Pneumocandin B0 CAS#: 135575-42-7
IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Product NamePneumocandin B0IUPAC NameN--6--11,20,21,25-tetrahydroxy-15--2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricycloheptacosan-18-yl]-10,12-dimethyltetradecanamide Molecular Structure
CAS Registry Number 135575-42-7EINECS NumberNo data availableMDL NumberNo data availableBeilstein Registry NumberNo data availableSynonymspneumocandin B0,
pneumocandin Bo,
pneumocandin B,
pneumocandin B0,
L-688,
786
CAS 135575-42-7
CAS: 135575-42-7
CAS No.: 135575-42-7 Molecular FormulaC50H80N8O17 Molecular Weight1065.2136 SMILES CCC(C)CC(C)CCCCCCCCC(=O)N1C((NC(=O)2(CCN2C(=O)(NC(=O)(NC(=O)3C(CN3C(=O)(NC1=O)(C)O)O)((c4ccc(cc4)O)O)O)(CC(=O)N)O)O)O)O InChIInChI=1S/C50H80N8O17/c1-5-25(2)20-26(3)12-10-8-6-7-9-11-13-37(66)52-31-22-35(64)46(71)56-48(73)41-33(62)18-19-57(41)50(75)39(34(63)23-36(51)65)54-47(72)40(43(68)42(67)28-14-16-29(60)17-15-28)55-45(70)32-21-30(61)24-58(32)49(74)38(27(4)59)53-44(31)69/h14-17,25-27,30-35,38-43,46,59-64,67-68,71H,5-13,18-24H2,1-4H3,(H2,51,65)(H,52,66)(H,53,69)(H,54,72)(H,55,70)(H,56,73)/t25?,26?,27-,30-,31+,32+,33+,34-,35-,38+,39+,40+,41+,42+,43+,46-/m1/s1 InChI KeyDQXPFAADCTZLNL-ZESADUFFSA-N Canonical SMILESCCC(C)CC(C)CCCCCCCCC(=O)NC1CC(C(NC(=O)C2C(CCN2C(=O)C(NC(=O)C(NC(=O)C3CC(CN3C(=O)C(NC1=O)C(C)O)O)C(C(C4=CC=C(C=C4)O)O)O)C(CC(=O)N)O)O)O)O
Patent InformationPatent IDTitlePublication DateUS2014/58082 INTERMEDIATE FOR SYNTHESIZING CASPOFUNGIN AND PREPARATION METHOD THEREOF 2014
AppearanceOff white powder SolubilityNo data availableBoiling point1442.9±65.0 °C(Predicted) Flash PointNo data available Refractive indexNo data available SensitivityNo data available
Description (Association (MCS))Solvent (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))Stability constant of the complex with ...CCl424.94-FluorophenolStability constant of the complex with ... aq. HNO325AgNO3Enthalpy of associationacetonitrile25iodineNMR spectrum of the complexCDCl3Cu(2,4-dichloro-benzoate)2
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Comment (NMR Spectroscopy) Chemical shifts1Htetradeuteriomethanol Chemical shifts13Ctetradeuteriomethanol Spin-spin coupling constants tetradeuteriomethanol 1H-1H.
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1Absorption maximamethanol 27615
Route-of-Synthesis-ROS-of-Pneumocandin-B0-CAS-135575-42-7
ConditionsYieldWith trifluoroacetic acid; phenylboronic acid In acetonitrile at -50 - -45â; for 2.5h; Inert atmosphere;
Experimental Procedure
Under nitrogen gas protection, acetonitrile (100 ml), the compound of formula (2) (5.0 g), phenylboronic acid (0.90 g) and 3-mercaptophenol (1.80 g) were uniformly stirred and the temperature was raised to -50 to -45°C And trifluoroacetic acid (1.05 ml) was added dropwise. After the dropwise addition, the mixture was reacted at -50 to -45°C for about 2.5 hours. After confirming the completion of the reaction by TLC monitoring, the reaction was stopped and an aqueous solution of NaOAc (1.15 g NaOAc dissolved in 25 ml of water) was added slowly, and the temperature was raised to 20 ° C and stirred for 2 hours. A large amount of solid was precipitated, the temperature was lowered to 0 ° C or lower, and the filtrate was subjected to third washing with 60 ml of acetonitrile / water = 9: 1 (V / V), followed by vacuum drying for 5 hours, 3b (4.65 g, yield 93%). 93%With trifluorormethanesulfonic acid; phenylboronic acid In acetonitrile at -50 - -45â; for 2.5h; Inert atmosphere;0.27
SignalDangerGHS Hazard StatementsH315 (92.31%): Causes skin irritation
H317 (15.38%): May cause an allergic skin reaction
H318 (92.31%): Causes serious eye damage
H334 (15.38%): May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335 (15.38%): May cause respiratory irritation
H400 (92.31%): Very toxic to aquatic life
Information may vary between notifications depending on impurities, additives, and other factors. Precautionary Statement CodesP261, P264, P271, P272, P273, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P310, P312, P321, P332+P313, P333+P313, P342+P311, P362, P363, P391, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)
TransportationNot dangerous goodsUnder the room temperature and away from lightHS Code294200StorageUnder the room temperature and away from lightShelf Life1 yearMarket PriceUSD
DruglikenessLipinski rules componentMolecular Weight1065.23 logP3.701 HBA24 HBD15 Matching Lipinski Rules1Veber rules componentPolar Surface Area (PSA)411.28 Rotatable Bond (RotB)21Matching Veber Rules0
BioactivityIn vitro: EfficacyQuantitative Results
pXParameterValue (qual)Value (quant)UnitBiological Species TargetBioassayEffect7.25MFC (minimum fungicidal concentration)(Antifungal activity) =0.06”g/mL Candida tropicalis 7.15IC50 70nM In Vitro (others) antifungal agent 7.15 IC50 =0.07”MCandida albicans Inhibitor 7.15IC50(Beta-(1,3)-D-glucan synthesis) =70nM Candida albicans MY1208 Inhibitor6.95MFC (minimum fungicidal concentration)(Minimum Inhibitory Concentration) =0.12”g/mL Candida tropicalis MY1012 6.63MFC (minimum fungicidal concentration) =0.25Όg/mlCandida albicans 6.63MFC (minimum fungicidal concentration) =0.25Όg/mlCandida albicans MY1208 6.63MFC (minimum fungicidal concentration)(Minimum Inhibitory Concentration) =0.5Όg/ml Candida albicans MY1055 6.03MFC (minimum fungicidal concentration)=1Όg/mlKluyveromyces marxianus MY2099 5.73MFC (minimum fungicidal concentration)(Minimum Inhibitory Concentration) =2”g/mL Candida parapsilosis MY1010 5.42MFC (minimum fungicidal concentration)(Antifungal activity) =4”g/mL Candida parapsilosis4.69IC50 20.23 ”M In Vitro (others)3.92MIC 128 mg/L In Vitro (others) fungistatic agent ZI (zone of inhibition) 8mmIn Vitro (others) fungistatic agent MED99.9(Reduction (99.9%) of viable CFUs recoverable from mouse kidneys infected with Candida albicans (MY1208)) =6mg/kgmouse
Quantitative Results1 of 9Effectfungistatic agent Biological material Aspergillus fumigatus Assay Description Bioassay : 35 deg C; potato dextrose agar 16 clinical strains (MF5668, CLY315, CLY522, CLY523 among them); in vitro; agar dilution diffusion method (Acar, J.F. 1986. Disk susceptibility test, p. 27-63. In V. Lorian (ed.) Antibiotics in laboratory medicine); 1.2E5 CFU/ml inoculum Results critical concentration, CC 0.03 - 0.05 mg/l 2 of 9 Effect Hemolytic Assay Description Target : CD-1 mouse whole blood
Bioassay : unwashed erythrocyte hemolysis assay; room temperature Results MLC, minimum lytic concentration active 3.13 mg/l 3 of 9Effect Hemolytic Biological material human Assay Description Bioassay : unwashed erythrocyte hemolysis assay; room temperature Results MLC, minimum lytic concentration active 25 mg/l 4 of 9Effect antifungal agent Assay Description Target : Candida albicans MY1055
Bioassay : time-killing assay Results time-kill curve; fungicide 5 of 9Results glucan synthesis inhibition in a Candida albicans membrane assay: IC50 = 0.07 ΌM 6 of 9Effect fungistatic agent Assay Description Target : Aspergillus fumigatus H11-20
Bioassay : in vitro; agar diffusion assay; potato dextrose agar; 1E6 conidia/petri dish inoculum; 30 deg C; zone of inhibition measured Results critical conc. 7 of 9Effect fungistatic agent Assay DescriptionEffect : eye observable change in morphology
Target : Aspergillus fumigatus H11-20
Bioassay : in vitro; broth microdilution assay; Yeast Nitrogen Base with 2 percent glucose; 1E4 condidia/well inoculum; 30 deg C Resultsmin. effective conc., MEC 0.5 mg/l 8 of 9EffectAntifungal activity against Candida albicans, Candida tropicalis, Candida parapsilosis, Candida pseudotropicalis 9 of 9Results TOKA ED99.9 = 6 mg/kg
Toxicity/Safety PharmacologyQuantitative Results
pXParameterValue (quant)UnitBiological Species Bioassay Effect7.58MFC90 0.25mg/L Candida albicans Cell/tumor cell: proliferation/viability/growth antifungal agent 7.28MFC90 0.5mg/L Candida tropicalis Cell/tumor cell: proliferation/viability/growth antifungal agent 6.95MFC (minimum fungicidal concentration) 0.12 - 0.5mg/L Candida albicans Cell/tumor cell: proliferation/viability/growth antifungal agent 6.68MFC90 2mg/L Candida glabrata Cell/tumor cell: proliferation/viability/growth antifungal agent 6.63MFC (minimum fungicidal concentration) 0.25 - 2mg/L Candida glabrata Cell/tumor cell: proliferation/viability/growth antifungal agent 6.33MFC (minimum fungicidal concentration) 0.5 - 64 mg/LCryptococcus neoformansCell/tumor cell: proliferation/viability/growthantifungal agent 6.03MFC50 1mg/L Kluyveromyces marxianus Cell/tumor cell: proliferation/viability/growth antifungal agent 5.73MFC50 2mg/L Pichia kudriavzevii Cell/tumor cell: proliferation/viability/growth antifungal agent 5.42MFC (minimum fungicidal concentration) 4-128mg/L Meyerozyma guilliermondii Cell/tumor cell: proliferation/viability/growth antifungal agent 5.18MFC9064mg/L Meyerozyma guilliermondii Cell/tumor cell: proliferation/viability/growth antifungal agent 5.12MFC (minimum fungicidal concentration) 8mg/L Clavispora lusitaniae Cell/tumor cell: proliferation/viability/growth antifungal agent 4.88MIC90 128mg/L Aspergillus niger Cell/tumor cell: proliferation/viability/growth antifungal agent 3.92MIC 128mg/L Aspergillus flavus Cell/tumor cell: proliferation/viability/growth antifungal agent
Use PatternPneumocandin B0 CAS 135575-42-7 is starting material for production of antifungal cyclohexapeptide compounds. Pneumocandin B0 CAS 135575-42-7 is used as the pharmaceutical intermediates of the Caspofungin which is a lyophilized preparation.
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