(4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pentyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-phenylethyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylbutanamido]propanamido]-3-hydroxypropanamido]butanoic acid

• ChemBase ID: 153618
• Molecular Formular: C112H178N36O27
• Molecular Mass: 2460.83672
• Monoisotopic Mass: 2459.36621462
• SMILES: C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)N
• Canonical SMILES: NCCCC[C@@H](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)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCNC(=N)N)CO)CC(C)C)C)Cc1c[nH]c2c1cccc2)CCCCN)CC(=O)N)Cc1c[nH]c2c1cccc2)CCCCN)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)C)CCCNC(=N)N)CC(C)C)CC(=O)O)C)CO)CCC(=O)O)Cc1ccccc1)CCCNC(=N)N
• InChI: InChI=1S/C112H178N36O27/c1-57(2)46-77(102(168)147-85(56-150)107(173)132-70(90(118)156)35-23-43-125-110(119)120)139-92(158)61(8)130-100(166)80(49-64-53-128-68-30-15-13-28-66(64)68)142-97(163)73(34-19-22-42-115)136-105(171)82(51-86(117)151)144-104(170)81(50-65-54-129-69-31-16-14-29-67(65)69)143-96(162)72(33-18-21-41-114)135-94(160)71(32-17-20-40-113)134-95(161)75(37-25-45-127-112(123)124)137-103(169)79(48-63-26-11-10-12-27-63)141-99(165)76(38-39-87(152)153)138-108(174)84(55-149)146-93(159)62(9)131-109(175)89(59(5)6)148-106(172)83(52-88(154)155)145-101(167)78(47-58(3)4)140-98(164)74(133-91(157)60(7)116)36-24-44-126-111(121)122/h10-16,26-31,53-54,57-62,70-85,89,128-129,149-150H,17-25,32-52,55-56,113-116H2,1-9H3,(H2,117,151)(H2,118,156)(H,130,166)(H,131,175)(H,132,173)(H,133,157)(H,134,161)(H,135,160)(H,136,171)(H,137,169)(H,138,174)(H,139,158)(H,140,164)(H,141,165)(H,142,163)(H,143,162)(H,144,170)(H,145,167)(H,146,159)(H,147,168)(H,148,172)(H,152,153)(H,154,155)(H4,119,120,125)(H4,121,122,126)(H4,123,124,127)/t60-,61-,62-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,89-/m0/s1
• InChIKey: PIRWNASAJNPKHT-SHZATDIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pentyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-phenylethyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylbutanamido]propanamido]-3-hydroxypropanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pentyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-phenylethyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylbutanamido]propanamido]-3-hydroxypropanamido]butanoic acid
• Synonyms: PAMP; Proadrenomedullin Fragment 1-20 human

Database IDs

• CAS Number: 150238-87-2
• MDL Number: MFCD01076554
• PubChem SID: 162247757
• PubChem CID: 71311703

CALCULATED PROPERTIES

• Acid pKa: 3.3211799
• H Acceptors: 40
• H Donor: 40
• LogD (pH = 5.5): -25.469015
• LogD (pH = 7.4): -24.189938
• Log P: -14.425985
• Molar Refractivity: 663.3277 cm^3
• Polarizability: 248.9475 Å^3
• Polar Surface Area: 1075.5 Å^2
• Rotatable Bonds: 83
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

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

Pharmacology Properties

• Gene Information: human ... ADM(133)

Product Information

• Purity: >93% (HPLC)
• Empirical Formula (Hill Notation): C112H178N36O27

DETAILS

Sigma Aldrich - P4613

Amino Acid Sequence
Ala-Arg-Leu-Asp-Val-Ala-Ser-Glu-Phe-Arg-Lys-Lys-Trp-Asn-Lys-Trp-Ala-Leu-Ser-Arg-NH2
Biochem/physiol Actions
Precursor of adrenomedullin producing rapid and hypotensive effects and suggested to function as an inhibitory modulator of renal noradrenergic neurotransmission, regulates renal function, inhibitory regulator of adrenal catecholamine release and induces potent hyperglycemic effects.