Justicidin B - Compound Card

Justicidin B

Select a section from the left sidebar

Justicidin B

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Naphthalide Lignan
Canonical Smiles COc1cc2c(cc1OC)cc1c(c2c2ccc3c(c2)OCO3)C(=O)OC1
InChI InChI=1S/C21H16O6/c1-23-16-7-12-5-13-9-25-21(22)20(13)19(14(12)8-17(16)24-2)11-3-4-15-18(6-11)27-10-26-15/h3-8H,9-10H2,1-2H3
InChIKey RTDRYYULUYRTAN-UHFFFAOYSA-N
Formula C21H16O6
HBA 6
HBD 0
MW 364.35
Rotatable Bonds 3
TPSA 63.22
LogP 3.92
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 364.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 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]
Pubchem: 442882
Kegg Ligand: C10636
Chebi: 6094
Nmrshiftdb2: 60019985
CPRiL: 140135
Structure

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

Level: 1

Mol. Weight: 364.35 g/mol

Structure

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

Level: 0

Mol. Weight: 364.35 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 364.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.0
Human Oral Bioavailability 20%
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
-1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.370
Plasma Protein Binding
74.92
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
Non-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
11.280
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.780
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.120
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
-13.830
Rat (Acute)
2.580
Rat (Chronic Oral)
1.450
Fathead Minnow
5.630
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
495.940
Hydration Free Energy
-5.880
Log(D) at pH=7.4
2.880
Log(P)
3.19
Log S
-5.0
Log(Vapor Pressure)
-8.79
Melting Point
198.93
pKa Acid
9.34
pKa Basic
2.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9146
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9146
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9078
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9078
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9069
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9069
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9016
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9016
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8996
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8996
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8672
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8672
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8635
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8635
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8534
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8534
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8521
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8521
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8514
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8514
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8511
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8511
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8509
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8509
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8486
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8486
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8267
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8267
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8190
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8190
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8184
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8184
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8180
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8180
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8155
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8155
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8108
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8108
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8103
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8103
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8091
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8091
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8073
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8073
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.8024
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.8024
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8010
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8010
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8000
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8000
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7996
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7996
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7900
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7900
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7887
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7887
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7836
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7836
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7766
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7766
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7758
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7758
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7739
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7739
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7735
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7735
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7701
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7701
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7651
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7651
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7605
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7605
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7580
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7580
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7578
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7578
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7545
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7545
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7542
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7542
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7513
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7513
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7497
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7497
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7495
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7495
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7493
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7493
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7486
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7486
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7454
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7454
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7449
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7449
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7447
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7447
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7443
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7443
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7425
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7425
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7375
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7375
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7374
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7374
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7371
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7371
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7341
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7341
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7333
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7333
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7319
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7319
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7306
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7306
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7291
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7291
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7280
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7280
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7271
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7271
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7248
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7248
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7225
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7225
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7216
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7216
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7213
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7213
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7193
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7193
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7188
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7188
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7172
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7172
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7158
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7158
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7133
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7133
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7119
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7119
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7097
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7097
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7080
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7080
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7064
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7064
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7063
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7063
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7052
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7052
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7045
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7045
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7042
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7042
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7041
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7041
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7031
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7031
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7015
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7015

Download SDF