(3S)-3-[(2S)-2-[(2S)-2-{[(1R,4S,7S,10S,13S,16S,19S,22S,25R,28S,31R,36R,39S,42S,45S)-31-amino-7,22-bis(4-aminobutyl)-39-benzyl-42-(carbamoylmethyl)-4-(2-carboxyethyl)-10,19-bis(carboxymethyl)-13-[(1R)-1-hydroxyethyl]-28-(hydroxymethyl)-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: 133411
• Molecular Formular: C105H156N28O34S5
• Molecular Mass: 2514.85434
• Monoisotopic Mass: 2512.99422921
• 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)CCCCN)CCC(=O)O)CO)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)CCCCN)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)CO)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/C105H156N28O34S5/c1-9-51(6)83(103(164)126-71(105(166)167)35-54-41-112-58-22-14-13-21-56(54)58)132-102(163)82(50(4)5)131-97(158)70(40-81(144)145)124-88(149)61(25-27-76(109)136)117-93(154)66(36-55-42-111-48-113-55)121-101(162)75-45-170-169-44-57(108)85(146)127-72(43-134)98(159)130-73-46-171-172-47-74(100(161)119-64(33-49(2)3)91(152)122-67(37-77(110)137)94(155)120-65(92(153)129-75)34-53-19-11-10-12-20-53)128-89(150)62(26-28-78(138)139)116-86(147)59(23-15-17-30-106)114-96(157)69(39-80(142)143)125-104(165)84(52(7)135)133-90(151)63(29-32-168-8)118-95(156)68(38-79(140)141)123-87(148)60(115-99(73)160)24-16-18-31-107/h10-14,19-22,41-42,48-52,57,59-75,82-84,112,134-135H,9,15-18,23-40,43-47,106-108H2,1-8H3,(H2,109,136)(H2,110,137)(H,111,113)(H,114,157)(H,115,160)(H,116,147)(H,117,154)(H,118,156)(H,119,161)(H,120,155)(H,121,162)(H,122,152)(H,123,148)(H,124,149)(H,125,165)(H,126,164)(H,127,146)(H,128,150)(H,129,153)(H,130,159)(H,131,158)(H,132,163)(H,133,151)(H,138,139)(H,140,141)(H,142,143)(H,144,145)(H,166,167)/t51-,52+,57-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,82-,83-,84-/m0/s1
• InChIKey: BOQKWORWRAYXSI-SQCNKGOOSA-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-7,22-bis(4-aminobutyl)-39-benzyl-42-(carbamoylmethyl)-4-(2-carboxyethyl)-10,19-bis(carboxymethyl)-13-[(1R)-1-hydroxyethyl]-28-(hydroxymethyl)-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-7,22-bis(4-aminobutyl)-39-benzyl-42-(carbamoylmethyl)-4-(2-carboxyethyl)-10,19-bis(carboxymethyl)-13-[(1R)-1-hydroxyethyl]-28-(hydroxymethyl)-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 S6a1

Database IDs

• CAS Number: 119965-38-7
• MDL Number: MFCD00133808
• PubChem SID: 162227688
• PubChem CID: 71308664

CALCULATED PROPERTIES

• Acid pKa: 2.8557975
• H Acceptors: 38
• H Donor: 34
• LogD (pH = 5.5): -21.151682
• LogD (pH = 7.4): -24.724035
• Log P: -18.773535
• Molar Refractivity: 616.3721 cm^3
• Polarizability: 243.50412 Å^3
• Polar Surface Area: 1017.67 Å^2
• Rotatable Bonds: 51
• 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

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - S1522

Amino Acid Sequence
Cys-Ser-Cys-Lys-Asp-Met-Thr-Asp-Lys-Glu-Cys-Leu-Asn-Phe-Cys-His-Gln-Asp-Val-Ile-Trp [Disulfide Bridges: 1-15, 3-11]