Compound: podophyllotoxin
SMILES: O=C1OC[C@H]2[C@H]1[C@@H](c3c(cc4OCOc4c3)[C@@H]2O)c5cc(OC)c(OC)c(c5)OC
InChIKey: YJGVMLPVUAXIQN-XVVDYKMHSA-N
Synonyms: podophyllotoxin, Podofilox, 518-28-5, Condylox, (-)-Podophyllotoxin, Podophyllinic acid lactone, Podophyllotoxin 7, Wartec, Warticon, Podofilm, NSC-24818, (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one, DTXSID3045645, L36H50F353, DTXCID1025645, CHEBI:50305, (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one, 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-(5alpha,5abeta,8aalpha,9alpha))-, (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one, (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo(7.7.0.0^(3,7).0^(11,15))hexadeca-1(9),2,7-trien-12-one, (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo(7.7.0.03,7.011,15)hexadeca-1,3(7),8-trien-12-one, (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-(2)benzofuro(5,6-f)(1,3)benzodioxol-8-one, 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, RefChem:56693, 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, 208-250-4, Condyline, Podofilox [USAN], MFCD00075290, NSC24818, CHEMBL61, MLS000069495, (5R,5aR,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, (5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one, Podofilox (USAN), (5R,5aR,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, (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one, (5R,5aR,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, NCGC00022001-05, SMR000059121, NSC 24818, 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,5aR,8aR,9R)-, Podophilox, (5R,9R,5aR,8aR)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,9,5a,8a-pentahydro-2H -isobenzofurano[5',6'-2,1]benzo[4,5-d]1,3-dioxolan-6-one, CCRIS 565, Podocon-25, HSDB 7238, SR-05000001749, MLS002702981, EINECS 208-250-4, Podofillina, Podophylotoxin, podophyllotoxine, AI3-50456, Condyline;, Mayapple isolate, Condylox;, UNII-L36H50F353, Condylox (TN), CAS-518-28-5, Podophyllotoxin CRS, Prestwick_1018, Podofilox (Standard), Podofillina [Italian], Podophyllotoxin (BAN), Spectrum_000199, Etoposide EP Impurity M, PODOFILOX [HSDB], Opera_ID_1397, Prestwick0_000782, Prestwick1_000782, Prestwick2_000782, Prestwick3_000782, Spectrum2_000878, Spectrum4_000592, Spectrum5_001368, GlyTouCan:G88801WQ, PODOFILOX [VANDF], UPCMLD-DP035, PODOPHYLLOTOXIN [MI], SCHEMBL42243, BSPBio_000884, BSPBio_002352, KBioGR_001084, KBioSS_000679, MLS001148204, MLS002172467, MLS006010754, MLS006011412, BIDD:GT0123, DivK1c_000292, UNII-16902YVY2B, SPBio_000955, SPBio_002823, BPBio1_000974, CCRIS 4391, orb1309699, orb3139929, PODOFILOX [ORANGE BOOK], PODOPHYLLOTOXIN [MART.], PODOPHYLLOTOXIN [WHO-DD], SCHEMBL29351029, UPCMLD-DP035:001, UPCMLD-DP035:002, BCBcMAP01_000165, GTPL13598, HMS500O14, KBio1_000292, KBio2_000679, KBio2_003247, KBio2_005815, NINDS_000292, GLXC-10126, HMS1570M06, HMS2093P16, HMS2097M06, HMS2235A23, HMS3259J19, HMS3714M06, Pharmakon1600-02300332, ALBB-020906, 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-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.ALPHA.))-, G88801WQ, Podophyllotoxin, analytical standard, EINECS 232-546-2, Tox21_110874, Tox21_202922, B18-5C, BBL033695, BDBM50035218, CCG-39894, EBC-12795, HY-15552R, MSK000573, NSC759591, STK801918, PODOPHYLLOTOXIN [EP MONOGRAPH], AKOS000265559, Tox21_110874_1, AC-1656, CS-1185, DB01179, FP05386, KS-1281, NC00675, ND-1185, NSC-759591, SDCCGMLS-0066888.P001, IDI1_000292, SMP1_000243, NCGC00022001-03, NCGC00022001-07, NCGC00022001-08, NCGC00022001-09, NCGC00022001-10, NCGC00022001-11, NCGC00022001-13, NCGC00022001-14, NCGC00260468-01, 1,3,3a,4,9,9a-Hexahydro-9-hydroxy-6,7-(methylenedioxy)-4-(3',4',5'-trimethoxyphenyl)benz(f)isobenzofuran-3-one, HY-15552, NCI60_001981, RD4-6269, ST066914, Etoposide EP Impurity M (Podophyllotoxin), NS00094687, P1771, EN300-52746, D05529, AO-228/21245006, Q421193, SR-01000003030, SR-01000003030-3, SR-05000001749-1, SR-05000001749-2, BRD-K47869605-001-05-6, BRD-K47869605-001-18-9, BRD-K47869605-001-32-0, Z759291658, (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0?,?.0??,??]hexadeca-1(9),2,7-trien-12-one, (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one, (5R,5aR,8aR,9R)-9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one, (5R,5aR,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 (podophyllotoxin), 11016-28-7, 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, [5R-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)], Furo[3',4':6,7]naphtha[2,3-d]-1,3-dioxol-6(5?H)-one, 5,8,8?,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl), Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]-, Naphtho[2,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl-, .gamma.-lactone
Theoretical properties:
molecular_formula: C22H22O8
molecular_weight: 414.4 g/mol
exact_mass: 414.13146766 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 4
heavy_atom_count: 30
topological_polar_surface_area: 92.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Solvated crystals
color: Solvated crystals
vapor_pressure: 8.3X10-15 mm Hg at 25 °C /Estimated/
Descriptions:
pubchem: Podophyllotoxin is an organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing a 3,4,5-trimethoxyphenyl substituent. It is found in the roots and rhizomes of Podophyllum species and is used for the topical treatment of genital warts. It has a role as an antineoplastic agent, a keratolytic drug, a tubulin modulator, a microtubule-destabilising agent, an antimitotic and a plant metabolite. It is a lignan, an organic heterotetracyclic compound and a furonaphthodioxole.
chebi: An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing a 3,4,5-trimethoxyphenyl substituent. It is found in the roots and rhizomes of <em>Podophyllum</em> species and is used for the topical treatment of genital warts.
chembl: PODOFILOX is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Podophyllotoxin (PPT) is the active ingredient in Podofilox, a medical cream used to treat genital warts and molluscum contagiosum. It is not recommended for HPV infections without external warts. It can be applied either by a healthcare provider or the patient themselves.
Podophyllotoxin is a non-alkaloid lignan extracted from the roots and rhizomes of plants of the genus Podophyllum. A less refined form known as podophyllum resin is also available, but has greater side effects.
Podophyllotoxin was first isolated in pure form in 1880 by Valerian Podwyssotzki (1818 – 28 January 1892), a Polish-Russian privatdozent at the University of Dorpat (now Tartu, Estonia) and assistant at the Pharmacological Institute there.
PPT is on the World Health Organization's List of Essential Medicines.