Picropodophyllotoxin - Compound Card

Picropodophyllotoxin

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Picropodophyllotoxin

Structure
Zoomed Structure
  • 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-HAEOHBJNSA-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

  • 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]
CPRiL: 57203
Structure

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

Level: 1

Mol. Weight: 414.41 g/mol

Structure

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

Level: 0

Mol. Weight: 414.41 g/mol

Structure

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
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.940
Plasma Protein Binding
72.2
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
12.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.450
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
-67.850
Rat (Acute)
2.410
Rat (Chronic Oral)
2.120
Fathead Minnow
4.870
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
486.580
Hydration Free Energy
-3.330
Log(D) at pH=7.4
1.900
Log(P)
1.84
Log S
-3.36
Log(Vapor Pressure)
-9.01
Melting Point
202.5
pKa Acid
8.46
pKa Basic
1.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9460
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9460
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9324
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9324
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9100
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9100
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8751
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8751
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8724
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8724
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8461
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8461
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8204
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8204
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8171
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8171
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8037
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8037
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.8022
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.8022
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7840
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7840
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7834
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7834
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7791
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7791
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7701
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7701
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7609
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7609
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7541
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7541
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7514
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7514
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7497
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7497
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7481
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7481
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7423
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7423
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7408
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7408
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7406
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7406
L-lactate dehydrogenase Q5SJA1 LDH_THET8 Thermus thermophilus 3 0.7391
L-lactate dehydrogenase Q5SJA1 LDH_THET8 Thermus thermophilus 3 0.7391
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7351
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7351
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7340
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7340
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7319
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7319
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7287
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7287
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7234
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7234
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7230
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7230
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7226
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7226
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7217
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7217
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7202
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7202
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7149
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7149
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7116
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7116
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7111
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7111
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7110
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7110
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7109
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7109
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7055
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7055
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7054
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7054
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7044
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7044
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7025
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7025
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7014
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7014
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7007
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7007
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7002
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7002

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