7-hydroxy-5-methoxy-6,8-dimethylflavone - Compound Card

7-hydroxy-5-methoxy-6,8-dimethylflavone

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7-hydroxy-5-methoxy-6,8-dimethylflavone

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles COc1c(C)c(O)c(c2c1c(=O)cc(o2)c1ccccc1)C
InChI InChI=1S/C18H16O4/c1-10-16(20)11(2)18-15(17(10)21-3)13(19)9-14(22-18)12-7-5-4-6-8-12/h4-9,20H,1-3H3
InChIKey NXIOJDXYHLKSSC-UHFFFAOYSA-N
Formula C18H16O4
HBA 4
HBD 1
MW 296.32
Rotatable Bonds 2
TPSA 59.67
LogP 3.79
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 296.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Oxyanthus unilocularis Annonaceae Plantae 1768086

Showing of synonyms

  • Kayo MT, Simo MK, et al. (2021). Antifungal potential of extracts, fractions and compounds from Uvaria comperei (Annonaceae) and Oxyanthus unilocularis (Rubiaceae).. Natural product research,2021, 35(24), 5732-5736. [View] [PubMed]
Pubchem: 14753671
Chebi: 70656
Nmrshiftdb2: 60081144
Metabolights: MTBLC70656
Bindingdb: 50482883

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 296.32 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 296.32 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 296.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.370
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.340
Plasma Protein Binding
88.65
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.420
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.770
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.970
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.340
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
4.400
Rat (Acute)
2.150
Rat (Chronic Oral)
1.580
Fathead Minnow
4.870
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
420.000
Hydration Free Energy
-10.230
Log(D) at pH=7.4
3.460
Log(P)
4.14
Log S
-5.01
Log(Vapor Pressure)
-7.24
Melting Point
175.6
pKa Acid
8.27
pKa Basic
4.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9686
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9558
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 4 0.9416
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9323
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9233
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8972
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8874
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8845
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8803
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8797
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8761
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8756
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8712
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8614
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8600
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8541
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8529
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8520
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8492
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8467
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8465
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8463
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8453
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8435
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8428
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8427
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8364
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8357
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8347
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8322
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8309
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8282
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8281
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8266
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8263
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8259
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8248
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8239
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8229
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8195
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8192
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8191
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8188
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8166
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8068
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8057
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8048
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8041
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7990
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7985
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7983
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7980
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7971
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7953
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7937
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7935
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7873
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7844
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7814
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7799
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7785
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7773
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7768
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7744
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7701
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7691
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7656
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7612
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7608
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7598
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7582
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7577
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7574
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7573
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7573
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7542
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7537
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7506
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7495
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7493
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7478
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7461
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7446
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7438
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7433
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7421
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7399
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7396
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7376
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7367
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7361
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7359
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7353
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7353
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7346
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7346
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7334
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7333
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7331
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 4 0.7330
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7324
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7316
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 5 0.7314
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7309
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7296
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7286
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 4 0.7282
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7267
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7253
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7249
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7233
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7229
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7221
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7212
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7165
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7163
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7157
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7126
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7113
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7111
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7100
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7096
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7091
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7084
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7082
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7074
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7069
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7061
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7060
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7057
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.7053
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7050
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7050
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7047
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7035
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7025
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7025

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