(3S)-3-[(2S)-2-[(2S)-2-{[(1R,4S,7S,10S,13S,16S,19S,22S,25R,28S,31R,36R,39S,42S,45S)-31-amino-22-(4-aminobutyl)-39-benzyl-42-(carbamoylmethyl)-4,7-bis(2-carboxyethyl)-10,19-bis(carboxymethyl)-13,28-bis[(1R)-1-hydroxyethyl]-45-(2-methylpropyl)-16-[2-(methylsulfanyl)ethyl]-3,6,9,12,15,18,21,24,27,30,38,41,44,47-tetradecaoxo-33,34,49,50-tetrathia-2,5,8,11,14,17,20,23,26,29,37,40,43,46-tetradecaazabicyclo[23.22.4]henpentacontan-36-yl]formamido}-3-(1H-imidazol-4-yl)propanamido]-4-carbamoylbutanamido]-3-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylpropyl]carbamoyl}propanoic acid

• ChemBase ID: 153214
• Molecular Formular: C105H153N27O36S5
• Molecular Mass: 2529.82262
• Monoisotopic Mass: 2527.95750935
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)Cc1ccccc1)CC(=O)N)CC(C)C)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](NC2=O)CCCCN)CC(=O)O)CCSC)[C@@H](C)O)CC(=O)O)CCC(=O)O)CCC(=O)O)[C@@H](C)O)N
• Canonical SMILES: NCCCC[C@@H]1NC(=O)[C@@H]2CSSC[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC(=O)O)CCSC)[C@H](O)C)CC(=O)O)CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N2)[C@H](O)C)N)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(C)C)CC(=O)O)CCC(=O)N)Cc1nc[nH]c1)Cc1ccccc1
• InChI: InChI=1S/C105H153N27O36S5/c1-10-49(6)82(102(164)125-70(105(167)168)34-53-40-111-57-21-15-14-20-55(53)57)130-101(163)81(48(4)5)129-97(159)69(39-80(145)146)123-88(150)59(23-26-74(108)135)115-93(155)65(35-54-41-110-46-112-54)120-100(162)72-43-171-170-42-56(107)85(147)131-83(50(7)133)104(166)128-73-45-173-172-44-71(99(161)118-63(32-47(2)3)91(153)121-66(36-75(109)136)94(156)119-64(92(154)127-72)33-52-18-12-11-13-19-52)126-89(151)61(25-28-77(139)140)114-87(149)60(24-27-76(137)138)116-96(158)68(38-79(143)144)124-103(165)84(51(8)134)132-90(152)62(29-31-169-9)117-95(157)67(37-78(141)142)122-86(148)58(113-98(73)160)22-16-17-30-106/h11-15,18-21,40-41,46-51,56,58-73,81-84,111,133-134H,10,16-17,22-39,42-45,106-107H2,1-9H3,(H2,108,135)(H2,109,136)(H,110,112)(H,113,160)(H,114,149)(H,115,155)(H,116,158)(H,117,157)(H,118,161)(H,119,156)(H,120,162)(H,121,153)(H,122,148)(H,123,150)(H,124,165)(H,125,164)(H,126,151)(H,127,154)(H,128,166)(H,129,159)(H,130,163)(H,131,147)(H,132,152)(H,137,138)(H,139,140)(H,141,142)(H,143,144)(H,145,146)(H,167,168)/t49-,50+,51+,56-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,81-,82-,83-,84-/m0/s1
• InChIKey: VNBOQGHLRDYRCV-LFHFUXDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-{[(1R,4S,7S,10S,13S,16S,19S,22S,25R,28S,31R,36R,39S,42S,45S)-31-amino-22-(4-aminobutyl)-39-benzyl-42-(carbamoylmethyl)-4,7-bis(2-carboxyethyl)-10,19-bis(carboxymethyl)-13,28-bis[(1R)-1-hydroxyethyl]-45-(2-methylpropyl)-16-[2-(methylsulfanyl)ethyl]-3,6,9,12,15,18,21,24,27,30,38,41,44,47-tetradecaoxo-33,34,49,50-tetrathia-2,5,8,11,14,17,20,23,26,29,37,40,43,46-tetradecaazabicyclo[23.22.4]henpentacontan-36-yl]formamido}-3-(1H-imidazol-4-yl)propanamido]-4-carbamoylbutanamido]-3-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylpropyl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-{[(1R,4S,7S,10S,13S,16S,19S,22S,25R,28S,31R,36R,39S,42S,45S)-31-amino-22-(4-aminobutyl)-39-benzyl-42-(carbamoylmethyl)-4,7-bis(2-carboxyethyl)-10,19-bis(carboxymethyl)-13,28-bis[(1R)-1-hydroxyethyl]-45-(2-methylpropyl)-16-[2-(methylsulfanyl)ethyl]-3,6,9,12,15,18,21,24,27,30,38,41,44,47-tetradecaoxo-33,34,49,50-tetrathia-2,5,8,11,14,17,20,23,26,29,37,40,43,46-tetradecaazabicyclo[23.22.4]henpentacontan-36-yl]formamido}-3-(1H-imidazol-4-yl)propanamido]-4-carbamoylbutanamido]-3-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylpropyl]carbamoyl}propanoic acid
• Synonyms: Sarafotoxin 6c, [Lys4]-; Sarafotoxin 6c, [Lys4]-

Database IDs

• MDL Number: MFCD00133969
• PubChem SID: 162247353
• PubChem CID: 71311615

CALCULATED PROPERTIES

• Acid pKa: 2.7462642
• H Acceptors: 39
• H Donor: 34
• LogD (pH = 5.5): -22.425846
• LogD (pH = 7.4): -29.067139
• Log P: -16.250546
• Molar Refractivity: 614.2691 cm^3
• Polarizability: 242.62311 Å^3
• Polar Surface Area: 1028.95 Å^2
• Rotatable Bonds: 50
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Mol. Weight: mol wt 2530 (peptide free base)
• Linear Formula: C105H153O36N27S5

DETAILS

Sigma Aldrich - S157

Application
Selective ETB endothelin receptor agonist.
Other Notes
Peptide content and salt form information are provided with each lot.