Standard Article

Lanthanide Enolates as Nuclear Magnetic Resonance Shift Reagents

Metal Enolates (2009)

  1. Thomas J. Wenzel,
  2. Katelyn A. Provencher

Published Online: 15 SEP 2010

DOI: 10.1002/9780470682531.pat0430

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Wenzel, T. J. and Provencher, K. A. 2010. Lanthanide Enolates as Nuclear Magnetic Resonance Shift Reagents. Patai's Chemistry of Functional Groups. .

Author Information

  1. Bates College, Department of Chemistry, Lewiston, Maine, USA

Publication History

  1. Published Online: 15 SEP 2010

Featured Compounds

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  1. 1 - 91
Compound 1
Drug synonym:Not Available
Molecular Weight:184.2753
Molecular Formula:C11H20O2
SMILES:CC(C)(C)C(=O)CC(=O)C(C)(C)C
InChI:1S/C11H20O2/c1-10(2,3)8(12)7-9(13)11(4,5)6/h7H2,1-6H3
InChIKey:YRAJNWYBUCUFBD-UHFFFAOYSA-N
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Compound 2
Drug synonym:Not Available
Molecular Weight:296.182
Molecular Formula:C10H11F7O2
SMILES:CC(C)(C)C(=O)CC(=O)C(F)(F)C(F)(F)C(F)(F)F
InChI:1S/C10H11F7O2/c1-7(2,3)5(18)4-6(19)8(11,12)9(13,14)10(15,16)17/h4H2,1-3H3
InChIKey:SQNZLBOJCWQLGQ-UHFFFAOYSA-N
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Compound 3
Drug synonym:Not Available
Molecular Weight:204.243
Molecular Formula:C9H18NO4
SMILES:CC(=O)OC(CC(O)=O)C[N+](C)(C)C
InChI:1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/p+1
InChIKey:RDHQFKQIGNGIED-UHFFFAOYSA-O
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Compound 4
Drug synonym:Not Available
Molecular Weight:170.2487
Molecular Formula:C10H18O2
SMILES:[H][C@]12CO[C@](CC)(O1)[C@@]([H])(C)C[C@@]2([H])C
InChI:1S/C10H18O2/c1-4-10-8(3)5-7(2)9(12-10)6-11-10/h7-9H,4-6H2,1-3H3/t7-,8+,9-,10-/m1/s1
InChIKey:YMBRJMLOGNZRFY-UTINFBMNSA-N
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Compound 4'
Drug synonym:Not Available
Molecular Weight:175.227
Molecular Formula:C11H13NO
SMILES:CCC1(CNC1=O)c1ccccc1
InChI:1S/C11H13NO/c1-2-11(8-12-10(11)13)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3,(H,12,13)
InChIKey:QKXTXXKOSUMTNX-UHFFFAOYSA-N
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Compound 4''
Drug synonym:Not Available
Molecular Weight:111.1418
Molecular Formula:C6H9NO
SMILES:O=C1NC2CCCC12
InChI:1S/C6H9NO/c8-6-4-2-1-3-5(4)7-6/h4-5H,1-3H2,(H,7,8)
InChIKey:AXDBIGNYXNSBHV-UHFFFAOYSA-N
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Compound 5
Drug synonym:Not Available
Molecular Weight:217.2637
Molecular Formula:C13H15NO2
SMILES:COC1NC(=O)CC2CC1c1ccccc21
InChI:1S/C13H15NO2/c1-16-13-11-6-8(7-12(15)14-13)9-4-2-3-5-10(9)11/h2-5,8,11,13H,6-7H2,1H3,(H,14,15)
InChIKey:CPUNSUBDQUBQHZ-UHFFFAOYSA-N
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Compound 6
Drug synonym:Not Available
Molecular Weight:282.4198
Molecular Formula:C20H26O
SMILES:CC1(C)CC(C)(O)C[C@@](C)(C1)c1cccc2ccccc12
InChI:1S/C20H26O/c1-18(2)12-19(3,14-20(4,21)13-18)17-11-7-9-15-8-5-6-10-16(15)17/h5-11,21H,12-14H2,1-4H3/t19-,20?/m1/s1
InChIKey:LDLCBRKARDCJLI-FIWHBWSRSA-N
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Compound 7
Drug synonym:Not Available
Molecular Weight:398.5781
Molecular Formula:C26H38O3
SMILES:CC1(C)CCCC2(C)C1CCC1(C)C2CC[C@@]2(C)[C@@H](OC(=O)CC12)c1ccoc1
InChI:1S/C26H38O3/c1-23(2)10-6-11-24(3)18(23)7-12-25(4)19(24)8-13-26(5)20(25)15-21(27)29-22(26)17-9-14-28-16-17/h9,14,16,18-20,22H,6-8,10-13,15H2,1-5H3/t18?,19?,20?,22-,24?,25?,26+/m0/s1
InChIKey:UDHQRLHLHLDBHV-FMLDVPITSA-N
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Compound 8
Drug synonym:Not Available
Molecular Weight:195.3012
Molecular Formula:C12H21NO
SMILES:CC(C)(C)\C=C\C1=[N+]([O-])C(C)(C)CC1
InChI:1S/C12H21NO/c1-11(2,3)8-6-10-7-9-12(4,5)13(10)14/h6,8H,7,9H2,1-5H3/b8-6+
InChIKey:VBUNAYIXLYYUIE-SOFGYWHQSA-N
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Compound 9
Drug synonym:Not Available
Molecular Weight:446.966
Molecular Formula:C13H20EuN2NiO2
SMILES:[Eu+3].CC1CN([Ni]N1\C(C)=C/C(C)=O)C(\C)=C/C(C)=O
InChI:1S/C13H22N2O2.Eu.Ni/c1-9(6-12(4)16)14-8-11(3)15-10(2)7-13(5)17;;/h6-7,11H,8H2,1-5H3,(H2,14,15,16,17);;/q;+3;+2/p-2
InChIKey:HCVKRRNUZUAMOV-UHFFFAOYSA-L
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Compound 10
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 11
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 12
Drug synonym:Not Available
Molecular Weight:162.25
Molecular Formula:C7H14O2S
SMILES:C[C@H]1C[C@@H](C)CS(=O)(=O)C1
InChI:1S/C7H14O2S/c1-6-3-7(2)5-10(8,9)4-6/h6-7H,3-5H2,1-2H3/t6-,7+
InChIKey:SAGOAKDWIVKDTC-KNVOCYPGSA-N
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Compound 13
Drug synonym:Not Available
Molecular Weight:1171.64
Molecular Formula:C34H36EuF21O9S
SMILES:[Eu+3].O=S1(=O)CC2OC2C1.CC(C)(C)C(\[O-])=C\C(=O)C(F)(F)C(F)(F)C(F)(F)F.CC(C)(C)C(\[O-])=C\C(=O)C(F)(F)C(F)(F)C(F)(F)F.CC(C)(C)C(\[O-])=C\C(=O)C(F)(F)C(F)(F)C(F)(F)F
InChI:1S/3C10H11F7O2.C4H6O3S.Eu/c3*1-7(2,3)5(18)4-6(19)8(11,12)9(13,14)10(15,16)17;5-8(6)1-3-4(2-8)7-3;/h3*4,18H,1-3H3;3-4H,1-2H2;/q;;;;+3/p-3/b3*5-4-;;
InChIKey:UKIXHKOEYNVAMA-BSWAEIBTSA-K
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Compound 14
Drug synonym:Not Available
Molecular Weight:174.261
Molecular Formula:C8H14O2S
SMILES:O=S1(=O)CCCC2CCCC12
InChI:1S/C8H14O2S/c9-11(10)6-2-4-7-3-1-5-8(7)11/h7-8H,1-6H2
InChIKey:HTEGRJFXZVNSLI-UHFFFAOYSA-N
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Compound 15
Drug synonym:Not Available
Molecular Weight:174.261
Molecular Formula:C8H14O2S
SMILES:O=S1(=O)CC2CCCCC2C1
InChI:1S/C8H14O2S/c9-11(10)5-7-3-1-2-4-8(7)6-11/h7-8H,1-6H2
InChIKey:VGQCRPHTIKWVRB-UHFFFAOYSA-N
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Compound 16
Drug synonym:Not Available
Molecular Weight:550.7766
Molecular Formula:C36H46N4O
SMILES:CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)C(=O)C4(CC)CC)c(CC)c3CC
InChI:1S/C36H46N4O/c1-9-21-22(10-2)28-18-30-25(13-5)26(14-6)32(39-30)20-34-36(15-7,16-8)35(41)33(40-34)19-31-24(12-4)23(11-3)29(38-31)17-27(21)37-28/h17-20,38-39H,9-16H2,1-8H3/b27-17-,28-18-,29-17-,30-18-,31-19-,32-20-,33-19-,34-20-
InChIKey:FIDRNDANECZKGX-IZOYJUGISA-N
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Compound 17
Drug synonym:Not Available
Molecular Weight:196.3291
Molecular Formula:C13H24O
SMILES:CCCCCC#CCCCCCCO
InChI:1S/C13H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14/h14H,2-5,8-13H2,1H3
InChIKey:FCXURDQZLWYZFL-UHFFFAOYSA-N
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Compound 18
Drug synonym:Not Available
Molecular Weight:140.2227
Molecular Formula:C9H16O
SMILES:CC1(C)C2CC1C(O)CC2
InChI:1S/C9H16O/c1-9(2)6-3-4-8(10)7(9)5-6/h6-8,10H,3-5H2,1-2H3
InChIKey:DEDZBEBBIUTZAJ-UHFFFAOYSA-N
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Compound 18'
Drug synonym:Not Available
Molecular Weight:141.2289
Molecular Formula:C9H16O
SMILES:[2H]C1(O)CCC2CC1C2(C)C
InChI:Not Available
InChIKey:Not Available
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Compound 19
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:(C8H8O)nC16H18O2
SMILES:Cc1cc(Oc2c(C)cc(Oc3c(C)cccc3C)cc2C)cc(C)c1O
InChI:1S/C24H26O3/c1-14-8-7-9-15(2)23(14)26-21-12-18(5)24(19(6)13-21)27-20-10-16(3)22(25)17(4)11-20/h7-13,25H,1-6H3
InChIKey:IBOWKGBARGTQCG-UHFFFAOYSA-N
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Compound 20
Drug synonym:Not Available
Molecular Weight:460.5183
Molecular Formula:Not Available
SMILES:CC(C)(CO*)COC(=O)c1ccc(cc1)C(=O)Oc1ccc(cc1)C(C)(C)c1ccc(O*)cc1
InChI:Not Available
InChIKey:Not Available
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Compound 21
Drug synonym:Not Available
Molecular Weight:850.8622
Molecular Formula:Not Available
SMILES:Cc1cc(ccc1O*)C(C)(C)c1ccc(OC(=O)c2ccc(cc2)C(=O)Oc2ccc(cc2)C2(OC(=O)c3ccccc23)c2ccc(OC(=O)c3ccc(cc3)C(=O)O*)cc2)c(C)c1
InChI:Not Available
InChIKey:Not Available
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Compound 22
Drug synonym:Not Available
Molecular Weight:518.997
Molecular Formula:C25H34ClF3N2O4
SMILES:[O-][Cl](=O)(=O)=O.CCCCCN(CCCCC)c1ccc(\C=C\c2cc[n+](CC(F)(F)F)cc2)cc1
InChI:1S/C25H34F3N2.ClHO4/c1-3-5-7-17-30(18-8-6-4-2)24-13-11-22(12-14-24)9-10-23-15-19-29(20-16-23)21-25(26,27)28;2-1(3,4)5/h9-16,19-20H,3-8,17-18,21H2,1-2H3;(H,2,3,4,5)/q+1;/p-1
InChIKey:TZHMOKUTVZFBHU-UHFFFAOYSA-M
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Compound 23
Drug synonym:Not Available
Molecular Weight:786.1134
Molecular Formula:C44H84NO8P
SMILES:CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI:1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-
InChIKey:SNKAWJBJQDLSFF-YEUCEMRASA-N
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Compound 23'
Drug synonym:Not Available
Molecular Weight:846.2515
Molecular Formula:C48H96NO8P
SMILES:CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC(C)CCCC(C)CCCC(C)CCCC(C)C
InChI:1S/C48H96NO8P/c1-38(2)20-14-22-40(5)24-16-26-42(7)28-18-30-44(9)34-47(50)54-36-46(37-56-58(52,53)55-33-32-49(11,12)13)57-48(51)35-45(10)31-19-29-43(8)27-17-25-41(6)23-15-21-39(3)4/h38-46H,14-37H2,1-13H3
InChIKey:UKDDQGWMHWQMBI-UHFFFAOYSA-N
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Compound 24
Drug synonym:Not Available
Molecular Weight:204.2649
Molecular Formula:C13H16O2
SMILES:COC(=O)c1ccc(C)cc1C=C(C)C
InChI:1S/C13H16O2/c1-9(2)7-11-8-10(3)5-6-12(11)13(14)15-4/h5-8H,1-4H3
InChIKey:BVZJUBXUZBTZGD-UHFFFAOYSA-N
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Compound 24'
Drug synonym:Not Available
Molecular Weight:176.2548
Molecular Formula:C12H16O
SMILES:CC(C)=Cc1cc(C)ccc1CO
InChI:1S/C12H16O/c1-9(2)6-12-7-10(3)4-5-11(12)8-13/h4-7,13H,8H2,1-3H3
InChIKey:KHQHVWKARBKUCT-UHFFFAOYSA-N
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Compound 25
Drug synonym:Not Available
Molecular Weight:353.3273
Molecular Formula:C15H19N3O7
SMILES:CCOC(=O)C(CC(C)C)NC(=O)c1cc(cc(c1)[N+]([O-])=O)[N+]([O-])=O
InChI:1S/C15H19N3O7/c1-4-25-15(20)13(5-9(2)3)16-14(19)10-6-11(17(21)22)8-12(7-10)18(23)24/h6-9,13H,4-5H2,1-3H3,(H,16,19)
InChIKey:SPVZUYZZIIOZRM-UHFFFAOYSA-N
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Compound 26
Drug synonym:Not Available
Molecular Weight:267.2464
Molecular Formula:C14H12F3NO
SMILES:CC(NC(=O)C(F)(F)F)c1cccc2ccccc12
InChI:1S/C14H12F3NO/c1-9(18-13(19)14(15,16)17)11-8-4-6-10-5-2-3-7-12(10)11/h2-9H,1H3,(H,18,19)
InChIKey:NOJXWADZEDSEGP-UHFFFAOYSA-N
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Compound 27
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 28
Drug synonym:Not Available
Molecular Weight:236.3499
Molecular Formula:C15H24O2
SMILES:CC(C)(C)C(=O)C1C2CCC(C)(C1=O)C2(C)C
InChI:1S/C15H24O2/c1-13(2,3)11(16)10-9-7-8-15(6,12(10)17)14(9,4)5/h9-10H,7-8H2,1-6H3
InChIKey:DOOCADGKJPCQSD-UHFFFAOYSA-N
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Compound 29
Drug synonym:Not Available
Molecular Weight:248.2415
Molecular Formula:C12H15F3O2
SMILES:CC1(C)C2CCC1(C)C(=O)C2C(=O)C(F)(F)F
InChI:1S/C12H15F3O2/c1-10(2)6-4-5-11(10,3)8(16)7(6)9(17)12(13,14)15/h6-7H,4-5H2,1-3H3
InChIKey:ISLOIHOAZDSEAJ-UHFFFAOYSA-N
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Compound 30
Drug synonym:Not Available
Molecular Weight:348.2565
Molecular Formula:C14H15F7O2
SMILES:CC1(C)C2CCC1(C)C(=O)C2C(=O)C(F)(F)C(F)(F)C(F)(F)F
InChI:1S/C14H15F7O2/c1-10(2)6-4-5-11(10,3)8(22)7(6)9(23)12(15,16)13(17,18)14(19,20)21/h6-7H,4-5H2,1-3H3
InChIKey:PEWOESYEGLBLNR-UHFFFAOYSA-N
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Compound 31
Drug synonym:Not Available
Molecular Weight:320.5093
Molecular Formula:C21H36O2
SMILES:CC1CCC(C)(C(=O)CC(=O)C2(C)CCC(C)C2(C)C)C1(C)C
InChI:1S/C21H36O2/c1-14-9-11-20(7,18(14,3)4)16(22)13-17(23)21(8)12-10-15(2)19(21,5)6/h14-15H,9-13H2,1-8H3
InChIKey:ZCXWUWQWHMZXOK-UHFFFAOYSA-N
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Compound 32
Drug synonym:Not Available
Molecular Weight:380.909
Molecular Formula:C12H8Cl6O
SMILES:ClC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl
InChI:1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2
InChIKey:DFBKLUNHFCTMDC-UHFFFAOYSA-N
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Compound 32'
Drug synonym:Not Available
Molecular Weight:398.925
Molecular Formula:C12H10Cl6O2
SMILES:O[C@H]1[C@@H](O)C2CC1C1C2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl
InChI:1S/C12H10Cl6O2/c13-8-9(14)11(16)5-3-1-2(6(19)7(3)20)4(5)10(8,15)12(11,17)18/h2-7,19-20H,1H2/t2?,3?,4?,5?,6-,7+,10?,11?
InChIKey:NWRDBJRTQVHAKR-ARMUGHSSSA-N
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Compound 32''
Drug synonym:Not Available
Molecular Weight:398.925
Molecular Formula:C12H10Cl6O2
SMILES:O[C@@H]1[C@@H](O)C2CC1C1C2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl
InChI:1S/C12H10Cl6O2/c13-8-9(14)11(16)5-3-1-2(6(19)7(3)20)4(5)10(8,15)12(11,17)18/h2-7,19-20H,1H2/t2?,3?,4?,5?,6-,7-,10?,11?/m0/s1
InChIKey:NWRDBJRTQVHAKR-JYGFWBPPSA-N
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Compound 33
Drug synonym:2‐phenylethanol, benzeneethanol, phenethanol, phenethyl alcohol, phenylethyl alcohol
Molecular Weight:122.1644
Molecular Formula:C8H10O
SMILES:OCCC1=CC=CC=C1
InChI:1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
InChIKey:WRMNZCZEMHIOCP-UHFFFAOYSA-N
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Compound 34
Drug synonym:Not Available
Molecular Weight:105.1932
Molecular Formula:C6H14O
SMILES:[2H]C([2H])([2H])C(C)(CC)CO
InChI:Not Available
InChIKey:Not Available
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Compound 35
Drug synonym:Not Available
Molecular Weight:189.2646
Molecular Formula:C13H12O
SMILES:[2H]c1c([2H])c([2H])c(C(O)c2ccccc2)c([2H])c1[2H]
InChI:Not Available
InChIKey:Not Available
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Compound 36
Drug synonym:Not Available
Molecular Weight:260.194
Molecular Formula:C10H14BrNS
SMILES:[Br-].CS\C=[N+](/C)Cc1ccccc1
InChI:1S/C10H14NS.BrH/c1-11(9-12-2)8-10-6-4-3-5-7-10;/h3-7,9H,8H2,1-2H3;1H/q+1;/p-1/b11-9+;
InChIKey:FKRDVSURONWYBY-LBEJWNQZSA-M
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Compound 37
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 37a
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 37b
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 37c
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 38
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 39
Drug synonym:Not Available
Molecular Weight:156.136
Molecular Formula:C7H8O4
SMILES:COC(=O)CC#CC(=O)OC
InChI:1S/C7H8O4/c1-10-6(8)4-3-5-7(9)11-2/h4H2,1-2H3
InChIKey:DDSKZCDBPUQSPS-UHFFFAOYSA-N
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Compound 40
Drug synonym:Not Available
Molecular Weight:427.4486
Molecular Formula:C26H21NO5
SMILES:COC(=O)C(\[O-])=C(/C(=O)OC)[n+]1c(-c2ccccc2C)c2ccccc2c2ccccc12
InChI:1S/C26H21NO5/c1-16-10-4-5-11-17(16)22-20-14-7-6-12-18(20)19-13-8-9-15-21(19)27(22)23(25(29)31-2)24(28)26(30)32-3/h4-15H,1-3H3
InChIKey:BMVTUSNRUSZUCK-UHFFFAOYSA-N
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Compound 41
Drug synonym:Not Available
Molecular Weight:226.2689
Molecular Formula:C12H18O4
SMILES:COC(=O)C(C)C(=C)C(=C)C(C)C(=O)OC
InChI:1S/C12H18O4/c1-7(9(3)11(13)15-5)8(2)10(4)12(14)16-6/h9-10H,1-2H2,3-6H3
InChIKey:NIUBPGCIIPVPHK-UHFFFAOYSA-N
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Compound 42
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 43
Drug synonym:Not Available
Molecular Weight:184.0674
Molecular Formula:C7H9AsO
SMILES:Not Available
InChI:1S/C7H9AsO/c1-8(9)7-5-3-2-4-6-7/h2-6,9H,1H3
InChIKey:MHHKHJTUALDMPG-UHFFFAOYSA-N
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Compound 44a
Drug synonym:Not Available
Molecular Weight:416.5104
Molecular Formula:C30H24O2
SMILES:CC1=CC2C(C=C1)C(=O)c1ccccc1C2C1c2ccccc2C(=O)c2ccc(C)cc12
InChI:1S/C30H24O2/c1-17-11-13-23-25(15-17)27(19-7-3-5-9-21(19)29(23)31)28-20-8-4-6-10-22(20)30(32)24-14-12-18(2)16-26(24)28/h3-16,23,25,27-28H,1-2H3
InChIKey:MABZBHQYVLPDLK-UHFFFAOYSA-N
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Compound 44b
Drug synonym:Not Available
Molecular Weight:416.5104
Molecular Formula:C30H24O2
SMILES:CC1=CC2C(C=C1)C(C1c3ccccc3C(=O)c3cc(C)ccc13)c1ccccc1C2=O
InChI:1S/C30H24O2/c1-17-11-13-21-25(15-17)29(31)23-9-5-3-7-19(23)27(21)28-20-8-4-6-10-24(20)30(32)26-16-18(2)12-14-22(26)28/h3-16,21,25,27-28H,1-2H3
InChIKey:CAEAVANGQNZJAL-UHFFFAOYSA-N
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Compound 45
Drug synonym:Not Available
Molecular Weight:182.2179
Molecular Formula:C13H10O
SMILES:O=C1\C=C/C=C\c2ccccc2/C=C\1
InChI:1S/C13H10O/c14-13-8-4-3-6-11-5-1-2-7-12(11)9-10-13/h1-10H/b6-3-,8-4-,10-9-
InChIKey:MTIPEROSCIMKOK-TWSJNVEOSA-N
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Compound 44
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 46
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 46a
Drug synonym:Not Available
Molecular Weight:330.3319
Molecular Formula:C18H18O6
SMILES:COC(=O)c1cccc(OC)c1-c1c(OC)cccc1C(=O)OC
InChI:1S/C18H18O6/c1-21-13-9-5-7-11(17(19)23-3)15(13)16-12(18(20)24-4)8-6-10-14(16)22-2/h5-10H,1-4H3
InChIKey:AWZIUZBNCBHQTI-UHFFFAOYSA-N
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Compound 46b
Drug synonym:Not Available
Molecular Weight:360.2751
Molecular Formula:C16H12N2O8
SMILES:COC(=O)c1cccc(c1-c1c(cccc1[N+]([O-])=O)C(=O)OC)[N+]([O-])=O
InChI:1S/C16H12N2O8/c1-25-15(19)9-5-3-7-11(17(21)22)13(9)14-10(16(20)26-2)6-4-8-12(14)18(23)24/h3-8H,1-2H3
InChIKey:VWKXXMPVBIQLRJ-UHFFFAOYSA-N
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Compound 46c
Drug synonym:Not Available
Molecular Weight:302.2788
Molecular Formula:C16H14O6
SMILES:COc1cccc(C(O)=O)c1-c1c(OC)cccc1C(O)=O
InChI:1S/C16H14O6/c1-21-11-7-3-5-9(15(17)18)13(11)14-10(16(19)20)6-4-8-12(14)22-2/h3-8H,1-2H3,(H,17,18)(H,19,20)
InChIKey:XWHPDXLPTVOKAK-UHFFFAOYSA-N
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Compound 47
Drug synonym:Not Available
Molecular Weight:894.9994
Molecular Formula:C54H54O12
SMILES:COC1=CC2=C3CC4=CC(OC)=C5OCCOC6=CC7=C(CC8=C(CC9=C(C7)C=C(OC)C(OCCOC1=C3)=C9)C=C(OC)C(OCCOC1=C(OC)C=C(CC4=C5)C(C2)=C1)=C8)C=C6OC
InChI:1S/C54H54O12/c1-55-43-19-31-13-38-26-50-45(57-3)21-33(38)15-39-27-52-44(56-2)20-32(39)14-37(31)25-49(43)61-7-8-62-51-28-40-16-35-23-47(59-5)53(65-10-9-63-50)30-42(35)18-36-24-48(60-6)54(66-12-11-64-52)29-41(36)17-34(40)22-46(51)58-4/h19-30H,7-18H2,1-6H3
InChIKey:SQMLCHVWDQRDTG-UHFFFAOYSA-N
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Compound 48
Drug synonym:Not Available
Molecular Weight:661.0498
Molecular Formula:C42H76O5
SMILES:CC(C)=CCC[C@@](C)(O)CCC[C@@](C)(O)CCC[C@@](C)(O)CCC[C@@](C)(O)CCC\C(C)=C\C\C(C)=C\C\C(C)=C\C\C(C)=C\CO
InChI:1S/C42H76O5/c1-34(2)16-11-25-39(7,44)27-13-29-41(9,46)31-15-32-42(10,47)30-14-28-40(8,45)26-12-17-35(3)18-19-36(4)20-21-37(5)22-23-38(6)24-33-43/h16,18,20,22,24,43-47H,11-15,17,19,21,23,25-33H2,1-10H3/b35-18+,36-20+,37-22+,38-24+/t39-,40+,41-,42+/m1/s1
InChIKey:HJORWPXAILIBRL-FTJRLTLYSA-N
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Compound 49
Drug synonym:dipentene, limonene
Molecular Weight:136.234
Molecular Formula:C10H16
SMILES:CC(=C)C1CCC(C)=CC1
InChI:Not Available
InChIKey:Not Available
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Compound 50
Drug synonym:Not Available
Molecular Weight:136.234
Molecular Formula:C10H16
SMILES:CC1(C)C2CC1C(=C)CC2
InChI:Not Available
InChIKey:Not Available
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Compound 51
Drug synonym:2,2‐dimethyl‐3‐methylenenorbornane, camphene
Molecular Weight:136.234
Molecular Formula:C10H16
SMILES:CC1(C)C2CCC(C2)C1=C
InChI:1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3
InChIKey:CRPUJAZIXJMDBK-UHFFFAOYSA-N
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Compound 52
Drug synonym:Not Available
Molecular Weight:136.234
Molecular Formula:C10H16
SMILES:CC1=CCC2CC1C2(C)C
InChI:1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3
InChIKey:GRWFGVWFFZKLTI-UHFFFAOYSA-N
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Compound 53
Drug synonym:Not Available
Molecular Weight:136.234
Molecular Formula:C10H16
SMILES:CC1=CCC2C(C1)C2(C)C
InChI:1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3
InChIKey:BQOFWKZOCNGFEC-UHFFFAOYSA-N
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Compound 54
Drug synonym:Not Available
Molecular Weight:204.3511
Molecular Formula:C15H24
SMILES:CC(C)=CCCC1(C)C2CCC(C2)C1=C
InChI:1S/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3
InChIKey:PGBNIHXXFQBCPU-UHFFFAOYSA-N
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Compound 55
Drug synonym:Not Available
Molecular Weight:204.3511
Molecular Formula:C15H24
SMILES:CC(C)C1CCC2(C)C3CC=C(C)C2C13
InChI:1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3
InChIKey:VLXDPFLIRFYIME-UHFFFAOYSA-N
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Compound 56
Drug synonym:Not Available
Molecular Weight:516.7138
Molecular Formula:C40H36
SMILES:C(C1C(Cc2ccccc2)\C(=C\c2ccccc2)C(Cc2ccccc2)=C1Cc1ccccc1)c1ccccc1
InChI:1S/C40H36/c1-6-16-31(17-7-1)26-36-37(27-32-18-8-2-9-19-32)39(29-34-22-12-4-13-23-34)40(30-35-24-14-5-15-25-35)38(36)28-33-20-10-3-11-21-33/h1-26,37,39H,27-30H2/b36-26-
InChIKey:ZJMQXQWYDHAKIH-QYVLQNAGSA-N
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Compound 57
Drug synonym:Not Available
Molecular Weight:136.234
Molecular Formula:C10H16
SMILES:CC(C)=CCCC(=C)C=C
InChI:1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3
InChIKey:UAHWPYUMFXYFJY-UHFFFAOYSA-N
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Compound 58
Drug synonym:Not Available
Molecular Weight:346.6327
Molecular Formula:C25H46
SMILES:CC(C)CCC\C(C)=C\C[C@@H](CCC(C)C=C)C(=C)CCCC(C)C
InChI:1S/C25H46/c1-9-22(6)16-18-25(24(8)15-11-13-21(4)5)19-17-23(7)14-10-12-20(2)3/h9,17,20-22,25H,1,8,10-16,18-19H2,2-7H3/b23-17+/t22?,25-/m1/s1
InChIKey:BSXYLMVBPPIDSG-WTFFSMHXSA-N
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Compound 59
Drug synonym:Not Available
Molecular Weight:158.2396
Molecular Formula:C12H14
SMILES:CC#CC(C)Cc1ccccc1
InChI:1S/C12H14/c1-3-7-11(2)10-12-8-5-4-6-9-12/h4-6,8-9,11H,10H2,1-2H3
InChIKey:GZVSTTLZDWCOIS-UHFFFAOYSA-N
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Compound 60
Drug synonym:Not Available
Molecular Weight:216.3187
Molecular Formula:C15H20O
SMILES:Cc1coc2CC(C)=CCC\C(C)=C\Cc12
InChI:1S/C15H20O/c1-11-5-4-6-12(2)9-15-14(8-7-11)13(3)10-16-15/h6-7,10H,4-5,8-9H2,1-3H3/b11-7+,12-6-
InChIKey:VMDXHYHOJPKFEK-RZWYOFBOSA-N
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Compound 61
Drug synonym:Not Available
Molecular Weight:234.3355
Molecular Formula:C18H18
SMILES:CC1=CC=C2C=CC3=C(C(C)=C(C)C=C3)C2=C1C
InChI:1S/C18H18/c1-11-5-7-15-9-10-16-8-6-12(2)14(4)18(16)17(15)13(11)3/h5-10H,1-4H3
InChIKey:BUSLHLOSCTVNRQ-UHFFFAOYSA-N
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Compound 62
Drug synonym:Not Available
Molecular Weight:360.849
Molecular Formula:C7H8Br2Cl2F2
SMILES:C[C@@H](Br)C1(Br)[C@@H](C)C(Cl)(Cl)C1(F)F
InChI:1S/C7H8Br2Cl2F2/c1-3-5(9,4(2)8)7(12,13)6(3,10)11/h3-4H,1-2H3/t3-,4-,5?/m1/s1
InChIKey:ZWHYQCPFCXWSOH-ZZKAVYKESA-N
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Compound 63
Drug synonym:Not Available
Molecular Weight:117.1479
Molecular Formula:C8H7N
SMILES:N1C=CC2=CC=CC=C12
InChI:1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
InChIKey:SIKJAQJRHWYJAI-UHFFFAOYSA-N
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Compound 64
Drug synonym:Not Available
Molecular Weight:67.0892
Molecular Formula:C4H5N
SMILES:N1C=CC=C1
InChI:1S/C4H5N/c1-2-4-5-3-1/h1-5H
InChIKey:KAESVJOAVNADME-UHFFFAOYSA-N
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Compound 65
Drug synonym:Not Available
Molecular Weight:118.1326
Molecular Formula:C8H6O
SMILES:O1C=CC2=CC=CC=C12
InChI:1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
InChIKey:IANQTJSKSUMEQM-UHFFFAOYSA-N
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Compound 66
Drug synonym:Not Available
Molecular Weight:182.2212
Molecular Formula:C12H10N2
SMILES:C1=CC=C(C=C1)\N=N\C1=CC=CC=C1
InChI:1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H/b14-13+
InChIKey:DMLAVOWQYNRWNQ-BUHFOSPRSA-N
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Compound 67
Drug synonym:Not Available
Molecular Weight:85.128
Molecular Formula:C3H3NS
SMILES:S1C=CN=C1
InChI:Not Available
InChIKey:Not Available
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Compound 68
Drug synonym:Not Available
Molecular Weight:134.198
Molecular Formula:C8H6S
SMILES:S1C=CC2=CC=CC=C12
InChI:1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
InChIKey:FCEHBMOGCRZNNI-UHFFFAOYSA-N
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Compound 69a
Drug synonym:Not Available
Molecular Weight:267.3257
Molecular Formula:C16H17N3O
SMILES:COC[C@@H]1CC[C@@H]2N1c1ccccc1CC2(C#N)C#N
InChI:1S/C16H17N3O/c1-20-9-13-6-7-15-16(10-17,11-18)8-12-4-2-3-5-14(12)19(13)15/h2-5,13,15H,6-9H2,1H3/t13-,15-/m0/s1
InChIKey:OASFUPNFUGXVOE-ZFWWWQNUSA-N
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Compound 69b
Drug synonym:Not Available
Molecular Weight:281.3523
Molecular Formula:C17H19N3O
SMILES:COC[C@@H]1CC[C@@H]2N1c1ccccc1[C@H](C)C2(C#N)C#N
InChI:1S/C17H19N3O/c1-12-14-5-3-4-6-15(14)20-13(9-21-2)7-8-16(20)17(12,10-18)11-19/h3-6,12-13,16H,7-9H2,1-2H3/t12-,13-,16-/m0/s1
InChIKey:PMGMJABYWZUNPL-XEZPLFJOSA-N
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Compound 70
Drug synonym:Not Available
Molecular Weight:569.425
Molecular Formula:C29H34N4Zn2
SMILES:[Zn+].[Zn+].CCC1=C(C)C=N\C1=C\c1[n-]c(C)c(CC2=C(C)\C(=C/c3[n-]cc(C)c3CC)N=C2C)c1C
InChI:1S/C29H34N4.2Zn/c1-9-22-16(3)14-30-28(22)12-26-18(5)24(20(7)32-26)11-25-19(6)27(33-21(25)8)13-29-23(10-2)17(4)15-31-29;;/h12-15H,9-11H2,1-8H3;;/q-2;2*+1/b26-12+,29-13+;;
InChIKey:XLGVAPWOPWCJSJ-ZQKGCYIASA-N
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Compound 71
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 69
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 72
Drug synonym:Not Available
Molecular Weight:304.1706
Molecular Formula:C11H17IN2
SMILES:[I-].CN1CCCC1c1ccc[n+](C)c1
InChI:1S/C11H17N2.HI/c1-12-7-3-5-10(9-12)11-6-4-8-13(11)2;/h3,5,7,9,11H,4,6,8H2,1-2H3;1H/q+1;/p-1
InChIKey:DYAGPCQOMOCCFX-UHFFFAOYSA-M
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Compound 73
Drug synonym:Not Available
Molecular Weight:240.069
Molecular Formula:C9H13BF4S
SMILES:F[B-](F)(F)F.CC[S+](C)c1ccccc1
InChI:1S/C9H13S.BF4/c1-3-10(2)9-7-5-4-6-8-9;2-1(3,4)5/h4-8H,3H2,1-2H3;/q+1;-1
InChIKey:BBLYMGLIKYPOAG-UHFFFAOYSA-N
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Compound 74
Drug synonym:Not Available
Molecular Weight:568.6961
Molecular Formula:C30H48O10
SMILES:CC(C)(C)c1ccc2OCCOCCO[C@H]([C@H]3COC(C)(C)O3)[C@H](OCCOCCOc2c1)[C@H]1COC(C)(C)O1
InChI:1S/C30H48O10/c1-28(2,3)21-8-9-22-23(18-21)34-15-11-32-13-17-36-27(25-20-38-30(6,7)40-25)26(24-19-37-29(4,5)39-24)35-16-12-31-10-14-33-22/h8-9,18,24-27H,10-17,19-20H2,1-7H3/t24-,25-,26-,27-/m1/s1
InChIKey:XBYMBVDJRZHLJT-FPCALVHFSA-N
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