(4S)-4-amino-4-{[(1R,7S,10S,13S,16S,19R,24R,27S,33S,36S,43R)-7-(3-carbamimidamidopropyl)-19-carbamoyl-27-(carbamoylmethyl)-16-(hydroxymethyl)-13-[(4-hydroxyphenyl)methyl]-10-(1H-imidazol-4-ylmethyl)-36-methyl-2,5,8,11,14,17,25,28,34,37,44-undecaoxo-21,22,40,41-tetrathia-3,6,9,12,15,18,26,29,35,38,45-undecaazatricyclo[22.14.7.029,33]pentatetracontan-43-yl]carbamoyl}butanoic acid

• ChemBase ID: 153518
• Molecular Formular: C55H80N20O18S4
• Molecular Mass: 1437.6069
• Monoisotopic Mass: 1436.48422982
• SMILES: C[C@H]1C(=O)N[C@H]2CSSC[C@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)CNC2=O)CCCNC(=N)N)Cc2c[nH]cn2)Cc2ccc(cc2)O)CO)C(=O)N)C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N1)CC(=O)N)NC(=O)[C@@H](CCC(=O)O)N
• Canonical SMILES: OC[C@@H]1NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@@H](Cc2c[nH]cn2)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)[C@@H]2CSSC[C@H](C(=O)N[C@@H](CSSC[C@H](NC1=O)C(=O)N)C(=O)N[C@@H](CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N2)C)NC(=O)[C@@H](CCC(=O)O)N
• InChI: InChI=1S/C55H80N20O18S4/c1-25-44(83)72-36-21-95-97-22-37(73-45(84)29(56)10-11-42(80)81)52(91)74-38(51(90)69-33(16-40(57)78)54(93)75-13-3-5-39(75)53(92)65-25)23-96-94-20-35(43(58)82)71-50(89)34(19-76)70-48(87)31(14-26-6-8-28(77)9-7-26)67-49(88)32(15-27-17-61-24-64-27)68-47(86)30(4-2-12-62-55(59)60)66-41(79)18-63-46(36)85/h6-9,17,24-25,29-39,76-77H,2-5,10-16,18-23,56H2,1H3,(H2,57,78)(H2,58,82)(H,61,64)(H,63,85)(H,65,92)(H,66,79)(H,67,88)(H,68,86)(H,69,90)(H,70,87)(H,71,89)(H,72,83)(H,73,84)(H,74,91)(H,80,81)(H4,59,60,62)/t25-,29-,30-,31-,32?,33-,34-,35?,36-,37-,38-,39-/m0/s1
• InChIKey: HWYLVHOPQMLNRJ-LQXBVDJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-amino-4-{[(1R,7S,10S,13S,16S,19R,24R,27S,33S,36S,43R)-7-(3-carbamimidamidopropyl)-19-carbamoyl-27-(carbamoylmethyl)-16-(hydroxymethyl)-13-[(4-hydroxyphenyl)methyl]-10-(1H-imidazol-4-ylmethyl)-36-methyl-2,5,8,11,14,17,25,28,34,37,44-undecaoxo-21,22,40,41-tetrathia-3,6,9,12,15,18,26,29,35,38,45-undecaazatricyclo[22.14.7.0^2^9,^3^3]pentatetracontan-43-yl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-amino-4-{[(1R,7S,10S,13S,16S,19R,24R,27S,33S,36S,43R)-7-(3-carbamimidamidopropyl)-19-carbamoyl-27-(carbamoylmethyl)-16-(hydroxymethyl)-13-[(4-hydroxyphenyl)methyl]-10-(1H-imidazol-4-ylmethyl)-36-methyl-2,5,8,11,14,17,25,28,34,37,44-undecaoxo-21,22,40,41-tetrathia-3,6,9,12,15,18,26,29,35,38,45-undecaazatricyclo[22.14.7.0^2^9,^3^3]pentatetracontan-43-yl]carbamoyl}butanoic acid
• Synonyms: Conotoxin GI

Database IDs

• CAS Number: 76862-65-2
• MDL Number: MFCD00167555
• PubChem SID: 24893090; 162247657
• PubChem CID: 25084230

CALCULATED PROPERTIES

• Molar Refractivity: 358.0513 cm^3
• Polarizability: 135.549 Å^3
• Polar Surface Area: 620.95 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false
• Acid pKa: 3.5674753
• H Acceptors: 23
• H Donor: 21
• LogD (pH = 5.5): -16.316576
• LogD (pH = 7.4): -13.905079
• Log P: -13.212401

PROPERTIES

Safety Information

• RTECS: GL1500000
• 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 ... TAC1(6863), TACR1(6869)mouse ... TAC1(21333), TACR1(21336)rat ... TAC1(24806), TACR1(24807)

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C55H80N20O18S4

DETAILS

Sigma Aldrich - C8653

Amino Acid Sequence
Glu-Cys-Cys-Asn-Pro-Ala-Cys-Gly-Arg-His-Tyr-Ser-Cys-NH2, [Disulfide Bridges: 2-7, 3-13]
Biochem/physiol Actions
Postsynaptic inhibitor at the neuromuscular junction