methyl (1S,2R,18R,19R,22R,34S,37R)-22-amino-2-{[(2R,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-64-{[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-18,26,31,44,49-pentahydroxy-30-methyl-21,35,38,54,56,59-hexaoxo-47-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7,13,28-trioxa-20,36,39,53,55,58-hexaazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8(64),9,11,14,16,23,25,27(61),29(60),30,32,41,43,45(57),46,48,50,62,65-henicosaene-52-carboxylate

• ChemBase ID: 155557
• Molecular Formular: C95H110N8O44
• Molecular Mass: 2067.9171
• Monoisotopic Mass: 2066.66158884
• SMILES: Cc1c(cc2cc1Oc1cc(ccc1O)[C@H](C(=O)N[C@@H]1[C@@H](c3ccc(cc3)Oc3cc4cc(c3O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)O)O)O[C@@H]3[C@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O[C@H]3[C@H]([C@@H]([C@@H](CO3)O)O)O)Oc3ccc(cc3)[C@H]([C@H]3C(=O)NC(c5cc(cc(c5c5cc(ccc5O)C(C(=O)N3)NC(=O)[C@@H]4NC(=O)[C@H]2NC1=O)O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C(=O)OC)O[C@H]1C[C@H]([C@H]([C@@H](O1)C)O)N)O)N)O
• Canonical SMILES: OC[C@H]1O[C@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)Oc2c3Oc4ccc(cc4)[C@@H](O[C@H]4C[C@@H](N)[C@H]([C@@H](O4)C)O)[C@@H]4NC(=O)C(NC(=O)[C@H]5c(c3)cc2Oc2ccc(cc2)[C@@H](O)[C@@H]2C(=O)N[C@H](C(=O)N5)c3cc(O)c(c(c3)Oc3cc([C@H](C(=O)N2)N)ccc3O)C)c2ccc(c(c2)c2c(C(NC4=O)C(=O)OC)cc(cc2O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@@H]2O)O)O)O)O)[C@H]([C@H]([C@@H]1O)O)O[C@@H]1OC[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C95H110N8O44/c1-30-47(109)18-37-20-49(30)139-50-19-35(9-16-46(50)108)59(97)84(125)102-64-68(113)33-5-11-40(12-6-33)137-52-21-38-22-53(81(52)145-95-83(76(121)72(117)56(143-95)29-134-91-78(123)73(118)67(112)32(3)136-91)147-94-82(75(120)71(116)55(27-105)142-94)146-92-77(122)69(114)48(110)28-133-92)138-41-13-7-34(8-14-41)80(144-57-25-44(96)66(111)31(2)135-57)65-89(130)101-63(90(131)132-4)43-23-39(106)24-51(140-93-79(124)74(119)70(115)54(26-104)141-93)58(43)42-17-36(10-15-45(42)107)60(85(126)103-65)98-87(128)62(38)99-86(127)61(37)100-88(64)129/h5-24,31-32,44,48,54-57,59-80,82-83,91-95,104-124H,25-29,96-97H2,1-4H3,(H,98,128)(H,99,127)(H,100,129)(H,101,130)(H,102,125)(H,103,126)/t31-,32-,44+,48+,54+,55+,56+,57-,59+,60?,61-,62+,63?,64+,65-,66-,67-,68+,69+,70+,71+,72+,73+,74-,75-,76-,77-,78+,79-,80+,82-,83+,91+,92-,93+,94+,95-/m0/s1
• InChIKey: VUOPFFVAZTUEGW-ZNAZZOOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,2R,18R,19R,22R,34S,37R)-22-amino-2-{[(2R,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-64-{[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-18,26,31,44,49-pentahydroxy-30-methyl-21,35,38,54,56,59-hexaoxo-47-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7,13,28-trioxa-20,36,39,53,55,58-hexaazaundecacyclo[38.14.2.2^3,^6.2^1^4,^1^7.2^1^9,^3^4.1^8,^1^2.1^2^3,^2^7.1^2^9,^3^3.1^4^1,^4^5.0^1^0,^3^7.0^4^6,^5^1]hexahexaconta-3,5,8(64),9,11,14,16,23,25,27(61),29(60),30,32,41,43,45(57),46,48,50,62,65-henicosaene-52-carboxylate
• IUPAC Traditional name: methyl (1S,2R,18R,19R,22R,34S,37R)-22-amino-2-{[(2R,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-64-{[(2S,3R,4S,5S,6R)-3-{[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-18,26,31,44,49-pentahydroxy-30-methyl-21,35,38,54,56,59-hexaoxo-47-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7,13,28-trioxa-20,36,39,53,55,58-hexaazaundecacyclo[38.14.2.2^3,^6.2^1^4,^1^7.2^1^9,^3^4.1^8,^1^2.1^2^3,^2^7.1^2^9,^3^3.1^4^1,^4^5.0^1^0,^3^7.0^4^6,^5^1]hexahexaconta-3,5,8(64),9,11,14,16,23,25,27(61),29(60),30,32,41,43,45(57),46,48,50,62,65-henicosaene-52-carboxylate
• Synonyms: Ristocetin sulfate salt; Ristomycin monosulfate

Database IDs

• CAS Number: 11140-99-1
• MDL Number: MFCD00076121
• PubChem SID: 24899399; 162249695
• PubChem CID: 16219933

CALCULATED PROPERTIES

• Acid pKa: 7.2754326
• H Acceptors: 42
• H Donor: 29
• LogD (pH = 5.5): -11.215931
• LogD (pH = 7.4): -8.410837
• Log P: -7.821809
• Molar Refractivity: 481.6159 cm^3
• Polarizability: 195.0123 Å^3
• Polar Surface Area: 816.22 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: VJ8650000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% ristocetin A basis (balance primarily Ristocetin B)
• Empirical Formula (Hill Notation): C95H110N8O44 · H2SO4

DETAILS

Sigma Aldrich - R7752

Biochem/physiol Actions
Ristocetin activates platelets. Ristocetin-induced platelet agglutination (RIPA) is decreased in patients undergoing chronic hemodialysis. Together with increased plasma glycocalicin levels (a product of enzymatic cleavage of GPIb), RIPA may contribute to diminished platelet adhesion to vascular subendothelium and increased bleeding associated with uremia. Addition of ristocetin and vWf caused specific agglutination of rGPIbα-liposomes suporting the potential use of rGPIbα-liposomes to enhance platelet function in vivo and support hemostasis in thrombocytopenic individuals.
Other Notes
Glycopeptide antibiotic complex