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Picropodophyllotoxin
- 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
Picropodophyllotoxin
Picropodophyllin
477-47-4
AXL1717
Picropodophyllin (PPP)
Cyclolignan PPP
Picro-podophyllin
AXL-1717
NSC 36407
NSC36407
UNII-0F35AOI227
BRN 0099161
CHEBI:75251
0F35AOI227
AXL 1717
(5R,5aS,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
PICROPODOPHYLLIN [WHO-DD]
DTXSID80197245
PODOPHYLLOTOXIN IMPURITY A [EP IMPURITY]
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-alpha,8a-alpha,9-alpha))-
(5R,5AS,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,5aS,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
PODOPHYLLOTOXIN IMPURITY A (EP IMPURITY)
(5R,5aS,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
Picropodophyllin (8CI)
DTXCID90119736
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-alpha,8a-alpha,9-alpha))-
5-19-10-00665 (beilstein handbook reference)
(-)PPP
IGF-1R Inhibitor, PPP
NSC-36407
Podophyllotoxin picropodophyllin
(5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
17434-18-3
AXL1717 (Picropodophyllotoxin)
PPP
MFCD01742647
Spectrum_001636
Spectrum2_000520
Spectrum3_001671
Spectrum4_001836
Spectrum5_000631
BSPBio_003481
KBioGR_002538
KBioSS_002116
1352873-82-5
SCHEMBL159598
SPECTRUM1504410
SPBio_000479
CHEMBL283120
GTPL7873
KBio2_002116
KBio2_004684
KBio2_007252
KBio3_002701
YJGVMLPVUAXIQN-HAEOHBJNSA-N
HMS1923O05
BCP18482
EX-A4921
CCG-39920
NSC799342
S7668
AKOS015965529
CS-1184
DB12802
FP63882
NSC-799342
SDCCGMLS-0066757.P001
NCGC00161923-01
NCGC00161923-02
NCGC00161923-04
NCGC00161923-29
AC-20289
AC-36894
BS-16874
DA-56856
HY-15494
NS00009071
PODOPHYLLOTOXIN PICROPODOPHYLLIN [MI]
Picropodophyllotoxin, >=96% (HPLC), powder
EN300-24434020
BRD-K81829253-001-02-9
BRD-K81829253-001-03-7
Q27088385
WLN: T E5 C665 FVO NO PO OHTT&&J DR CO1 DO1 EO1& JQ
(10R,11S,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0(3),?.0(1)(1),(1)?]hexadeca-1(9),2,7-trien-12-one
(10R,11S,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,11S,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,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
118627-04-6
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-(.alpha.-5a.alpha.,8a.alpha.,9.alpha.)]
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.alpha.,8a.alpha.,9.alpha.)]-
Pubchem:
72435
Cas:
477-47-4
Gnps:
CCMSLIB00004689995
Zinc:
ZINC000004098919
Chebi:
75251
Nmrshiftdb2:
70005656
Metabolights:
MTBLC75251
Chembl:
CHEMBL283120
Comptox:
DTXSID80197245
Drugbank:
DB12802
CPRiL:
57203
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
- -2.32
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 |