5,7-dihydroxy-40-methoxyisoflavan-2,4-dione - Compound Card

5,7-dihydroxy-40-methoxyisoflavan-2,4-dione

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5,7-dihydroxy-40-methoxyisoflavan-2,4-dione

Structure
Zoomed Structure
  • Family: Plantae - Caesalpinioideae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavanol
Canonical Smiles COc1ccc(cc1)C1C(=O)Oc2c(C1=O)c(O)cc(c2)O
InChI InChI=1S/C16H12O6/c1-21-10-4-2-8(3-5-10)13-15(19)14-11(18)6-9(17)7-12(14)22-16(13)20/h2-7,13,17-18H,1H3
InChIKey IUWKDLFWTRCFEK-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 2
MW 300.27
Rotatable Bonds 2
TPSA 93.06
LogP 1.99
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 300.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gilbertiodendron dewevrei Caesalpinioideae Plantae 162777

Showing of synonyms

  • Stephanie DM, Stéphane FFY, et al. (2022). Dewerin and gilbertionol two new secondary metabolites from the stem bark of Gilbertiodendron dewevrei (De Wild) J. Leonard.. Natural product research,2022, 36(1), 214-222. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(=O)C(C2=O)c3ccccc3

Level: 1

Mol. Weight: 300.27 g/mol

Structure

SMILES: c1cccc(c12)OC(=O)CC2=O

Level: 0

Mol. Weight: 300.27 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 300.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.210
Plasma Protein Binding
45.18
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.980
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.900
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.150
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.430
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.340
Rat (Acute)
2.540
Rat (Chronic Oral)
2.900
Fathead Minnow
4.450
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
411.960
Hydration Free Energy
-9.810
Log(D) at pH=7.4
2.490
Log(P)
2.61
Log S
-5.82
Log(Vapor Pressure)
-7.66
Melting Point
193.83
pKa Acid
7.28
pKa Basic
4.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9430
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9330
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.9327
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9288
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.9127
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9109
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9106
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9106
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.9015
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9011
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8959
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8865
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8854
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8788
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8771
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8748
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8665
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8580
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8536
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8479
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8431
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8426
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.8411
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8386
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8363
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8357
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8297
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8290
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8260
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8251
Beta-ketoacyl-[acyl-carrier-protein] synthase III Q820T1 FABH_ENTFA Enterococcus faecalis 3 0.8233
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 3 0.8207
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8200
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.8134
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8133
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8094
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8080
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8075
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.8066
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8047
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8036
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7964
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7917
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7917
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7902
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7899
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7880
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7794
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7792
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7788
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7766
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7764
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7699
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7681
UDP-N-acetylglucosamine 1-carboxyvinyltransferase P33038 MURA_ENTCC Enterobacter cloacae subsp. cloacae 3 0.7678
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7676
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7671
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7668
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7662
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7659
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7658
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.7643
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7640
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.7629
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7613
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.7593
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7588
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7570
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7562
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 4 0.7544
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7535
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.7532
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7522
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7521
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7516
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7495
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7469
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7453
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7451
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7427
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7425
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7390
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7389
Pentalenic acid synthase Q825I8 CYP28_STRAW Streptomyces avermitilis 3 0.7388
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7385
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7367
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7362
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7318
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7303
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7260
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7254
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7251
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7245
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7244
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7240
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 3 0.7202
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7194
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7184
Nucleoside diphosphate kinase, cytosolic P22887 NDKC_DICDI Dictyostelium discoideum 3 0.7180
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7171
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7161
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7157
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 3 0.7143
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7140
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7136
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7134
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7130
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7103
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7097
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7092
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7089
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7070
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 3 0.7069
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7052
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7033
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7032
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7028
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7028
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7027
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7022
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7015

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