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Licoisoflavone A

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

Canonical Smiles	CC(=CCc1c(O)ccc(c1O)c1coc2c(c1=O)c(O)cc(c2)O)C
InChI	InChI=1S/C20H18O6/c1-10(2)3-4-13-15(22)6-5-12(19(13)24)14-9-26-17-8-11(21)7-16(23)18(17)20(14)25/h3,5-9,21-24H,4H2,1-2H3
InChIKey	KCUZCRLRQVRBBV-UHFFFAOYSA-N
Formula	C₂₀H₁₈O₆
HBA	6
HBD	4
MW	354.36
Rotatable Bonds	3
TPSA	111.13
LogP	3.79
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	354.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rhynchosia viscosa	Leguminosae/Fabaceae	Plantae	1908410

Showing of synonyms

Bohni N, Cordero-Maldonado ML, et al. (2013). Integration of Microfractionation, NMR and Zebrafish Screening for the In Vivo Bioassay-Guided Isolation and Quantitative Bioactivity Analysis of Natural Products. PloS one, 2013, 8(5), e64006. [View]

Pubchem: 5281789

Cas: 66056-19-7

Zinc: ZINC000005158963

Kegg Ligand: C10486

Chebi: 28620

Nmrshiftdb2: 60068084

Metabolights: MTBLC28620

Chembl: CHEMBL4061300

Comptox: DTXSID10216256

Pdb Ligand: JU3

CPRiL: 100727

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

Level: 1

Mol. Weight: 354.36 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 354.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.46
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.05
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.93
Plasma Protein Binding: 82.16
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: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.61
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.4
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.31
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.84
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.57
Rat (Acute): 2.4
Rat (Chronic Oral): 3.02
Fathead Minnow: 4.83
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 505.19
Hydration Free Energy: -12.22
Log(D) at pH=7.4: 3.43
Log(P): 5.01
Log S: -5.41
Log(Vapor Pressure): -9.0
Melting Point: 228.55
pKa Acid: 6.08
pKa Basic: 7.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.9427
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9240
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9164
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.9087
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9029
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8932
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8931
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	4	0.8834
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8767
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8707
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8654
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8636
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8544
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8502
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.8440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8365
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.8310
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8308
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8290
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8274
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8271
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8267
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8246
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.8136
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.8123
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8111
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.8110
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8055
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7992
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7989
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7964
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7927
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7895
Bromodomain protein, putative	Q8I240	Q8I240_PLAF7	Plasmodium falciparum	5	0.7881
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7857
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7854
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7786
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	5	0.7748
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7733
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7720
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7715
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7702
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7660
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7637
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7629
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7625
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7581
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7575
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7565
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7530
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7510
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7496
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7408
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7398
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7395
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7393
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7392
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7390
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7386
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7385
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7379
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7329
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	4	0.7322
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7320
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7314
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7307
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7292
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7290
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7261
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7260
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7257
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7252
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7234
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7225
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7206
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7203
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7193
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7190
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7185
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7184
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7166
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7136
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7130
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7130
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7114
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7112
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	4	0.7106
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7103
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	4	0.7102
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7102
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7099
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7095
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7093
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7078
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7065
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7061
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7054
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7044
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7043
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic	P80030	FABI_BRANA	Brassica napus	4	0.7041
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7023
Peptide deformylase 1B, chloroplastic/mitochondrial	Q9FUZ2	DEF1B_ARATH	Arabidopsis thaliana	3	0.7006
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7002

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