(H,109,128)(H,110,129)(H,111,144)(H,112,139)(H,113,142)(H,114,143)(H,115,136)(H,116,145)(H,117,141)(H,118,137)(H,119,140)(H,120,138)(H,130,131)(H,147,148)(H4,97,98,99)/t52-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,76-/m0/s1
• InChIKey: UHSBKBYWHCBDCJ-DYGWFTAGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,43S,49S,52R)-52-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-(2-aminoacetamido)-4-methylpentanamido]-3-hydroxypropanamido]hexanamido]acetamido}-40-(4-aminobutyl)-49-benzyl-28-[(2S)-butan-2-yl]-31-(3-carbamimidamidopropyl)-34-(carboxymethyl)-16,22-bis(hydroxymethyl)-10,37,43-tris(2-methylpropyl)-19-[2-(methylsulfanyl)ethyl]-6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51-hexadecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50-hexadecaazacyclotripentacontane-4-carboxylic acid
• IUPAC Traditional name: (4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,43S,49S,52R)-52-{2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-(2-aminoacetamido)-4-methylpentanamido]-3-hydroxypropanamido]hexanamido]acetamido}-40-(4-aminobutyl)-49-benzyl-28-[(2S)-butan-2-yl]-31-(3-carbamimidamidopropyl)-34-(carboxymethyl)-16,22-bis(hydroxymethyl)-10,37,43-tris(2-methylpropyl)-19-[2-(methylsulfanyl)ethyl]-6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51-hexadecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50-hexadecaazacyclotripentacontane-4-carboxylic acid
• Synonyms: CNP; Natriuretic Peptide, C-Type

Database IDs

• CAS Number: 127869-51-6
• MDL Number: MFCD00080348
• PubChem SID: 162228217
• PubChem CID: 16179407

CALCULATED PROPERTIES

• Acid pKa: 2.9001875
• H Acceptors: 34
• H Donor: 32
• LogD (pH = 5.5): -20.964418
• LogD (pH = 7.4): -18.645645
• Log P: -16.011309
• Molar Refractivity: 559.3719 cm^3
• Polarizability: 215.71477 Å^3
• Polar Surface Area: 886.35 Å^2
• Rotatable Bonds: 43
• 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 ... NPPC(4880)

Product Information

• Purity: ≥95% (HPLC)
• Compostion: Peptide content, ≥65%

DETAILS

Sigma Aldrich - N8768

Amino Acid Sequence
Gly-Leu-Ser-Lys-Gly-Cys-Phe-Gly-Leu-Lys-Leu-Asp-Arg-Ile-Gly-Ser-Met-Ser-Gly-Leu-Gly-Cys [Disulfide Bridge: 6-22]
Biochem/physiol Actions
C-type natriuretic peptide is produced in the hypothalamus, anterior pituitary, and most major endocrine glands. It has potent venodilatory and coronary vasodilatory effects, but minimal effects on renal function.