(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,49S,52R)-52-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-49-benzyl-28,37-bis[(2S)-butan-2-yl]-31,40-bis(3-carbamimidamidopropyl)-19-(2-carbamoylethyl)-34-(carboxymethyl)-16-(hydroxymethyl)-22-methyl-10-(2-methylpropyl)-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-hexadecaazacyclotripentacontan-4-yl]formamido}-3-carbamoylpropanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(4-hydroxyphenyl)propanoic acid

• ChemBase ID: 132046
• Molecular Formular: C113H177N39O35S2
• Molecular Mass: 2705.98478
• Monoisotopic Mass: 2704.27107056
• 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)NCC(=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)[C@@H](C)CC)CCCNC(=N)N)Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)N)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)O)CC(C)C)CO)CCC(=O)N)C
• Canonical SMILES: CC[C@@H]([C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)CNC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CSSC[C@H](NC(=O)CNC(=O)[C@@H](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](NC1=O)CC(=O)O)CCCNC(=N)N)[C@H](CC)C)C)CCC(=O)N)CO)CC(C)C)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)O)Cc1ccc(cc1)O)CCCNC(=N)N)Cc1ccccc1)CO)CC(=O)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCNC(=N)N)N)CO)CO)C
• InChI: InChI=1S/C113H177N39O35S2/c1-8-56(5)88-107(184)133-46-83(161)134-58(7)90(167)138-67(32-33-80(115)158)96(173)147-74(49-153)94(171)132-47-85(163)136-68(38-55(3)4)92(169)131-48-86(164)137-78(105(182)143-71(42-81(116)159)100(177)148-76(51-155)102(179)142-70(40-60-22-14-11-15-23-60)99(176)139-65(26-18-36-127-112(121)122)95(172)145-73(109(186)187)41-61-28-30-62(157)31-29-61)53-188-189-54-79(150-104(181)77(52-156)149-103(180)75(50-154)146-91(168)63(114)24-16-34-125-110(117)118)106(183)141-69(39-59-20-12-10-13-21-59)93(170)130-44-82(160)129-45-84(162)135-64(25-17-35-126-111(119)120)97(174)152-89(57(6)9-2)108(185)144-72(43-87(165)166)101(178)140-66(98(175)151-88)27-19-37-128-113(123)124/h10-15,20-23,28-31,55-58,63-79,88-89,153-157H,8-9,16-19,24-27,32-54,114H2,1-7H3,(H2,115,158)(H2,116,159)(H,129,160)(H,130,170)(H,131,169)(H,132,171)(H,133,184)(H,134,161)(H,135,162)(H,136,163)(H,137,164)(H,138,167)(H,139,176)(H,140,178)(H,141,183)(H,142,179)(H,143,182)(H,144,185)(H,145,172)(H,146,168)(H,147,173)(H,148,177)(H,149,180)(H,150,181)(H,151,175)(H,152,174)(H,165,166)(H,186,187)(H4,117,118,125)(H4,119,120,126)(H4,121,122,127)(H4,123,124,128)/t56-,57-,58-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,88-,89-/m0/s1
• InChIKey: ASJKJMQNGMTJDL-PSTTWCJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,49S,52R)-52-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-49-benzyl-28,37-bis[(2S)-butan-2-yl]-31,40-bis(3-carbamimidamidopropyl)-19-(2-carbamoylethyl)-34-(carboxymethyl)-16-(hydroxymethyl)-22-methyl-10-(2-methylpropyl)-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-hexadecaazacyclotripentacontan-4-yl]formamido}-3-carbamoylpropanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(4-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,49S,52R)-52-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-49-benzyl-28,37-bis[(2S)-butan-2-yl]-31,40-bis(3-carbamimidamidopropyl)-19-(2-carbamoylethyl)-34-(carboxymethyl)-16-(hydroxymethyl)-22-methyl-10-(2-methylpropyl)-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-hexadecaazacyclotripentacontan-4-yl]formamido}-3-carbamoylpropanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-(4-hydroxyphenyl)propanoic acid
• Synonyms: Auriculin® B; rANF 4-28; Atrial Natriuretic Peptide fragment 4-28 rat

Database IDs

• CAS Number: 90052-57-6
• MDL Number: MFCD00076239
• PubChem SID: 162226323
• PubChem CID: 16138068

CALCULATED PROPERTIES

• Acid pKa: 3.1849766
• H Acceptors: 48
• H Donor: 46
• LogD (pH = 5.5): -29.341328
• LogD (pH = 7.4): -27.643505
• Log P: -25.001825
• Molar Refractivity: 710.1309 cm^3
• Polarizability: 260.22888 Å^3
• Polar Surface Area: 1233.95 Å^2
• Rotatable Bonds: 56
• 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 ... Nppa(24602)

DETAILS

Sigma Aldrich - A2677

Biochem/physiol Actions
Atrial natriuretic peptide (ANP) is synthesized in myoendocrine cells of the heart from which it is released into the circulation. It exerts natriuretic, diuretic, and vasodilatory effects through stimulation of guanylate cyclase-linked NPR-A receptors. It plays an important role in blood volume and blood pressure homeostasis.
法律信息
Auriculin is a registered trademark of California Biotechnology, Inc.