6-hydroxyluteolin - Compound Card

6-hydroxyluteolin

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6-hydroxyluteolin

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles Oc1ccc(cc1O)c1cc(=O)c2c(o1)cc(c(c2O)O)O
InChI InChI=1S/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H
InChIKey VYAKIUWQLHRZGK-UHFFFAOYSA-N
Formula C15H10O7
HBA 7
HBD 5
MW 302.24
Rotatable Bonds 1
TPSA 131.36
LogP 1.99
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 302.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ficus microcarpa Moraceae Plantae 66385

Showing of synonyms

  • Hassan H.A, Abdelmohsen U.R, et al. (2022). Potential of Ficus microcarpa metabolites against SARS-CoV-2 main protease supported by docking studies.. Natural product research, 2022, 36(4), 994-998. [View]
Pubchem: 5281642
Kegg Ligand: C10072
Chebi: 2197
Nmrshiftdb2: 60025740
Bindingdb: 50412291
CPRiL: 266488
Structure

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

Level: 1

Mol. Weight: 302.24 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 302.24 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 302.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.79
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.370
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.790
Plasma Protein Binding
97.09
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Non-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
10.930
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.190
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.520
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.580
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.810
Rat (Acute)
2.420
Rat (Chronic Oral)
3.530
Fathead Minnow
3.970
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
525.110
Hydration Free Energy
-11.440
Log(D) at pH=7.4
1.820
Log(P)
2.23
Log S
-2.84
Log(Vapor Pressure)
-9.66
Melting Point
349.43
pKa Acid
5.27
pKa Basic
8.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9703
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9594
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9249
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9108
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8954
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8954
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8932
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8911
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.8824
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8824
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8807
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.8773
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.8761
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8752
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8697
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8685
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8646
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8603
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8575
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8567
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8563
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8509
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8507
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8496
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8490
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8484
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8477
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8433
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8429
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8403
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8395
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.8328
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8318
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8312
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8312
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8308
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8287
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8282
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8281
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8266
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8242
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8220
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8218
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8199
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8197
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8185
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8170
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8165
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8140
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.8115
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8076
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.8066
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8038
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8029
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8012
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8006
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8005
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.7959
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7957
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7924
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 4 0.7881
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7874
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7844
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7840
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7837
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7822
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7821
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7818
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7806
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7794
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7783
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7781
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7774
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7759
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7756
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7726
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7725
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7708
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7695
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7694
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7689
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7683
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7680
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7678
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7652
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7650
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7649
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7639
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7626
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7615
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7603
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7569
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7552
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7536
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7496
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7482
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7475
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7466
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7461
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7445
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7435
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7434
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7422
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7413
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7410
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7386
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7383
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 5 0.7368
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7363
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7348
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7341
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7340
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7339
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7328
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7327
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7323
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7318
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7301
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.7294
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7290
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7286
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7272
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7249
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7249
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7248
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7234
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7223
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7223
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7220
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7220
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 4 0.7207
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7201
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7197
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7196
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7194
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7183
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7180
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7176
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7160
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7143
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7139
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7113
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7111
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7100
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7097
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7088
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7088
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7077
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7062
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7050
Serine/threonine-protein kinase MRCK beta Q9Y5S2 MRCKB_HUMAN Homo sapiens 4 0.7050
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7043
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7034
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 5 0.7029
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7020
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7015
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7010
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7008
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7006

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