3,5-dihydroxy-7,8-dimethoxy-3-(3',4'-dimethoxybenzyl)-4-chromanone - Compound Card

3,5-dihydroxy-7,8-dimethoxy-3-(3',4'-dimethoxybenzyl)-4-chromanone

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3,5-dihydroxy-7,8-dimethoxy-3-(3',4'-dimethoxybenzyl)-4-chromanone

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae: Hyacinthoideae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Homoisoflavonoid
Canonical Smiles COc1ccc(cc1OC)CC1(O)COc2c(C1=O)c(O)cc(c2OC)OC
InChI InChI=1S/C20H22O8/c1-24-13-6-5-11(7-14(13)25-2)9-20(23)10-28-18-16(19(20)22)12(21)8-15(26-3)17(18)27-4/h5-8,21,23H,9-10H2,1-4H3
InChIKey QYPNTDKLFDXUFX-UHFFFAOYSA-N
Formula C20H22O8
HBA 8
HBD 2
MW 390.39
Rotatable Bonds 6
TPSA 103.68
LogP 1.98
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 390.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pseudoprospero firmifolium Hyacinthaceae: Hyacinthoideae Plantae 208145

Showing of synonyms

  • Koorbanally C, Sewjee S, et al. (2007). Homoisoflavanones from Pseudoprospero firmifolium of the monotypic tribe Pseudoprospereae (Hyacinthaceae: Hyacinthoideae). Phytochemistry, 2007, 68(22-24), 2753–2756. [View]
Pubchem: 90848764

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(C2=O)COc(c23)cccc3

Level: 1

Mol. Weight: 390.39 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 390.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 390.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.790
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.090
Plasma Protein Binding
49.73
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
Non-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
6.960
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.970
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.040
Micronucleos
Toxic
NR-AhR
Safe
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
-5.810
Rat (Acute)
2.230
Rat (Chronic Oral)
2.790
Fathead Minnow
4.800
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
417.460
Hydration Free Energy
-8.010
Log(D) at pH=7.4
2.920
Log(P)
2.19
Log S
-4.02
Log(Vapor Pressure)
-7.46
Melting Point
151.67
pKa Acid
6.9
pKa Basic
1.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9837
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9371
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9090
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9061
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9030
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8983
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8979
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8973
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8915
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8913
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8834
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8675
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8673
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8672
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8657
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8616
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8544
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8533
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8496
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8437
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8436
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8429
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8428
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8354
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8336
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8325
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8304
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8264
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8238
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8213
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8210
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8181
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8180
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8165
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8164
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8161
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8147
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8145
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8137
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8129
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8104
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8044
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8011
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8005
Calmodulin-like domain protein kinase isoenzyme gamma, related F0V9W9 F0V9W9_NEOCL Neospora caninum 3 0.7979
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7956
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7951
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7941
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7940
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7931
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 4 0.7930
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7893
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7881
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7856
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7803
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7796
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7759
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7731
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7710
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7650
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7645
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7629
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7619
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7612
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7611
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7601
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7589
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7587
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7577
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7522
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7507
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7492
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7487
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7466
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7445
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7426
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7425
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7413
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7407
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7405
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7397
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7392
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7376
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7373
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7369
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 3 0.7360
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7350
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7346
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7344
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7341
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.7340
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7339
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 3 0.7338
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7332
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7328
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7317
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7315
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7296
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7293
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7292
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7287
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7281
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7267
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7261
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7248
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7245
Endoplasmic reticulum aminopeptidase 2 Q6P179 ERAP2_HUMAN Homo sapiens 2 0.7238
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7233
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7224
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7219
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7208
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7208
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7183
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7180
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7178
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7175
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7172
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7172
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7163
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7156
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7153
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7150
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7146
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7146
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7142
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7139
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7132
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7123
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7122
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7098
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7098
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7097
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7094
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7093
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7089
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7089
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7088
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7080
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7078
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7076
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7059
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7055
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7050
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7049
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7047
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7045
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.7040
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7039
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7033
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7029
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7028
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7015
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7010
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7006
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 3 0.7004
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7002

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