(4S)-4-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-hydroxypropanamido]propanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-4-methylpentanamido]-4-(methylsulfanyl)butanamido]-3-carboxypropanamido]hexanamido]-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}ethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}butanoic acid

• ChemBase ID: 133093
• Molecular Formular: C109H163N25O32S
• Molecular Mass: 2367.67382
• Monoisotopic Mass: 2366.16166918
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](C)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[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)[C@H](CC)C)[C@H](CC)C)CC(=O)O)CC(C)C)Cc1nc[nH]c1)C)Cc1ccccc1)Cc1ccc(cc1)O)C(C)C)C)CCC(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)C)CO)C)CO)CO)CC(C)C)CCSC)CC(=O)O
• InChI: InChI=1S/C109H163N25O32S/c1-16-56(9)87(107(163)128-79(109(165)166)43-64-47-113-68-28-22-21-27-67(64)68)134-108(164)88(57(10)17-2)133-102(158)78(46-85(143)144)126-98(154)73(40-54(5)6)122-100(156)76(44-65-48-112-52-114-65)121-90(146)59(12)116-96(152)74(41-62-25-19-18-20-26-62)124-99(155)75(42-63-30-32-66(138)33-31-63)127-106(162)86(55(7)8)132-92(148)61(14)115-93(149)70(34-35-83(139)140)119-94(150)69(29-23-24-37-110)118-101(157)77(45-84(141)142)125-95(151)71(36-38-167-15)120-97(153)72(39-53(3)4)123-104(160)82(51-137)131-105(161)81(50-136)130-91(147)60(13)117-103(159)80(49-135)129-89(145)58(11)111/h18-22,25-28,30-33,47-48,52-61,69-82,86-88,113,135-138H,16-17,23-24,29,34-46,49-51,110-111H2,1-15H3,(H,112,114)(H,115,149)(H,116,152)(H,117,159)(H,118,157)(H,119,150)(H,120,153)(H,121,146)(H,122,156)(H,123,160)(H,124,155)(H,125,151)(H,126,154)(H,127,162)(H,128,163)(H,129,145)(H,130,147)(H,131,161)(H,132,148)(H,133,158)(H,134,164)(H,139,140)(H,141,142)(H,143,144)(H,165,166)/t56-,57-,58-,59-,60-,61-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,86-,87-,88-/m0/s1
• InChIKey: NRTWVLDGYXCWHD-IGKRDWOESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-hydroxypropanamido]propanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-4-methylpentanamido]-4-(methylsulfanyl)butanamido]-3-carboxypropanamido]hexanamido]-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}ethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-hydroxypropanamido]propanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-4-methylpentanamido]-4-(methylsulfanyl)butanamido]-3-carboxypropanamido]hexanamido]-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}ethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}butanoic acid
• Synonyms: [Ala1,3,11,15]-Endothelin 1

Database IDs

• CAS Number: 121204-87-3
• MDL Number: MFCD00143562
• PubChem SID: 162227370
• PubChem CID: 71308636

CALCULATED PROPERTIES

• Acid pKa: 3.0425818
• H Acceptors: 35
• H Donor: 32
• LogD (pH = 5.5): -13.390192
• LogD (pH = 7.4): -16.120432
• Log P: -11.271682
• Molar Refractivity: 595.7949 cm^3
• Polarizability: 234.999 Å^3
• Polar Surface Area: 908.63 Å^2
• Rotatable Bonds: 75
• 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: human ... EDNRB(1910)mouse ... EDNRB(13618)rat ... EDNRB(50672)

DETAILS

Sigma Aldrich - E6877

Amino Acid Sequence
Ala-Ser-Ala-Ser-Ser-Leu-Met-Asp-Lys-Glu-Ala-Val-Tyr-Phe-Ala-His-Leu-Asp-Ile-Ile-Trp
Biochem/physiol Actions
Selective agonist for ETB endothelin receptors.