Podofilox

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Podofilox are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Podofilox?

The molecule Podofilox presents a molecular formula of C22H22O8 and its IUPAC name is (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.

Podofilox (Condylox) is a topical gel used to treat genital warts. It works by causing the warts to shrink and eventually disappear. Podofilox exists over-the-counter (OTC) and by prescription..

Podofilox belongs to a class of drugs known as anti-mitotics. It works by stopping the growth of the wart-causing virus. The gel is applied directly to the warts. It is usually applied once or twice a day for three days, followed by four days of no treatment. This cycle is repeated for up to four weeks..

Side effects of podofilox include skin irritation, burning, and itching. These side effects are usually mild and go away on their own. More serious side effects are rare but can include allergic reactions and skin ulcers..

Podofilox is an effective treatment for genital warts. It is safe for most people to use, but there are a few potential side effects to be aware of. If you experience any serious side effects, stop using the gel and talk to your doctor..

3D structure

Cartesian coordinates

Geometry of Podofilox in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Podofilox YJGVMLPVUAXIQN-XVVDYKMHSA-N chemical compound 2D structure molecule svg
Podofilox

 

Molecule descriptors

 
IUPAC name(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
InChI codeInChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
InChI KeyYJGVMLPVUAXIQN-XVVDYKMHSA-N
SMILESCOc1cc([C@@H]2c3cc4c(cc3[C@H](O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-Podophyllotoxin
  • (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?,?.0??,??]hexadeca-1(9),2,7-trien-12-one
  • (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
  • (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)-5,8,8a,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)-5,8,8a,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-[2]benzofuro[5,6-f][1,3]benzodioxol-8-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)-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)-5-oxidanyl-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-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
  • (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
  • (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
  • 1,3,3a,4,9,9a-Hexahydro-9-hydroxy-6,7-(methylenedioxy)-4-(3',4',5'-trimethoxyphenyl)benz(f)isobenzofuran-3-one
  • 11016-28-7
  • 16902YVY2B
  • 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.)]
  • 518-28-5
  • 518P285
  • 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
  • A828801
  • AC-1656
  • AI3-50456
  • AMY2648
  • B18-5C
  • BBL033695
  • BCBcMAP01_000165
  • BCP24085
  • BDBM50035218
  • BIDD:GT0123
  • BPBio1_000974
  • BSPBio_000884
  • BSPBio_002352
  • CCG-39894
  • CCRIS 4391
  • CCRIS 565
  • CS-1185
  • Condyline
  • Condylox
  • D05529
  • DB01179
  • DSSTox_CID_25645
  • DSSTox_GSID_45645
  • DSSTox_RID_81023
  • DivK1c_000292
  • EN300-52746
  • 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.))-
  • 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))-
  • 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.)]-
  • HMS1570M06
  • HMS2093P16
  • HMS2097M06
  • HMS2235A23
  • HMS3259J19
  • HMS3714M06
  • HMS500O14
  • HSDB 7238
  • HY-15552
  • IDI1_000292
  • KBio1_000292
  • KBio2_000679
  • KBio2_003247
  • KBio2_005815
  • KBioGR_001084
  • KBioSS_000679
  • KS-1281
  • L36H50F353
  • MFCD00075290
  • MLS000069495
  • MLS001148204
  • MLS002172467
  • MLS002702981
  • MLS006010754
  • MLS006011412
  • Mayapple isolate
  • NC00675
  • NCGC00022001-03
  • NCGC00022001-05
  • NCGC00022001-07
  • NCGC00022001-08
  • NCGC00022001-09
  • NCGC00022001-10
  • NCGC00022001-11
  • NCGC00022001-13
  • NCGC00022001-14
  • NCGC00260468-01
  • NCI60_001981
  • ND-1185
  • NINDS_000292
  • NSC 24818
  • NSC-24818
  • NSC-759591
  • NSC24818
  • NSC759591
  • Naphtho[2,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl-, .gamma.-lactone
  • Opera_ID_1397
  • P-6980
  • P1771
  • Pharmakon1600-02300332
  • Podocon-25
  • Podofilm
  • Podofilox
  • Podofilox (USAN)
  • Podofillina
  • Podophilox
  • Podophylotoxin
  • Podophyllinic acid lactone
  • Podophyllotoxin (BAN)
  • Podophyllotoxin 7
  • Podophyllotoxin,(S)
  • Podophyllum
  • Prestwick0_000782
  • Prestwick1_000782
  • Prestwick2_000782
  • Prestwick3_000782
  • Prestwick_1018
  • Q421193
  • RD4-6269
  • SDCCGMLS-0066888.P001
  • SMP1_000243
  • SMR000059121
  • SR-01000003030
  • SR-01000003030-3
  • SR-05000001749
  • SR-05000001749-1
  • SR-05000001749-2
  • STK801918
  • Wartec
  • Warticon
  • Z1258578359
  • 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)-
  • podophyllotoxin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3861806
  • CAS-518-28-5
  • UNII-L36H50F353
  • UNII-16902YVY2B
  • AKOS000265559
  • ALBB-020906
  • BRD-K47869605-001-05-6
  • BRD-K47869605-001-18-9
  • DTXSID3045645
  • CHEMBL61
  • CHEBI:50305
  • Tox21_110874
  • Tox21_202922
  • Tox21_110874_1
  • EINECS 208-250-4
  • EINECS 232-546-2
  • SPBio_000955
  • SPBio_002823
  • UPCMLD-DP035
  • UPCMLD-DP035:001
  • UPCMLD-DP035:002
  • SCHEMBL42243
  • Spectrum_000199
  • Spectrum2_000878
  • Spectrum4_000592
  • Spectrum5_001368

Physico-Chemical properties

IUPAC name(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
Molecular formulaC22H22O8
Molecular weight414.405
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity103.85
LogP2.4
Topological polar surface area92.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.