5,6-dihydroxy-2-(4-hydroxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one - Compound Card

5,6-dihydroxy-2-(4-hydroxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one

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5,6-dihydroxy-2-(4-hydroxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol
Canonical Smiles COc1c(oc2c(c1=O)c(O)c(c(c2OC)O)O)c1ccc(cc1)O
InChI InChI=1S/C17H14O8/c1-23-16-11(20)9-10(19)12(21)13(22)17(24-2)15(9)25-14(16)7-3-5-8(18)6-4-7/h3-6,18-19,21-22H,1-2H3
InChIKey CMBVCLGARAHQQY-UHFFFAOYSA-N
Formula C17H14O8
HBA 8
HBD 4
MW 346.29
Rotatable Bonds 3
TPSA 129.59
LogP 2.3
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 346.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cleome arabica Capparaceae Plantae 511509

Showing of synonyms

  • Ladhari A, Tufano I, et al. (2020). Influence of new effective allelochemicals on the distribution of Cleome arabica L. community in nature. Natural product research, 2020, 34(6), 773-781. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 346.29 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 346.29 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 346.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.21
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.230
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.110
Plasma Protein Binding
88.64
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.750
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.700
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.450
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.450
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.530
Rat (Acute)
2.470
Rat (Chronic Oral)
3.380
Fathead Minnow
4.320
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
503.100
Hydration Free Energy
-10.380
Log(D) at pH=7.4
1.750
Log(P)
2.63
Log S
-4.4
Log(Vapor Pressure)
-7.94
Melting Point
223.22
pKa Acid
6.28
pKa Basic
4.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9753
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9288
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9259
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9053
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.9034
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9011
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8973
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8972
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8946
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8936
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8883
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8855
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8841
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8790
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8725
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8677
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8677
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8659
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8625
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8618
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8610
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8608
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8597
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8588
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8582
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 4 0.8570
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8522
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8499
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8498
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8480
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8467
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8450
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8442
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8442
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8440
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8429
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8405
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8401
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8377
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8376
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8365
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8346
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8343
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8341
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8328
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8273
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 3 0.8264
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8264
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8242
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8220
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8212
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8153
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8140
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8140
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8139
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8124
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8116
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8081
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8070
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8061
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8054
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.8045
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8027
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8001
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7968
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7955
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7952
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7944
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7909
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7869
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7859
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7828
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7791
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7751
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7746
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7746
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7720
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7710
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7691
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7675
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7664
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7660
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7637
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7637
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 4 0.7636
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7631
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7630
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7624
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7623
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7612
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7605
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7604
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7585
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7576
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7568
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.7532
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7528
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7525
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7458
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7446
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7436
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7428
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7424
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7411
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7408
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7404
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7403
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7390
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7384
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7383
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7380
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7362
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7351
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7350
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7347
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7342
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7327
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7320
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7318
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7304
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7289
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7268
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7259
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7250
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7249
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7238
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7231
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7216
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7207
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7207
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7204
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7204
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7191
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7183
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7179
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7171
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7156
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7080
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7072
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7053
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7037
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7031
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7024
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7020
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7016
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7013
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7011
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7009
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7004

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