(2S)-2-[(2S)-2-[(2S)-2-(2-{[(4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,43S,49S,52R)-52-amino-49-benzyl-28,37-bis[(2S)-butan-2-yl]-31,40-bis(3-carbamimidamidopropyl)-19-(2-carbamoylethyl)-34-(carboxymethyl)-16,43-bis(hydroxymethyl)-22-methyl-10-[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-hexadecaazacyclotripentacontan-4-yl]formamido}acetamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-phenylpropanoic acid

• ChemBase ID: 134279
• Molecular Formular: C93H150N34O27S3
• Molecular Mass: 2272.5927
• Monoisotopic Mass: 2271.05717871
• 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)[C@@H](C)CC)CCCNC(=N)N)CO)Cc1ccccc1)N)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)CCSC)CO)CCC(=O)N)C
• Canonical SMILES: CSCC[C@@H]1NC(=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](CCCNC(=N)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CSSC[C@H](NC(=O)CNC1=O)C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccccc1)CCCNC(=N)N)CCCNC(=N)N)N)Cc1ccccc1)CO)CCCNC(=N)N)[C@H](CC)C)[C@H](CC)C
• InChI: InChI=1S/C93H150N34O27S3/c1-7-47(3)72-87(151)112-38-66(131)113-49(5)74(138)118-57(27-28-65(95)130)82(146)125-62(43-128)78(142)110-39-68(133)115-58(29-34-155-6)76(140)108-42-70(135)117-64(79(143)111-40-67(132)114-53(23-15-30-104-90(96)97)80(144)119-54(24-16-31-105-91(98)99)81(145)124-61(89(153)154)36-51-21-13-10-14-22-51)46-157-156-45-52(94)75(139)122-59(35-50-19-11-9-12-20-50)77(141)109-41-69(134)116-63(44-129)86(150)121-56(26-18-33-107-93(102)103)84(148)127-73(48(4)8-2)88(152)123-60(37-71(136)137)85(149)120-55(83(147)126-72)25-17-32-106-92(100)101/h9-14,19-22,47-49,52-64,72-73,128-129H,7-8,15-18,23-46,94H2,1-6H3,(H2,95,130)(H,108,140)(H,109,141)(H,110,142)(H,111,143)(H,112,151)(H,113,131)(H,114,132)(H,115,133)(H,116,134)(H,117,135)(H,118,138)(H,119,144)(H,120,149)(H,121,150)(H,122,139)(H,123,152)(H,124,145)(H,125,146)(H,126,147)(H,127,148)(H,136,137)(H,153,154)(H4,96,97,104)(H4,98,99,105)(H4,100,101,106)(H4,102,103,107)/t47-,48-,49-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,72-,73-/m0/s1
• InChIKey: ICYRDBKHDKQDON-SMFLCKQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-(2-{[(4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,43S,49S,52R)-52-amino-49-benzyl-28,37-bis[(2S)-butan-2-yl]-31,40-bis(3-carbamimidamidopropyl)-19-(2-carbamoylethyl)-34-(carboxymethyl)-16,43-bis(hydroxymethyl)-22-methyl-10-[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-hexadecaazacyclotripentacontan-4-yl]formamido}acetamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-(2-{[(4R,10S,16S,19S,22S,28S,31S,34S,37S,40S,43S,49S,52R)-52-amino-49-benzyl-28,37-bis[(2S)-butan-2-yl]-31,40-bis(3-carbamimidamidopropyl)-19-(2-carbamoylethyl)-34-(carboxymethyl)-16,43-bis(hydroxymethyl)-22-methyl-10-[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-hexadecaazacyclotripentacontan-4-yl]formamido}acetamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-phenylpropanoic acid
• Synonyms: ANF 4-24; fANP-21; Atrial Natriuretic Peptide fragment 4-24 frog

Database IDs

• CAS Number: 118691-44-4
• MDL Number: MFCD00076224
• PubChem SID: 162228556
• PubChem CID: 16173282

CALCULATED PROPERTIES

• Acid pKa: -1.0204927
• H Acceptors: 40
• H Donor: 38
• LogD (pH = 5.5): -25.51554
• LogD (pH = 7.4): -23.83295
• Log P: -18.998522
• Molar Refractivity: 606.8115 cm^3
• Polarizability: 219.74936 Å^3
• Polar Surface Area: 1013.77 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: African clawed frog ... anf-A(394320)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - A0804

Amino Acid Sequence
Cys-Phe-Gly-Ser-Arg-Ile-Asp-Arg-Ile-Gly-Ala-Gln-Ser-Gly-Met-Gly-Cys-Gly-Arg-Arg-Phe [Disulfide bridge: 4—20]
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.