5,7,4'-trihydroxy-6-methoxy-3-O-glucosylflavone - Compound Card

5,7,4'-trihydroxy-6-methoxy-3-O-glucosylflavone

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5,7,4'-trihydroxy-6-methoxy-3-O-glucosylflavone

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)c(c(c3)O)OC)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C22H22O12/c1-31-20-10(25)6-11-13(15(20)27)16(28)21(19(32-11)8-2-4-9(24)5-3-8)34-22-18(30)17(29)14(26)12(7-23)33-22/h2-6,12,14,17-18,22-27,29-30H,7H2,1H3/t12-,14-,17+,18-,22+/m1/s1
InChIKey PMKDGKVUENNUGX-OOVDEOTFSA-N
Formula C22H22O12
HBA 12
HBD 7
MW 478.41
Rotatable Bonds 5
TPSA 199.51
LogP -0.24
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 478.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Haplophyllum tuberculatum Rutaceae Plantae 452784

Showing of synonyms

  • Khalid SA, Waterman PG (1981). Alkaloid, lignan and flavonoid constituents of Haplophyllum tuberculatum from Sudan. Planta Medica,1981,43(2),148-152. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 478.41 g/mol

Structure

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

Level: 1

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.69
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.390
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
79.8
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
13.540
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.310
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.090
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.790
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
-193.020
Rat (Acute)
2.340
Rat (Chronic Oral)
4.190
Fathead Minnow
4.020
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
619.910
Hydration Free Energy
-3.710
Log(D) at pH=7.4
0.470
Log(P)
0.23
Log S
-4.6
Log(Vapor Pressure)
-11.62
Melting Point
202.99
pKa Acid
4.84
pKa Basic
5.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9715
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9715
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9448
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9448
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9034
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9034
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8966
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8966
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8861
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8861
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8854
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8854
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8821
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8821
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8743
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8743
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8736
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8736
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8658
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8658
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8654
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8654
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8576
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8576
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8562
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8562
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8464
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8464
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8461
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8461
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8383
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8383
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8368
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8368
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8325
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8325
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8284
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8284
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8282
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8282
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8244
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8244
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8243
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8243
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8238
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8238
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8157
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8157
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8155
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8155
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8146
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8146
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8133
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8133
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8113
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8113
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8068
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8068
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8056
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8056
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8002
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8002
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7942
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7942
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7900
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7900
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7898
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7898
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7890
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7890
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7830
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7830
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.7764
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.7764
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7746
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7746
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7663
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7663
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7637
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7637
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7626
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7626
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7558
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7558
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7555
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7555
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7527
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7527
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7518
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7518
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7480
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7480
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7474
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7474
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7469
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7469
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7463
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7463
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7462
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7462
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7449
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7449
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7439
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7439
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7410
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7410
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7386
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7386
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7382
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7382
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7365
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7365
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7311
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7311
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7310
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7310
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7262
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7262
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7254
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7254
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7251
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7251
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7244
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7244
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7203
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7203
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7159
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7159
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7155
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7155
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7148
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7148
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7117
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7117
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 4 0.7113
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 4 0.7113
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7110
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7110
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7075
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7075
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7074
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7074
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 4 0.7061
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 4 0.7061
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7058
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7058
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7053
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7053
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7044
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7044
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7032
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7032

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