Diphyllin - Compound Card

Diphyllin

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Diphyllin

Structure
Zoomed Structure
  • Family: Animalia - Apidae
  • Kingdom: Animalia, Plantae
  • Class: Lignan
    • Subclass: Naphthalide Lignan
Canonical Smiles COc1cc2c(c3ccc4c(c3)OCO4)c3C(=O)OCc3c(c2cc1OC)O
InChI InChI=1S/C21H16O7/c1-24-15-6-11-12(7-16(15)25-2)20(22)13-8-26-21(23)19(13)18(11)10-3-4-14-17(5-10)28-9-27-14/h3-7,22H,8-9H2,1-2H3
InChIKey VMEJANRODATDOF-UHFFFAOYSA-N
Formula C21H16O7
HBA 7
HBD 1
MW 380.35
Rotatable Bonds 3
TPSA 83.45
LogP 3.63
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 380.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Apis species Apidae Animalia 7459
2 Haplophyllum tuberculatum Rutaceae Plantae 452784

Showing of synonyms

  • Sheriha GM, Abou Amer KM (1984). Lignans of Haplophyllum tuberculatum. Phytochemistry,1984,23(1),151-153. [View]
  • Petrova A, Popova M, et al. (2010). New biologically active compounds from Kenyan propolis.. Fitoterapia,2010,81(6),509-514. [View] [PubMed]
Pubchem: 100492
Kegg Ligand: C10559
Chebi: 4645
Nmrshiftdb2: 60019988
Bindingdb: 64979
CPRiL: 76452
Structure

SMILES: O=C1OCc(c12)cc3c(cccc3)c2-c(c4)ccc(c45)OCO5

Level: 1

Mol. Weight: 380.35 g/mol

Structure

SMILES: O=C1OCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 380.35 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 380.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.270
Plasma Protein Binding
76.05
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.710
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.860
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.850
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-23.560
Rat (Acute)
2.620
Rat (Chronic Oral)
1.760
Fathead Minnow
5.510
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
492.320
Hydration Free Energy
-4.880
Log(D) at pH=7.4
2.920
Log(P)
3.13
Log S
-4.33
Log(Vapor Pressure)
-8.98
Melting Point
215.68
pKa Acid
8.13
pKa Basic
1.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9119
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9119
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8991
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8991
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8965
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8965
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8824
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8824
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8665
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8665
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8629
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8629
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8586
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8586
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8576
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8576
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8554
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8554
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8537
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8537
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8432
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8432
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8417
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8417
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8404
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8404
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8272
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8272
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8234
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8234
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8224
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8224
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8141
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8141
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.8125
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.8125
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8014
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8014
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8004
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8004
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7979
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7979
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7938
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7938
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7937
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7937
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7868
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7868
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7844
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7844
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7828
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7828
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7806
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7806
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7794
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7794
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7735
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7735
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7735
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7735
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7726
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7726
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7720
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7720
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7667
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7667
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7645
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7645
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7628
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7628
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7621
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7621
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7599
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7599
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7502
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7502
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7471
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7471
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7455
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7455
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7447
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7447
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7426
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7426
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7394
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7394
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7377
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7377
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7371
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7371
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7357
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7357
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7338
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7338
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7336
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7336
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7332
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7332
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7331
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7331
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7300
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7300
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7234
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7234
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7214
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7214
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7211
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7211
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7203
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7203
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7202
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7202
Protein translocase subunit SecA P10408 SECA_ECOLI Escherichia coli 3 0.7179
Protein translocase subunit SecA P10408 SECA_ECOLI Escherichia coli 3 0.7179
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7162
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7162
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7157
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7157
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7157
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7157
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7149
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7149
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7136
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7136
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7129
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7129
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7118
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7118
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7108
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7108
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7103
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7103
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7097
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7097
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7080
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7080
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7074
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7074
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7073
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7073
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7064
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7064
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7059
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7059
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7046
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7046
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7001
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7001

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