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Deoxypodophyllotoxin
- Family: Plantae - Cupressaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpenoid
| Canonical Smiles | COc1cc(cc(c1OC)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2Cc2c1cc1OCOc1c2 |
|---|---|
| InChI | InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3/t13-,19+,20-/m0/s1 |
| InChIKey | ZGLXUQQMLLIKAN-SVIJTADQSA-N |
| Formula | C22H22O7 |
| HBA | 7 |
| HBD | 0 |
| MW | 398.41 |
| Rotatable Bonds | 4 |
| TPSA | 72.45 |
| LogP | 2.92 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.41 |
| Exact Mass | 398.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tetraclinis articulata | Cupressaceae | Plantae | 13717 |
Showing of synonyms
Deoxypodophyllotoxin
19186-35-7
Anthricin
4-Deoxypodophyllotoxin
Desoxypodophyllotoxin
Silicicolin
(-)-Anthricin
(-)-Deoxypodophyllotoxin
(-)-Desoxypodophyllotoxin
Hernandin
Hernandion
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)-
NSC403148
CHEBI:4429
Isodeoxypodophyllotoxin
NSC-403148
AS 2-3
100348-38-7
45NR8XYU1L
MLS002702900
Anthriscin
(5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
(5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-6-one
Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)-
CHEMBL63970
SCHEMBL987840
Podophyllotoxin, 7CI, 8CI)
Deoxypodophyllotoxin (Anthricin)
DTXSID701019944
EX-A2905
HY-N2500
AKOS032948828
AC-34638
DA-52443
FD157413
MS-26733
NCI60_003794
CS-0022771
NS00094526
F82121
Q27106380
(10R,11R,15R)-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7,011,15]hexadeca-1(9),2,7-trien-12-one
(5R,5AR,8AR)-5,8,8A,9-TETRAHYDRO-5-(3,4,5-TRIMETHOXYPHENYL)FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE
(5R,5aR,8aR)-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)-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)-5-(3,4,5-Trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5a)-one
5,8,8a,9,-Tetrahydro-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-5-(3,4,5-TRIMETHOXYPHENYL)-, (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.))- PODOPHYLLOTOXIN, DEOXY-
Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-,(5R,5aR,8aR)-
Pubchem:
345501
Cas:
19186-35-7
Zinc:
ZINC000001575139
Kegg Ligand:
C10556
Chebi:
4429
Nmrshiftdb2:
60022423
Metabolights:
MTBLC4429
Chembl:
CHEMBL63970
CPRiL:
61172
SMILES: O1COc(c12)cc3c(c2)C(C4C(C3)COC4=O)c5ccccc5
Level: 1
Mol. Weight: 398.41 g/mol
SMILES: O1COc(c12)cc3c(c2)CC4C(C3)COC4=O
Level: 0
Mol. Weight: 398.41 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 398.41 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.09
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.780
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.37
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.130
- Plasma Protein Binding
- 73.41
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- 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
- 12.420
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.660
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.520
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.800
- Micronucleos
- Safe
- 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
- -42.690
- Rat (Acute)
- 2.470
- Rat (Chronic Oral)
- 1.890
- Fathead Minnow
- 5.060
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 487.140
- Hydration Free Energy
- -4.300
- Log(D) at pH=7.4
- 2.240
- Log(P)
- 2.65
- Log S
- -4.12
- Log(Vapor Pressure)
- -8.11
- Melting Point
- 179.19
- pKa Acid
- 9.13
- pKa Basic
- 2.72
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Bromodomain testis-specific protein | Q58F21 | BRDT_HUMAN | Homo sapiens | 3 | 0.9312 |
| Bromodomain testis-specific protein | Q58F21 | BRDT_HUMAN | Homo sapiens | 3 | 0.9312 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9301 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9301 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9295 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9295 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9192 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9192 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9184 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9184 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.9115 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.9115 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.9030 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.9030 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8902 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8902 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8781 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8781 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8735 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8735 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.8394 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.8394 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.8258 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.8258 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8247 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8247 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8166 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8166 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8049 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8049 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.7992 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.7992 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7967 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7967 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7963 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7963 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7910 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7910 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7859 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7859 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7764 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7764 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7714 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7714 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7662 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7662 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7628 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7628 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7580 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7580 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7565 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7565 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7458 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7458 |
| Rifampin ADP-ribosyl transferase | A0QRS5 | A0QRS5_MYCS2 | Mycolicibacterium smegmatis155) | 3 | 0.7310 |
| Rifampin ADP-ribosyl transferase | A0QRS5 | A0QRS5_MYCS2 | Mycolicibacterium smegmatis155) | 3 | 0.7310 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7299 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7299 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7292 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7292 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7272 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7272 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7256 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7256 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 3 | 0.7254 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 3 | 0.7254 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7253 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7253 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.7182 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.7182 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7181 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7181 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7180 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7180 |
| Pteridine reductase | O76290 | O76290_TRYBB | Trypanosoma brucei brucei | 2 | 0.7166 |
| Pteridine reductase | O76290 | O76290_TRYBB | Trypanosoma brucei brucei | 2 | 0.7166 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 4 | 0.7140 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 4 | 0.7140 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7109 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7109 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7107 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7107 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7069 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7069 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7045 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7045 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7039 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7039 |
| Activin receptor type-1 | Q04771 | ACVR1_HUMAN | Homo sapiens | 3 | 0.7022 |
| Activin receptor type-1 | Q04771 | ACVR1_HUMAN | Homo sapiens | 3 | 0.7022 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7019 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7019 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7001 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7001 |