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Excelsanone

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

Canonical Smiles	CC(=CCc1ccc(c2c1occ(c2=O)c1ccc(cc1)O)O)C
InChI	InChI=1S/C20H18O4/c1-12(2)3-4-14-7-10-17(22)18-19(23)16(11-24-20(14)18)13-5-8-15(21)9-6-13/h3,5-11,21-22H,4H2,1-2H3
InChIKey	QEVOKNWAMDKTPT-UHFFFAOYSA-N
Formula	C₂₀H₁₈O₄
HBA	4
HBD	2
MW	322.36
Rotatable Bonds	3
TPSA	70.67
LogP	4.38
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	322.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erythrina excelsa	Leguminosae/Fabaceae	Plantae	2803570

Showing of synonyms

Gbaweng AJY, Daïrou H, et al. (2020). Excelsanone, a new isoflavonoid from Erythrina excelsa (Fabaceae), with in vitro antioxidant and in vitro cytotoxic effects on prostate cancer cells lines.. Natural product research,2020, 34(5), 659-667. [View] [PubMed]

Pubchem: 142238766

No compound-protein relationship available.

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 222.24 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.79
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.57
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.48

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.22
Plasma Protein Binding: 78.36
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 0.9
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.61
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.06
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.49
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 3.54
Rat (Acute): 2.1
Rat (Chronic Oral): 2.36
Fathead Minnow: 5.06
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 443.55
Hydration Free Energy: -10.65
Log(D) at pH=7.4: 3.93
Log(P): 5.23
Log S: -5.45
Log(Vapor Pressure): -8.56
Melting Point: 205.64
pKa Acid: 8.45
pKa Basic: 6.56

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	0.9690
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.9508
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9491
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.9373
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	5	0.9260
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9213
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9104
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.9061
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9020
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.9001
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8954
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.8676
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8605
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8600
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8518
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8485
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8482
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8440
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.8409
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8366
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.8331
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8317
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8298
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8281
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8259
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8259
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8210
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8176
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.8154
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.8134
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8126
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8084
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8077
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.8066
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8051
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8049
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.8007
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7975
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7955
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7938
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7935
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7934
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7922
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7921
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7918
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7892
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7884
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7879
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7864
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7860
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7801
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7787
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7780
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7780
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7777
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7765
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7759
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7758
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7709
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7703
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7673
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7649
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7638
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7638
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7633
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7610
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7609
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7596
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7593
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7583
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7575
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7565
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7560
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7525
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7524
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7524
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7519
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7516
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7506
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7501
Bifunctional dihydrofolate reductase-thymidylate synthase	A7UD81	A7UD81_PLAFA	Plasmodium falciparum	4	0.7500
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7493
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7477
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7452
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7450
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7447
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7443
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7438
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	4	0.7437
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7422
Flavonoid 3-O-glucosyltransferase	A6XNC6	UGFGT_MEDTR	Medicago truncatula	3	0.7422
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7416
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7410
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7409
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7392
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7391
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7390
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7379
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	4	0.7378
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7366
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7359
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7351
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7348
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7344
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7330
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7326
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7318
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7315
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7314
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7313
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7299
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7296
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7291
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7290
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7279
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7264
Phosphodiesterase	Q53I60	Q53I60_TRYCR	Trypanosoma cruzi	4	0.7251
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7250
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7242
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7236
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7228
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7214
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7211
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7207
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7199
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7190
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7186
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7184
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7174
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7158
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7156
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7135
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7124
Calmodulin-like domain protein kinase isoenzyme gamma, related	F0V9W9	F0V9W9_NEOCL	Neospora caninum	3	0.7119
Adenosine monophosphate-protein transferase	Q8ZVF7	Q8ZVF7_PYRAE	Pyrobaculum aerophilum	3	0.7109
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7101
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7096
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7086
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7081
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7075
Corticosteroid-binding globulin	P31211	CBG_RAT	Rattus norvegicus	3	0.7066
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7063
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7060
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7059
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7051
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7048
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7042
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7022
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7022
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7017
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7010
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7007
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7006

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