Sophoraisoflavone A - Compound Card

Sophoraisoflavone A

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Sophoraisoflavone A

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles Oc1cc(O)c2c(c1)occ(c2=O)c1ccc(c2c1OC(C)(C)C=C2)O
InChI InChI=1S/C20H16O6/c1-20(2)6-5-12-14(22)4-3-11(19(12)26-20)13-9-25-16-8-10(21)7-15(23)17(16)18(13)24/h3-9,21-23H,1-2H3
InChIKey RIDRQWKYWXHAOD-UHFFFAOYSA-N
Formula C20H16O6
HBA 6
HBD 3
MW 352.34
Rotatable Bonds 1
TPSA 100.13
LogP 3.76
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 352.09
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: 10383349
Nmrshiftdb2: 60033004

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)occ(c2=O)-c3cccc(c34)C=CCO4

Level: 1

Mol. Weight: 352.34 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 352.34 g/mol

Structure

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 352.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.07
Plasma Protein Binding
74.32
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
5.36
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.96
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
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
1.04
Rat (Acute)
2.47
Rat (Chronic Oral)
2.48
Fathead Minnow
4.77
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
496.86
Hydration Free Energy
-11.4
Log(D) at pH=7.4
3.8
Log(P)
4.57
Log S
-5.72
Log(Vapor Pressure)
-9.15
Melting Point
279.32
pKa Acid
7.81
pKa Basic
5.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9115
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.9101
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9092
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.9056
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9011
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8926
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8681
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8675
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8654
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8628
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8571
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8565
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8441
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8264
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8230
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8173
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8156
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.8151
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8103
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8016
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7907
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7904
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7865
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7863
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7742
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7647
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7616
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7572
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7554
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7505
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7498
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7487
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7411
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7387
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7377
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7355
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7342
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7334
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7321
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7311
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7294
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7260
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7249
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7245
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7236
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7209
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7180
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7129
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7114
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7105
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7060
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7054
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7046

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