Luteolin-7,3’,4’-trimethyl ether - Compound Card

Luteolin-7,3’,4’-trimethyl ether

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Luteolin-7,3’,4’-trimethyl ether

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles OCC1O[C@@H](Oc2cc(OC)cc3c2c(=O)cc(o3)c2ccc(c(c2)OC)OC)C([C@H]([C@@H]1O)O)O
InChI InChI=1S/C24H26O11/c1-30-12-7-17-20(18(8-12)34-24-23(29)22(28)21(27)19(10-25)35-24)13(26)9-15(33-17)11-4-5-14(31-2)16(6-11)32-3/h4-9,19,21-25,27-29H,10H2,1-3H3/t19?,21-,22+,23?,24-/m1/s1
InChIKey VCKHKFVWKVWGMH-HSQINTTRSA-N
Formula C24H26O11
HBA 11
HBD 4
MW 490.46
Rotatable Bonds 7
TPSA 157.28
LogP 0.66
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 490.15
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Borago officinalis Boraginaceae Plantae 13363

Showing of synonyms

  • Zemmouri H, Ammar S, et al. (2014). Chemical composition and antioxidant activity of Borago officinalis L. leaf extract growing in Algeria. Arabian Journal of Chemistry,2014,in press. [View]
Pubchem: 44258392
Nmrshiftdb2: 70034538

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cccc3OC4CCCCO4

Level: 2

Mol. Weight: 490.46 g/mol

Structure

SMILES: O=c1ccoc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 490.46 g/mol

Structure

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

Level: 1

Mol. Weight: 490.46 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 490.46 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 490.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 490.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.08
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.14
Plasma Protein Binding
76.43
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
3.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.79
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.42
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
-371.47
Rat (Acute)
2.62
Rat (Chronic Oral)
3.56
Fathead Minnow
5.0
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
531.68
Hydration Free Energy
-3.08
Log(D) at pH=7.4
1.72
Log(P)
0.61
Log S
-4.06
Log(Vapor Pressure)
-11.0
Melting Point
197.1
pKa Acid
7.41
pKa Basic
2.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.9479
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.9479
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9465
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9465
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9454
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9454
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9297
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9297
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8948
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8948
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8772
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8772
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8717
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8717
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8707
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8707
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8636
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8636
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8511
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8511
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8427
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8427
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8413
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8413
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8351
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8351
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8311
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8311
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8194
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8194
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8189
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8189
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8068
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8068
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8056
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8056
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8003
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8003
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.8000
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.8000
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7960
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7960
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7862
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7862
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7829
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7829
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7806
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7806
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7759
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7759
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7690
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7690
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7636
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7636
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7608
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7608
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7606
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7606
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7585
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7585
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7575
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7575
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7574
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7574
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7536
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7536
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7534
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7534
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7505
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7505
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7495
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7495
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7490
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7490
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7443
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7443
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7438
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7438
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7425
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7425
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7415
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7415
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.7407
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.7407
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7400
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7400
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7380
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7380
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7332
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7332
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7324
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7324
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7266
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7266
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7241
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7241
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7209
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7209
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7202
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7202
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7153
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7153
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7148
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7148
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 3 0.7136
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 3 0.7136
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7110
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7110
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7095
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7095
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7093
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7093
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7082
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7082
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 4 0.7064
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 4 0.7064
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7058
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7058
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7034
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7034
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7020
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7020
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7017
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7017
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7013
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7013
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7004
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7004
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7004
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7004

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