Select a section from the left sidebar
Podophyllotoxin
- Family: Plantae - Cupressaceae
- Kingdom: Plantae
- Class: Lignan
| Canonical Smiles | COc1cc(cc(c1OC)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O |
|---|---|
| InChI | InChI=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 |
| InChIKey | YJGVMLPVUAXIQN-XVVDYKMHSA-N |
| Formula | C22H22O8 |
| HBA | 8 |
| HBD | 1 |
| MW | 414.41 |
| Rotatable Bonds | 4 |
| TPSA | 92.68 |
| LogP | 2.41 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.41 |
| Exact Mass | 414.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Juniperus species | Cupressaceae | Plantae | 13100 |
Showing of synonyms
Podophyllotoxin
Podofilox
518-28-5
(-)-Podophyllotoxin
Podophyllotoxin 7
Podophyllinic acid lactone
Warticon
Podofilm
Podophilox
CCRIS 565
HSDB 7238
EINECS 208-250-4
NSC 24818
NSC-24818
DTXSID3045645
UNII-L36H50F353
CHEBI:50305
AI3-50456
L36H50F353
(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
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))-
DTXCID1025645
(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 (MART.)
PODOPHYLLOTOXIN [MART.]
PODOPHYLLOTOXIN (EP MONOGRAPH)
PODOPHYLLOTOXIN [EP MONOGRAPH]
(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
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
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,5aR,8aR,9R)-5,8,8a,9-tetrahydro-9-hdroxy-5-(3,4,5-trimethoxyphenyl)furo-
1-hydroxy-2-hydroxymethyl-6,7-methylenedioxy-4-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthal ene-3-carboxylic acid lactone
208-250-4
Condylox
Condyline
Wartec
Podofilox [USAN]
MFCD00075290
(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
NSC24818
CHEMBL61
(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
MLS000069495
Podofilox (USAN)
NCGC00022001-05
Podophyllum
SMR000059121
(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)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
Podocon-25
SR-05000001749
MLS002702981
Podofillina
Podophylotoxin
Mayapple isolate
Condylox (TN)
CAS-518-28-5
Prestwick_1018
Podofilox (Standard)
Podofillina [Italian]
Podophyllotoxin (BAN)
Spectrum_000199
PODOFILOX [HSDB]
Opera_ID_1397
Prestwick0_000782
Prestwick1_000782
Prestwick2_000782
Prestwick3_000782
Spectrum2_000878
Spectrum4_000592
Spectrum5_001368
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
PODOFILOX [ORANGE BOOK]
PODOPHYLLOTOXIN [WHO-DD]
UPCMLD-DP035:001
UPCMLD-DP035:002
BCBcMAP01_000165
GTPL13598
HMS500O14
KBio1_000292
KBio2_000679
KBio2_003247
KBio2_005815
NINDS_000292
16902YVY2B
GLXC-10126
HMS1570M06
HMS2093P16
HMS2097M06
HMS2235A23
HMS3259J19
HMS3714M06
Pharmakon1600-02300332
ALBB-020906
BCP24085
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.))-
Podophyllotoxin, analytical standard
EINECS 232-546-2
Tox21_110874
Tox21_202922
B18-5C
BBL033695
BDBM50035218
CCG-39894
HY-15552R
MSK000573
NSC759591
STK801918
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
(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
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)-
HY-15552
NCI60_001981
RD4-6269
1ST000573
NS00094687
P1771
EN300-52746
D05529
A828801
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
(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-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
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
Pubchem:
10607
Cas:
518-28-5
Gnps:
CCMSLIB00000077107
Zinc:
ZINC000003861806
Kegg Ligand:
C10874
Chebi:
50305
Nmrshiftdb2:
60022424
Metabolights:
MTBLC50305
Chembl:
CHEMBL61
Comptox:
DTXSID3045645
Drugbank:
DB01179
Pdb Ligand:
POD
Bindingdb:
50035218
CPRiL:
6447
SMILES: O1COc(c12)cc3c(c2)C(C4C(C3)COC4=O)c5ccccc5
Level: 1
Mol. Weight: 414.41 g/mol
SMILES: O1COc(c12)cc3c(c2)CC4C(C3)COC4=O
Level: 0
Mol. Weight: 414.41 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 414.41 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.92
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.780
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.940
- Plasma Protein Binding
- 71.43
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.590
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.420
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.450
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.310
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -67.900
- Rat (Acute)
- 2.420
- Rat (Chronic Oral)
- 2.120
- Fathead Minnow
- 4.850
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 486.690
- Hydration Free Energy
- -3.350
- Log(D) at pH=7.4
- 1.940
- Log(P)
- 1.94
- Log S
- -3.36
- Log(Vapor Pressure)
- -8.98
- Melting Point
- 200.51
- pKa Acid
- 8.46
- pKa Basic
- 1.56
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.9033 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.9033 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8759 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8759 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8681 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8681 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8291 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8291 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8185 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8185 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8085 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8085 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7614 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7614 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 4 | 0.7508 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 4 | 0.7508 |
| Rifampin ADP-ribosyl transferase | A0QRS5 | A0QRS5_MYCS2 | Mycolicibacterium smegmatis155) | 3 | 0.7309 |
| Rifampin ADP-ribosyl transferase | A0QRS5 | A0QRS5_MYCS2 | Mycolicibacterium smegmatis155) | 3 | 0.7309 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7272 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7272 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7267 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7267 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7251 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7251 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7249 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7249 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7141 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7141 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7124 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7124 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7105 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7105 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 4 | 0.7090 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 4 | 0.7090 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7033 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7033 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7021 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7021 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7004 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7004 |