Patuletin 3-O-alpha-L-rhamnosyl (1→6)-beta-D-galactoside - Compound Card

Patuletin 3-O-alpha-L-rhamnosyl (1→6)-beta-D-galactoside

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Patuletin 3-O-alpha-L-rhamnosyl (1→6)-beta-D-galactoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles COc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(c(c1)O)O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C28H32O17/c1-8-16(32)20(36)22(38)27(42-8)41-7-14-17(33)21(37)23(39)28(44-14)45-26-19(35)15-13(6-12(31)25(40-2)18(15)34)43-24(26)9-3-4-10(29)11(30)5-9/h3-6,8,14,16-17,20-23,27-34,36-39H,7H2,1-2H3/t8-,14+,16-,17-,20+,21-,22+,23+,27+,28-/m0/s1
InChIKey MLOJYABWNDVJMG-GBWWRXBVSA-N
Formula C28H32O17
HBA 17
HBD 10
MW 640.55
Rotatable Bonds 7
TPSA 278.66
LogP -1.68
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 640.16
Number of Lipinski Rule Violations 3
# 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: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 640.55 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 640.55 g/mol

Structure

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

Level: 2

Mol. Weight: 640.55 g/mol

Structure

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

Level: 1

Mol. Weight: 640.55 g/mol

Structure

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

Level: 1

Mol. Weight: 640.55 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 640.55 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 640.55 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 640.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 640.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.63
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.310
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
20.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.730
Plasma Protein Binding
68.15
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
12.840
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.660
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.950
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.230
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
-34119.340
Rat (Acute)
2.240
Rat (Chronic Oral)
4.460
Fathead Minnow
60.170
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
341.500
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-0.730
Log(P)
-0.34
Log S
-5.06
Log(Vapor Pressure)
-19.21
Melting Point
226.07
pKa Acid
3.35
pKa Basic
6.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9703
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9703
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9077
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9077
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8902
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8902
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8870
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8870
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8784
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8784
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8775
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8775
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8671
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8671
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8559
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8559
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8513
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8513
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8505
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8505
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8471
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8471
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8448
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8448
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8412
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8412
Lethal factor P15917 LEF_BACAN Bacillus anthracis 4 0.8405
Lethal factor P15917 LEF_BACAN Bacillus anthracis 4 0.8405
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8380
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8380
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8348
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8348
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8342
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8342
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8342
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8342
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8272
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8272
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8271
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8271
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8197
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8197
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8154
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8154
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8141
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8141
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8121
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8121
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8028
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8028
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8003
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8003
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7906
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7906
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7898
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7898
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7872
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7872
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7851
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7851
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7830
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7830
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7821
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7821
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7816
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7816
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7748
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7748
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7727
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7727
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7717
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7717
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7710
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7710
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7702
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7702
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7650
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7650
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7524
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7524
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7519
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7519
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7495
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7495
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7487
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7487
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7475
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7475
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7460
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7460
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7443
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7443
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7435
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7435
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7425
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7425
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7413
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7413
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7380
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7380
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7377
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7377
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7368
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7368
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7357
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7357
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7296
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7296
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7295
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7295
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7294
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7294
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7276
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7276
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7267
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7267
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7221
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7221
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7217
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7217
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7169
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7169
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7165
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7165
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7144
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7144
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7120
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7120
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7108
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7108
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7096
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7096
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7095
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7095
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7091
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7091
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7078
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7078
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7047
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7047
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7043
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7043
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7040
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7040
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7019
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7019

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