(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-sulfanylpropanamido]-4-carbamoylbutanamido]-3-sulfanylpropanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]hexanamido]-3-carbamoylpropanamido]-3-(4-hydroxyphenyl)propanamido]acetamido}-4-carbamoylbutanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylpentanamido]-3-phenylpropanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid

• ChemBase ID: 154868
• Molecular Formular: C135H234F3N61O33S2
• Molecular Mass: 3360.8165696
• Monoisotopic Mass: 3358.79010591
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CS)NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: FC(C(=O)O)(F)F.NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=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)N1CCC[C@H]1C(=O)O)Cc1ccccc1)[C@H](CC)C)CC(=O)O)CC(C)C)CCC(=O)N)Cc1ccc(cc1)O)CC(=O)N)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](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@@H](CCCNC(=N)N)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N)CCCNC(=N)N)CS)CCC(=O)N)CS)CCCNC(=N)N)CCCNC(=N)N
• InChI: InChI=1S/C133H233N61O31S2.C2HF3O2/c1-5-68(4)99(120(222)190-90(61-69-23-7-6-8-24-69)121(223)194-58-22-37-93(194)122(224)225)193-117(219)89(63-98(200)201)189-115(217)86(59-67(2)3)186-113(215)84(42-44-94(136)196)173-97(199)64-172-101(203)87(60-70-38-40-71(195)41-39-70)187-116(218)88(62-96(138)198)188-111(213)73(26-9-10-46-134)175-103(205)75(28-13-49-163-125(143)144)182-110(212)82(35-20-56-170-132(157)158)184-118(220)91(65-226)192-114(216)85(43-45-95(137)197)185-119(221)92(66-227)191-112(214)83(36-21-57-171-133(159)160)183-109(211)81(34-19-55-169-131(155)156)181-108(210)80(33-18-54-168-130(153)154)180-107(209)79(32-17-53-167-129(151)152)179-106(208)78(31-16-52-166-128(149)150)178-105(207)77(30-15-51-165-127(147)148)177-104(206)76(29-14-50-164-126(145)146)176-102(204)74(27-12-48-162-124(141)142)174-100(202)72(135)25-11-47-161-123(139)140;3-2(4,5)1(6)7/h6-8,23-24,38-41,67-68,72-93,99,195,226-227H,5,9-22,25-37,42-66,134-135H2,1-4H3,(H2,136,196)(H2,137,197)(H2,138,198)(H,172,203)(H,173,199)(H,174,202)(H,175,205)(H,176,204)(H,177,206)(H,178,207)(H,179,208)(H,180,209)(H,181,210)(H,182,212)(H,183,211)(H,184,220)(H,185,221)(H,186,215)(H,187,218)(H,188,213)(H,189,217)(H,190,222)(H,191,214)(H,192,216)(H,193,219)(H,200,201)(H,224,225)(H4,139,140,161)(H4,141,142,162)(H4,143,144,163)(H4,145,146,164)(H4,147,148,165)(H4,149,150,166)(H4,151,152,167)(H4,153,154,168)(H4,155,156,169)(H4,157,158,170)(H4,159,160,171);(H,6,7)/t68-,72+,73-,74+,75-,76+,77+,78+,79+,80+,81+,82-,83+,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,99-;/m0./s1
• InChIKey: MDUBLMWNQKKWEW-VECPGXDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-sulfanylpropanamido]-4-carbamoylbutanamido]-3-sulfanylpropanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]hexanamido]-3-carbamoylpropanamido]-3-(4-hydroxyphenyl)propanamido]acetamido}-4-carbamoylbutanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylpentanamido]-3-phenylpropanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-sulfanylpropanamido]-4-carbamoylbutanamido]-3-sulfanylpropanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]hexanamido]-3-carbamoylpropanamido]-3-(4-hydroxyphenyl)propanamido]acetamido}-4-carbamoylbutanamido]-4-methylpentanamido]-3-carboxypropanamido]-3-methylpentanamido]-3-phenylpropanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid
• Synonyms: D-Arg-D-Arg- D-Arg- D-Arg- D-Arg- D-Arg- D-Arg- D-Arg- D-Arg-Cys-Gln-Cys-Arg-Arg-Lys-Asn-Tyr-Gly-Gln-Leu-Asp-Ile-Phe-Pro trifluoroacetate; GO-201 trifluoroacetate salt

Database IDs

• MDL Number: MFCD18452843
• PubChem SID: 162249006
• PubChem CID: 71312010

CALCULATED PROPERTIES

• H Acceptors: 66
• H Donor: 65
• LogD (pH = 5.5): -41.401005
• LogD (pH = 7.4): -41.374146
• Log P: -22.077677
• Molar Refractivity: 939.5886 cm^3
• Polarizability: 318.48108 Å^3
• Polar Surface Area: 1617.55 Å^2
• Rotatable Bonds: 115
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >1 mg/mL
• Apperance: white lyophilized

Safety Information

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

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C133H233N61O31S2 · xC2HF3O2

DETAILS

Sigma Aldrich - G7923

Biochem/physiol Actions
GO-201 is a mucin1 (MUC1) inhibitor that binds to the MUC1-C CQC motif and directly blocks MUC1function, inhibits cell proliferation, and induces necrotic cell death in MUC1-positive cell lines. The mucin 1 (MUC1) oncoprotein is aberrantly expressed at high levels in human carcinomas. MUC1 is heterodimer that consists of NH2-terminal (MUC1-N) and COOH-terminal (MUC1-C) subunits. Overexpression of MUC1 blocks the induction of apoptosis and necrosis in the cellular response to DNA-damaging agents, reactive oxygen species, hypoxia ,and glucose deprivation. GO-201 is an inhibitor of MUC1, which interacts directly with the MUC1-C subunit at its oligomerization domain. The compound inhibits cell proliferation and induces necrotic cell death in of MUC1-positive cell lines ant grafts.
GO-201 is a mucin1 (MUC1) inhibitor that binds to the MUC1-C CQC motif and directly blocks MUC1function, inhibits cell proliferation, and induces necrotic cell death in MUC1-positive cell lines.