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Lignans and related compounds

Lignans and neolignans are naturally occurring polyphenol dimers commonly found in plants; polyphenols are compounds containing several phenol rings (phenols are aromatic rings with a hydroxyl group). Includes similar polyphenolic compounds.

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1

Alpha-Etoposide, TRC

CAS: 100007-53-2 Molecular Formula: C29H32O13 Molecular Weight (g/mol): 588.56 Synonym: (5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-α-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,Pyrano[3,2-d]-1,3-dioxin Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one Deriv. SMILES: COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26

CAS 100007-53-2
Molecular Weight (g/mol) 588.56
SMILES COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26
Synonym (5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-α-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,Pyrano[3,2-d]-1,3-dioxin Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one Deriv.
Molecular Formula C29H32O13
2

Picropodophyllotoxin, TRC

CAS: 477-47-4 Molecular Formula: C22 H22 O8 Molecular Weight (g/mol): 414.41 Synonym: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aS,8aR,9R)-,Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5α,5aα,8aα,9α)]-,Picropodophyllin (6CI,7CI,8CI),(5R,5aS,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,AXL 1717,NSC 36407,Picropodophyllotoxin,(5R,5aS,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one IUPAC Name: (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one SMILES: COc1cc(cc(OC)c1OC)[C@H]2[C@H]3[C@H](COC3=O)[C@@H](O)c4cc5OCOc5cc24

CAS 477-47-4
Molecular Weight (g/mol) 414.41
SMILES COc1cc(cc(OC)c1OC)[C@H]2[C@H]3[C@H](COC3=O)[C@@H](O)c4cc5OCOc5cc24
Synonym Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aS,8aR,9R)-,Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5α,5aα,8aα,9α)]-,Picropodophyllin (6CI,7CI,8CI),(5R,5aS,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,AXL 1717,NSC 36407,Picropodophyllotoxin,(5R,5aS,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
IUPAC Name (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Molecular Formula C22 H22 O8
4

cis-Etoposide, TRC

CAS: 100007-56-5 Molecular Formula: C29 H32 O13 Molecular Weight (g/mol): 588.56 Synonym: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aS,8aR,9S)-,Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-[5α,5aα,8aα,9β(R*)]]-,(5R,5aS,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,Pyrano[3,2-d]-1,3-dioxin, furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one deriv.,Picro ethylidene lignan P,Picroetoposide,Pptoxin IV,cis-Etoposide,(5R,5aS,8aR,9S)-9-[[4,6-O-[(1R)-ethane-1,1-diyl]-β-D-glucopyranosyl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro[2]benzofuro[5,6-f][1,3]benzodioxol-6(5aH)-one IUPAC Name: (5S,5aR,8aS,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one SMILES: COc1cc(cc(OC)c1O)[C@H]2[C@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26

CAS 100007-56-5
Molecular Weight (g/mol) 588.56
SMILES COc1cc(cc(OC)c1O)[C@H]2[C@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26
Synonym Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aS,8aR,9S)-,Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-[5α,5aα,8aα,9β(R*)]]-,(5R,5aS,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,Pyrano[3,2-d]-1,3-dioxin, furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one deriv.,Picro ethylidene lignan P,Picroetoposide,Pptoxin IV,cis-Etoposide,(5R,5aS,8aR,9S)-9-[[4,6-O-[(1R)-ethane-1,1-diyl]-β-D-glucopyranosyl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro[2]benzofuro[5,6-f][1,3]benzodioxol-6(5aH)-one
IUPAC Name (5S,5aR,8aS,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Molecular Formula C29 H32 O13
5

Lignan P, TRC

CAS: 23363-35-1 Molecular Formula: C27 H30 O13 Molecular Weight (g/mol): 562.52 Synonym: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-(β-D-glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-,Epipodophyllotoxin, 4'-demethyl-, 9-β-D-glucopyranoside (8CI),Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-(β-D-glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-(5α,5aβ,8aα,9β)]-,(5R,5aR,8aR,9S)-9-(β-D-Glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,Glucopyranoside, 4'-demethylepipodophyllotoxin, β-D- (8CI),4-Demethylepipodophyllotoxin 7'-O-β-D-glucopyranoside,4'-Demethylepipodophyllotoxin glucoside,4'-Demethylepipodophyllotoxin β-D-glucopyranoside,Lignan P,Pptoxin II,4'-Demethylepipodophyllotoxin 9-(β-D-glucopyranoside),(5R,5aR,8aR,9S)-9-(β-D-Glucopyranosyloxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro[2]benzofuro-[5,6-f][1,3]benzodioxol-6(5aH)-one IUPAC Name: (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one SMILES: COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c5cc6OCOc6cc25

CAS 23363-35-1
Molecular Weight (g/mol) 562.52
SMILES COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c5cc6OCOc6cc25
Synonym Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-(β-D-glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-,Epipodophyllotoxin, 4'-demethyl-, 9-β-D-glucopyranoside (8CI),Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-(β-D-glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-(5α,5aβ,8aα,9β)]-,(5R,5aR,8aR,9S)-9-(β-D-Glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,Glucopyranoside, 4'-demethylepipodophyllotoxin, β-D- (8CI),4-Demethylepipodophyllotoxin 7'-O-β-D-glucopyranoside,4'-Demethylepipodophyllotoxin glucoside,4'-Demethylepipodophyllotoxin β-D-glucopyranoside,Lignan P,Pptoxin II,4'-Demethylepipodophyllotoxin 9-(β-D-glucopyranoside),(5R,5aR,8aR,9S)-9-(β-D-Glucopyranosyloxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro[2]benzofuro-[5,6-f][1,3]benzodioxol-6(5aH)-one
IUPAC Name (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Molecular Formula C27 H30 O13
6

Etoposide, TRC

CAS: 33419-42-0 Molecular Formula: C29 H32 O13 Molecular Weight (g/mol): 588.56 Synonym: Etoposide,(5R,5aR,8aR,9S)-9-[[4,6-O-[(R)-Ethylidene]-β-d-glucopyranosyl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydroisobenzofuro[5,6-f][1,3]benzodioxol-6(5aH)-one,Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-,Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-β-D-glucopyranoside (8CI),Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-[5α,5aβ,8aα,9β(R*)]]-,(5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,Pyrano[3,2-d]-1,3-dioxin, furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one deriv.,(-)-Etoposide,4'-Demethyl-1-O-[4,6-O-(ethylidene)-β-D-glucopyranosyl]epipodophyllotoxin,4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside),4'-Demethylepipodophyllotoxin ethylidene-β-D-glucoside,Beposid,Bioposide,Celltop,EPE,Epipodophyllotoxin VP 16213,Eposed,Eposin,Ethopul,Eto-Gry,Etosid,Fytop,Fytosid,Lastet,NSC 141540,Nzytop,Sintopozid,Topok,Toposar,VP 16,VP 16 (pharmaceutical),VP 16-123,VP 16-213,VePesid,Vepesid J,Zuyeyidal,trans-Etoposide IUPAC Name: (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one SMILES: COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26

CAS 33419-42-0
Molecular Weight (g/mol) 588.56
SMILES COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26
Synonym Etoposide,(5R,5aR,8aR,9S)-9-[[4,6-O-[(R)-Ethylidene]-β-d-glucopyranosyl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydroisobenzofuro[5,6-f][1,3]benzodioxol-6(5aH)-one,Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-,Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-β-D-glucopyranoside (8CI),Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-[5α,5aβ,8aα,9β(R*)]]-,(5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,Pyrano[3,2-d]-1,3-dioxin, furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one deriv.,(-)-Etoposide,4'-Demethyl-1-O-[4,6-O-(ethylidene)-β-D-glucopyranosyl]epipodophyllotoxin,4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside),4'-Demethylepipodophyllotoxin ethylidene-β-D-glucoside,Beposid,Bioposide,Celltop,EPE,Epipodophyllotoxin VP 16213,Eposed,Eposin,Ethopul,Eto-Gry,Etosid,Fytop,Fytosid,Lastet,NSC 141540,Nzytop,Sintopozid,Topok,Toposar,VP 16,VP 16 (pharmaceutical),VP 16-123,VP 16-213,VePesid,Vepesid J,Zuyeyidal,trans-Etoposide
IUPAC Name (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Molecular Formula C29 H32 O13