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Kanzonol U

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Benzofuran
- Subclass: Arylbenzofuran

Canonical Smiles	Oc1ccc2c(c1)oc(c2)c1ccc(c2c1OC(C)(C)C=C2)O
InChI	InChI=1S/C19H16O4/c1-19(2)8-7-13-15(21)6-5-14(18(13)23-19)17-9-11-3-4-12(20)10-16(11)22-17/h3-10,20-21H,1-2H3
InChIKey	SJIZTMNAKZAOTA-UHFFFAOYSA-N
Formula	C₁₉H₁₆O₄
HBA	4
HBD	2
MW	308.33
Rotatable Bonds	1
TPSA	62.83
LogP	4.7
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.16
Exact Mass	308.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erythrina addisoniae	Leguminosae/Fabaceae	Plantae	2590682

Showing of synonyms

Na M, Hoang DM, et al. (2007). Inhibitory effect of 2-arylbenzofurans from Erythrina addisoniae on protein tyrosine phosphatase-1B.. Bioorganic & medicinal chemistry letters,2007, 17(14), 3868-3871. [View] [PubMed]

Pubchem: 10542808

Cas: 178330-48-8

Chebi: 174941

Nmrshiftdb2: 60072541

Chembl: CHEMBL233147

Bindingdb: 50213494

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(c2)-c(ccc3)c(c34)OCC=C4

Level: 1

Mol. Weight: 308.33 g/mol

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 308.33 g/mol

SMILES: c1coc(c12)cccc2

Level: 0

Mol. Weight: 308.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.8
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.760
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.05

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.990
Plasma Protein Binding: 59.56
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: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.790
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 2.050
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.710
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.840
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 3.400
Rat (Acute): 2.200
Rat (Chronic Oral): 2.230
Fathead Minnow: 4.850
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 434.820
Hydration Free Energy: -10.820
Log(D) at pH=7.4: 4.190
Log(P): 5.05
Log S: -5.11
Log(Vapor Pressure): -8.55
Melting Point: 246.59
pKa Acid: 8.56
pKa Basic: 6.06

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9464
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9426
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9189
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9129
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9093
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.9068
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8995
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8739
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8507
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	4	0.8310
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8292
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	4	0.8291
Phosphatidylinositol 3-kinase catalytic subunit type 3	Q8NEB9	PK3C3_HUMAN	Homo sapiens	4	0.8285
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8253
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	4	0.8225
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8207
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8143
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8056
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8029
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.8006
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.7966
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7782
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7772
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7750
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7725
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7718
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.7696
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7689
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7663
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7650
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7624
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7619
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7597
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7569
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7563
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7480
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7473
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7467
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7436
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	5	0.7408
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7403
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	5	0.7397
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7394
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7371
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7349
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7340
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7333
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7329
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7322
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	4	0.7287
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7265
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	2	0.7239
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7223
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7215
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	4	0.7192
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	5	0.7171
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7155
Cytochrome P450 2B4	P00178	CP2B4_RABIT	Oryctolagus cuniculus	4	0.7118
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7117
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7101
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7080
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	5	0.7066
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7045
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7036
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7031
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7013
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7008

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