Luteolin 7,4'-di-O-glucoside - Compound Card

Luteolin 7,4'-di-O-glucoside

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Luteolin 7,4'-di-O-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)OC2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C27H30O16/c28-7-17-20(33)22(35)24(37)26(42-17)39-10-4-12(31)19-13(32)6-15(40-16(19)5-10)9-1-2-14(11(30)3-9)41-27-25(38)23(36)21(34)18(8-29)43-27/h1-6,17-18,20-31,33-38H,7-8H2/t17-,18-,20-,21-,22+,23+,24-,25-,26-,27?/m1/s1
InChIKey CFVDPAXOTMTQCU-XKJPHSEHSA-N
Formula C27H30O16
HBA 16
HBD 10
MW 610.52
Rotatable Bonds 7
TPSA 269.43
LogP -2.77
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 610.15
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Ficus natalensis Moraceae Plantae 309307

Showing of synonyms

  • Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(cc3=O)-c4ccc(cc4)OC5CCCCO5

Level: 3

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 610.52 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 610.52 g/mol

Structure

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

Level: 1

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 610.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.480
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
10.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
70.49
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
7.100
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-4.480
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.730
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.250
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
-15548.240
Rat (Acute)
2.350
Rat (Chronic Oral)
4.810
Fathead Minnow
33.350
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
470.110
Hydration Free Energy
-3.010
Log(D) at pH=7.4
-0.680
Log(P)
-1.75
Log S
-4.03
Log(Vapor Pressure)
-16.19
Melting Point
264.48
pKa Acid
3.24
pKa Basic
7.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9582
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9582
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9284
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9284
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8557
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8557
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8537
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8537
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8488
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8488
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8383
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8383
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8356
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8356
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8320
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8320
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8240
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8240
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8227
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8227
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8159
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8159
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8074
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8074
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8065
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8065
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8044
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8044
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8017
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8017
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8003
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8003
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8001
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8001
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7946
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7946
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7926
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7926
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7904
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7904
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7874
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7874
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7863
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7863
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7860
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7860
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7857
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7857
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7813
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7813
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7796
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7796
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7779
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7779
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7766
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7766
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7750
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7750
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7714
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7714
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7638
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7638
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7633
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7633
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7579
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7579
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7572
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7572
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7532
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7532
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7531
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7531
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7511
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7511
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7508
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7508
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7481
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7481
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7445
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7445
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7445
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7445
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7353
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7353
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7343
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7343
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7337
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7337
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7310
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7310
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7294
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7294
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7253
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7253
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7251
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7251
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7249
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7249
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7201
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7201
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7201
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7201
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7195
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7195
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7189
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7189
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7178
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7178
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7160
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7160
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7121
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7121
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7110
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7110
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 4 0.7091
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 4 0.7091
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7084
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7084
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7081
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7081
Ribonucleoside-diphosphate reductase large chain 1 P21524 RIR1_YEAST Saccharomyces cerevisiae 3 0.7077
Ribonucleoside-diphosphate reductase large chain 1 P21524 RIR1_YEAST Saccharomyces cerevisiae 3 0.7077
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7065
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7065
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7054
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7054
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7051
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7051
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7043
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7043
dTDP-fucosamine acetyltransferase Q8FBQ3 WECD_ECOL6 Escherichia coli O6:H1 3 0.7021
dTDP-fucosamine acetyltransferase Q8FBQ3 WECD_ECOL6 Escherichia coli O6:H1 3 0.7021

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