Deoxypodophyllotoxin - Compound Card

Deoxypodophyllotoxin

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Deoxypodophyllotoxin

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles COc1cc(cc(c1OC)OC)[C@H]1C2C(=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-XIXJEIPKSA-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 Juniperus species Cupressaceae Plantae 13100

Showing of synonyms

  • Barrero AF, Quılez del Moral JF, et al. (2004). Oxygenated diterpenes and other constituents from Moroccan Juniperus phoenicea and Juniperus thurifera var. africana. Phytochemistry,2004,65,2507-2515. [View] [PubMed]
Pubchem: 71045228
Nmrshiftdb2: 80005127
CPRiL: 61172
Structure

SMILES: O1COc(c12)cc3c(c2)C(C4C(C3)COC4=O)c5ccccc5

Level: 1

Mol. Weight: 398.41 g/mol

Structure

SMILES: O1COc(c12)cc3c(c2)CC4C(C3)COC4=O

Level: 0

Mol. Weight: 398.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 398.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.1
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
70.57
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
12.380
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.770
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
6.810
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
-42.850
Rat (Acute)
2.460
Rat (Chronic Oral)
1.880
Fathead Minnow
5.240
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
484.530
Hydration Free Energy
-4.290
Log(D) at pH=7.4
2.240
Log(P)
2.71
Log S
-4.1
Log(Vapor Pressure)
-8.06
Melting Point
175.82
pKa Acid
9.16
pKa Basic
2.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9437
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9437
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9310
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9310
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9223
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9223
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8960
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8960
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8917
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8917
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8907
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8907
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8863
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8863
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8837
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8837
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8754
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8754
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8686
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8686
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8605
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8605
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8586
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8586
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8562
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8562
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8544
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8544
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8357
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8357
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8334
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8334
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8289
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8289
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8270
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8270
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8146
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8146
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8104
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8104
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8085
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8085
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8005
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8005
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7917
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7917
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7767
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7767
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7738
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7738
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7683
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7683
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7650
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7650
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7617
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7617
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7596
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7596
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7554
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7554
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7554
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7554
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7528
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7528
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7510
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7510
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7494
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7494
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7424
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7424
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7395
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7395
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7379
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7379
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7351
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7351
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7347
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7347
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7343
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7343
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7315
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7315
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7300
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7300
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7236
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7236
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7231
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7231
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7226
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7226
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7204
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7204
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7203
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7203
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7202
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7202
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7193
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7193
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 2 0.7150
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 2 0.7150
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7146
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7146
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7141
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7141
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7138
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7138
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7110
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7110
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7107
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7107
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7091
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7091
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7082
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7082
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7074
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7074
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7033
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7033
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7004
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7004

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