Patuletin 3-O-beta-D-galactoside - Compound Card

Patuletin 3-O-beta-D-galactoside

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Patuletin 3-O-beta-D-galactoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)c(c(c3)O)OC)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C22H22O13/c1-32-20-10(26)5-11-13(15(20)28)16(29)21(19(33-11)7-2-3-8(24)9(25)4-7)35-22-18(31)17(30)14(27)12(6-23)34-22/h2-5,12,14,17-18,22-28,30-31H,6H2,1H3/t12-,14+,17+,18-,22+/m1/s1
InChIKey AFBZFRQNKMLRPU-UFJVGALSSA-N
Formula C22H22O13
HBA 13
HBD 8
MW 494.41
Rotatable Bonds 5
TPSA 219.74
LogP -0.53
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 494.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Pallenis spinosa Asteraceae Plantae 73981

Showing of synonyms

  • Ahmed AA, Spaller M, et al. (1992). Flavonoids of Pallenis spinosa (Asteraceae). Biochemical Systematics and Ecology,1992,20(8),785-786. [View]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 494.41 g/mol

Structure

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

Level: 1

Mol. Weight: 494.41 g/mol

Structure

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

Level: 1

Mol. Weight: 494.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 494.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 494.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 494.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.670
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.790
Plasma Protein Binding
78.09
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
15.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.160
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.250
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
-282.010
Rat (Acute)
2.330
Rat (Chronic Oral)
4.300
Fathead Minnow
3.850
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
660.130
Hydration Free Energy
-3.930
Log(D) at pH=7.4
0.000
Log(P)
-0.09
Log S
-4.59
Log(Vapor Pressure)
-12.0
Melting Point
203.75
pKa Acid
4.21
pKa Basic
6.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9690
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9690
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8949
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8949
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8933
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8933
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8872
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8872
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8852
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8852
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8785
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8785
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8737
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8737
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8663
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8663
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8602
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8602
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8596
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8596
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8587
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8587
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8557
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8557
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8487
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8487
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8385
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8385
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8324
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8324
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8247
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8247
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8246
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8246
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8244
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8244
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8240
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8240
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8167
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8167
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8051
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8051
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8049
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8049
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7953
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7953
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7931
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7931
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7904
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7904
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7863
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7863
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7823
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7823
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7769
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7769
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7751
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7751
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7750
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7750
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7720
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7720
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7673
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7673
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7659
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7659
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7561
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7561
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7549
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7549
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7473
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7473
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7468
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7468
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7438
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7438
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7430
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7430
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7415
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7415
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7408
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7408
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7400
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7400
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7376
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7376
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7366
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7366
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7364
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7364
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7337
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7337
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7284
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7284
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7250
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7250
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7234
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7234
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7232
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7232
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7227
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7227
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7183
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7183
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7182
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7182
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7181
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7181
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7173
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7173
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7138
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7138
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7120
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7120
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7107
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7107
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7106
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7106
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7103
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7103
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7099
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7099
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7075
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7075
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7071
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7071
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7053
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7053
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7012
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7012
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7005
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7005

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