Luteolin-6-dirhamnoside - Compound Card

Luteolin-6-dirhamnoside

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Luteolin-6-dirhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Caryophyllaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles O[C@H]1[C@H](O)C(OC(C1[C@]1(O)OC(C)(C)[C@H]([C@H]([C@@H]1O)O)O)(C)C)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O
InChI InChI=1S/C29H34O14/c1-27(2)24(29(40)26(39)22(37)25(38)28(3,4)43-29)21(36)20(35)23(42-27)18-14(33)9-16-17(19(18)34)13(32)8-15(41-16)10-5-6-11(30)12(31)7-10/h5-9,20-26,30-31,33-40H,1-4H3/t20-,21-,22+,23?,24?,25-,26-,29-/m0/s1
InChIKey KSFCQXAGJWTMSR-BZNXTCLOSA-N
Formula C29H34O14
HBA 14
HBD 10
MW 606.58
Rotatable Bonds 3
TPSA 250.97
LogP 0.05
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 606.19
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Pteranthus dichotomus Caryophyllaceae Plantae 325512

Showing of synonyms

  • Atta EM, Nassar AA, et al. (2013). New flavonoid glycoside and pharmacological activities of Pteranthus dichotomus Forssk.. Records of Natural Products,2013,7(2),69-79. [View]
Pubchem: 162947874

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCC(CO4)C5CCCCO5

Level: 3

Mol. Weight: 606.58 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)C3CCC(CO3)C4CCCCO4

Level: 2

Mol. Weight: 606.58 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 606.58 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 606.58 g/mol

Structure

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

Level: 1

Mol. Weight: 606.58 g/mol

Structure

SMILES: C1OCCCC1C2CCCCO2

Level: 1

Mol. Weight: 606.58 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 606.58 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 606.58 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 606.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.44
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
7.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
62.3
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
9.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.73
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.16
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
-7242.4
Rat (Acute)
2.48
Rat (Chronic Oral)
4.63
Fathead Minnow
14.33
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
605.93
Hydration Free Energy
-3.16
Log(D) at pH=7.4
-0.26
Log(P)
1.5
Log S
-4.16
Log(Vapor Pressure)
-11.79
Melting Point
240.25
pKa Acid
2.52
pKa Basic
10.14
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 0.9627
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9627
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9372
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9372
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9306
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9306
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9046
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9046
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8940
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8940
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8905
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8905
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8721
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8721
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8658
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8658
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8481
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8481
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8359
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8359
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8284
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8284
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8274
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8274
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8205
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8205
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8137
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8137
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8129
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8129
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8029
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8029
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7993
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7993
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7949
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7949
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7924
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7924
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7844
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7844
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7771
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7771
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7730
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7730
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7712
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7712
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7697
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7697
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7696
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7696
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7660
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7660
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7625
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7625
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7467
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7467
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7443
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7443
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7421
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7421
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7383
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7383
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7364
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7364
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7341
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7341
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7331
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7331
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7321
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7321
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7308
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7308
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7241
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7241
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7227
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7227
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7197
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7197
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7193
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7193
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7190
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7190
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7190
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7190
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7189
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7189
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7151
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7151
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7128
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7128
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7126
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7126
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7114
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7114
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7089
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7089
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7033
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7033
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7014
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7014

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