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5,4'-dihydroxy-8-methylenehydroxy-[2'',2''-dimethyl-3'',4''-dehydro-pyrano-(1'',4'':-7,6)]isoflavone

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Isoflavone

Canonical Smiles	OCc1c2OC(C)(C)C=Cc2c(c2c1occ(c2=O)c1ccc(cc1)O)O
InChI	InChI=1S/C21H18O6/c1-21(2)8-7-13-17(24)16-18(25)15(11-3-5-12(23)6-4-11)10-26-20(16)14(9-22)19(13)27-21/h3-8,10,22-24H,9H2,1-2H3
InChIKey	YJZULEGLRQGVFQ-UHFFFAOYSA-N
Formula	C₂₁H₁₈O₆
HBA	6
HBD	3
MW	366.37
Rotatable Bonds	2
TPSA	100.13
LogP	3.55
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	366.11
Number of Lipinski Rule Violations	0

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

Showing of synonyms

Nguyen PH, Na M, et al. (2010). New stilbenoid with inhibitory activity on viral neuraminidases from Erythrina addisoniae.. Bioorganic & medicinal chemistry letters,2010, 20(22), 6430-6434. [View] [PubMed]

Pubchem: 50899658

Zinc: ZINC000064513030

Nmrshiftdb2: 70032663

Chembl: CHEMBL1271772

Bindingdb: 50483014

No compound-protein relationship available.

SMILES: O1CC=Cc(c2)c1cc(c23)occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 366.37 g/mol

SMILES: O=c1ccoc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 366.37 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 366.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.86
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.9
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.55

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.08
Plasma Protein Binding: 73.08
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.4
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.39
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.2
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.67
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: -2.59
Rat (Acute): 2.88
Rat (Chronic Oral): 2.54
Fathead Minnow: 4.74
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: 490.44
Hydration Free Energy: -8.91
Log(D) at pH=7.4: 3.36
Log(P): 3.9
Log S: -4.89
Log(Vapor Pressure): -9.59
Melting Point: 247.75
pKa Acid: 7.19
pKa Basic: 4.88

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9545
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9493
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.9216
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.9056
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8986
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.8801
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	5	0.8758
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8633
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8559
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8523
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8442
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8041
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	3	0.7998
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7994
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7961
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7936
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7894
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7731
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7673
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7655
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7643
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7642
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7629
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7585
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7575
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7529
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7507
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7475
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7463
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7457
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7455
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7424
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7366
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7262
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7259
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7258
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7208
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	3	0.7168
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7168
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7160
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7158
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7143
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7104
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.7090
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7070
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7068
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7046
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7029

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