(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-hydroxypropanoic acid

• ChemBase ID: 131271
• Molecular Formular: C83H135N29O30S2
• Molecular Mass: 2083.2663
• Monoisotopic Mass: 2081.93710607
• 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)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)O)CO)CC(=O)N)NC(=O)[C@H](CO)N
• InChI: InChI=1S/C83H135N29O30S2/c1-8-39(5)64-79(139)97-29-59(120)98-41(7)66(126)102-46(19-20-56(85)117)71(131)108-51(33-114)70(130)96-30-61(122)100-47(23-38(3)4)68(128)95-31-62(123)101-54(77(137)105-49(25-57(86)118)74(134)109-53(35-116)81(141)142)36-143-144-37-55(110-76(136)52(34-115)107-67(127)43(84)32-113)78(138)104-48(24-42-15-11-10-12-16-42)69(129)94-27-58(119)93-28-60(121)99-44(17-13-21-91-82(87)88)72(132)112-65(40(6)9-2)80(140)106-50(26-63(124)125)75(135)103-45(73(133)111-64)18-14-22-92-83(89)90/h10-12,15-16,38-41,43-55,64-65,113-116H,8-9,13-14,17-37,84H2,1-7H3,(H2,85,117)(H2,86,118)(H,93,119)(H,94,129)(H,95,128)(H,96,130)(H,97,139)(H,98,120)(H,99,121)(H,100,122)(H,101,123)(H,102,126)(H,103,135)(H,104,138)(H,105,137)(H,106,140)(H,107,127)(H,108,131)(H,109,134)(H,110,136)(H,111,133)(H,112,132)(H,124,125)(H,141,142)(H4,87,88,91)(H4,89,90,92)/t39-,40-,41-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,64-,65-/m0/s1
• InChIKey: UXLDAJPPNWDHHB-ZSLGIGMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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-hydroxypropanoic acid
• IUPAC Traditional name: (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-hydroxypropanoic acid
• Synonyms: Atrial Natriuretic Peptide Fragment 5-25; Atriopeptin I rat

Database IDs

• CAS Number: 89139-53-7
• MDL Number: MFCD00076234
• PubChem SID: 162225549
• PubChem CID: 16132366

CALCULATED PROPERTIES

• Acid pKa: 2.9879415
• H Acceptors: 37
• H Donor: 35
• LogD (pH = 5.5): -23.359434
• LogD (pH = 7.4): -21.723545
• Log P: -21.356274
• Molar Refractivity: 522.8708 cm^3
• Polarizability: 196.44371 Å^3
• Polar Surface Area: 973.52 Å^2
• Rotatable Bonds: 36
• 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)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - A9160

Biochem/physiol Actions
Weak agonist at the cGMP-coupled ANF receptor; cardiac atrial peptide which selectively relaxes intestinal but not vascular smooth muscle.