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Justicidin-A

Family: Rutaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Naphthalide Lignan

Canonical Smiles	COc1cc2c(c3ccc4c(c3)OCO4)c3C(=O)OCc3c(c2cc1OC)OC
InChI	InChI=1S/C22H18O7/c1-24-16-7-12-13(8-17(16)25-2)21(26-3)14-9-27-22(23)20(14)19(12)11-4-5-15-18(6-11)29-10-28-15/h4-8H,9-10H2,1-3H3
InChIKey	ANFSXHKDCKWWDB-UHFFFAOYSA-N
Formula	C₂₂H₁₈O₇
HBA	7
HBD	0
MW	394.38
Rotatable Bonds	4
TPSA	72.45
LogP	3.93
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	394.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Haplophyllum tuberculatum	Rutaceae	Plantae	452784
2	Haplophyllum tuberculatum	Rutaceae	Plantae	452784

Showing of synonyms

Khalid SA, Waterman PG (1981). Alkaloid, lignan and flavonoid constituents of Haplophyllum tuberculatum from Sudan. Planta Medica,1981,43(2),148-152. [View] [PubMed]
Sheriha GM, Abou Amer KM (1984). Lignans of Haplophyllum tuberculatum. Phytochemistry,1984,23(1),151-153. [View]

Pubchem: 159982

Cas: 25001-57-4

Kegg Ligand: C10633

Chebi: 6093

Nmrshiftdb2: 60070682

Chembl: CHEMBL508532

Comptox: DTXSID40179709

CPRiL: 140135

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

Level: 1

Mol. Weight: 304.3 g/mol

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

Level: 0

Mol. Weight: 184.19 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 122.12 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.730
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.340
Plasma Protein Binding: 73.92
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: 10.550
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.830
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.900
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.360
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: -43.270
Rat (Acute): 3.100
Rat (Chronic Oral): 1.640
Fathead Minnow: 5.870
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 507.020
Hydration Free Energy: -4.240
Log(D) at pH=7.4: 3.020
Log(P): 3.47
Log S: -4.9
Log(Vapor Pressure): -8.57
Melting Point: 205.23
pKa Acid: 9.31
pKa Basic: 1.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.9209
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.9209
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9139
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9139
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.9051
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.9051
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9043
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9043
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8879
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8879
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8784
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8784
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8680
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8680
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8597
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8597
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.8537
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.8537
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8526
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8526
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8504
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8504
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8472
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8472
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8414
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8414
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8368
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8368
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8244
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8244
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.8215
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.8215
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8200
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8200
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8176
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8176
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8163
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8163
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8142
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8142
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8115
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8115
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8041
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8041
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8029
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8029
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7994
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7994
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7960
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7960
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7935
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7935
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7882
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7882
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7850
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7850
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7845
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7845
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7838
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7838
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7828
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7828
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7818
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7818
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7668
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7668
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7635
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7635
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7549
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7549
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7546
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7546
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7538
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7538
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7536
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7536
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7525
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7525
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7503
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7503
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7431
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7431
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7413
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7413
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7381
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7381
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7376
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7376
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7366
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7366
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7331
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7331
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7323
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7323
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7284
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7284
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7251
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7251
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7220
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7220
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7205
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7205
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7151
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7151
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7147
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7147
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7141
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7141
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7138
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7138
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7090
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7090
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7089
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7089
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7089
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7089
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7085
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7085
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7051
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7051
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7051
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7051
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7025
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7025

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