(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-amino-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-carbamimidamidopentanoic acid

• ChemBase ID: 132465
• Molecular Formular: C98H156N34O32S2
• Molecular Mass: 2386.62584
• Monoisotopic Mass: 2385.106631
• 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)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)O)CC(C)C)CO)CCC(=O)N)C
• Canonical SMILES: OC[C@@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@@H](NC1=O)Cc1ccccc1)CCCNC(=N)N)[C@H](CC)C)CC(=O)O)CCCNC(=N)N)[C@H](CC)C)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)Cc1ccccc1)CO)CC(=O)N)NC(=O)[C@H](CO)N
• InChI: InChI=1S/C98H156N34O32S2/c1-8-48(5)76-93(161)115-38-71(140)116-50(7)78(146)120-56(26-27-68(100)137)83(151)128-63(42-134)82(150)114-39-73(142)118-58(31-47(3)4)80(148)113-40-74(143)119-66(91(159)125-61(34-69(101)138)87(155)129-65(44-136)89(157)124-60(33-52-21-14-11-15-22-52)86(154)122-57(95(163)164)25-18-30-110-98(106)107)45-165-166-46-67(130-90(158)64(43-135)127-79(147)53(99)41-133)92(160)123-59(32-51-19-12-10-13-20-51)81(149)112-36-70(139)111-37-72(141)117-54(23-16-28-108-96(102)103)84(152)132-77(49(6)9-2)94(162)126-62(35-75(144)145)88(156)121-55(85(153)131-76)24-17-29-109-97(104)105/h10-15,19-22,47-50,53-67,76-77,133-136H,8-9,16-18,23-46,99H2,1-7H3,(H2,100,137)(H2,101,138)(H,111,139)(H,112,149)(H,113,148)(H,114,150)(H,115,161)(H,116,140)(H,117,141)(H,118,142)(H,119,143)(H,120,146)(H,121,156)(H,122,154)(H,123,160)(H,124,157)(H,125,159)(H,126,162)(H,127,147)(H,128,151)(H,129,155)(H,130,158)(H,131,153)(H,132,152)(H,144,145)(H,163,164)(H4,102,103,108)(H4,104,105,109)(H4,106,107,110)/t48-,49-,50-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,76-,77-/m0/s1
• InChIKey: MAGGONBKRAPXMU-KJZYAOAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-amino-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-carbamimidamidopentanoic acid
• IUPAC Traditional name: (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-amino-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-carbamimidamidopentanoic acid
• Synonyms: Atrial Natriuretic Peptide Fragment 5-27]; Atriopeptin-23, rat; rANF (103-125); Atriopeptin II rat

Database IDs

• CAS Number: 89139-54-8
• MDL Number: MFCD00076235
• PubChem SID: 162226742
• PubChem CID: 16132367

CALCULATED PROPERTIES

• Acid pKa: 3.2515986
• H Acceptors: 42
• H Donor: 40
• LogD (pH = 5.5): -26.103395
• LogD (pH = 7.4): -24.456553
• Log P: -22.109749
• Molar Refractivity: 615.5104 cm^3
• Polarizability: 227.9974 Å^3
• Polar Surface Area: 1093.62 Å^2
• Rotatable Bonds: 46
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Pharmacology Properties

• Gene Information: rat ... Nppa(24602)

DETAILS

Sigma Aldrich - A9035

Amino Acid Sequence
Ser-Ser-Cys-Phe-Gly-Gly-Arg-Ile-Asp-Arg-Ile-Gly-Ala-Gln-Ser-Gly-Leu-Gly-Cys-Asn-Ser-Phe-Arg
Biochem/physiol Actions
Activates particulate guanylyl cyclase; cardiac atrial peptide which relaxes both intestinal and vascular smooth muscle.