Luteolin acetyl-glucuronide - Compound Card

Luteolin acetyl-glucuronide

Select a section from the left sidebar

Luteolin acetyl-glucuronide

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles O=C(Oc1cc(ccc1O)c1cc(=O)c2c(o1)cc(cc2O)O)OC1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C22H18O14/c23-8-4-10(25)15-11(26)6-12(33-14(15)5-8)7-1-2-9(24)13(3-7)34-22(32)36-21-18(29)16(27)17(28)19(35-21)20(30)31/h1-6,16-19,21,23-25,27-29H,(H,30,31)/t16-,17-,18+,19-,21?/m0/s1
InChIKey FZQWTRBOQRGBOM-DAZJWRSOSA-N
Formula C22H18O14
HBA 13
HBD 7
MW 506.37
Rotatable Bonds 4
TPSA 233.65
LogP -0.02
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 506.07
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Rosmarinuseriocalyx Lamiaceae Plantae

Showing of synonyms

  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)Oc(ccc2)cc2-c(cc3=O)oc(c34)cccc4

Level: 2

Mol. Weight: 506.37 g/mol

Structure

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

Level: 1

Mol. Weight: 506.37 g/mol

Structure

SMILES: O1CCCCC1OC(=O)Oc2ccccc2

Level: 1

Mol. Weight: 506.37 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 506.37 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 506.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 506.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.85
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.36
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.1
Plasma Protein Binding
88.59
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
6.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.8
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.8
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
-380.97
Rat (Acute)
2.2
Rat (Chronic Oral)
4.14
Fathead Minnow
4.01
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
637.34
Hydration Free Energy
-3.28
Log(D) at pH=7.4
-0.33
Log(P)
0.65
Log S
-4.31
Log(Vapor Pressure)
-14.38
Melting Point
233.59
pKa Acid
4.82
pKa Basic
6.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9284
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9143
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9089
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9062
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.9042
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.9010
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8973
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8949
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8926
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8902
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8882
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8851
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8826
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8729
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8694
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.8680
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8659
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8595
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8557
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8556
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8527
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8523
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8509
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8509
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8491
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8465
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8456
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8447
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.8443
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8441
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8433
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.8422
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8381
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8352
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8346
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8337
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8331
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8299
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8299
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8277
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8256
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8239
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8212
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8207
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8206
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8152
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8148
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8115
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8085
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8084
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8069
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8050
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8047
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8037
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7982
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7955
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7941
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7928
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 4 0.7923
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7920
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7911
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7896
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7896
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7887
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7861
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7856
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7833
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7832
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7818
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7804
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7787
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7784
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7772
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7756
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 4 0.7727
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7723
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7714
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7686
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7685
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7673
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7646
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7638
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7625
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7618
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7590
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7584
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7574
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7571
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7570
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7564
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7561
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7549
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7535
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7522
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7521
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7513
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7499
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7492
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7467
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7435
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7429
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7428
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7406
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7406
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7399
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7369
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7365
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7360
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7346
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7342
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7329
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7326
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7324
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7324
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7320
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7312
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7312
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 3 0.7304
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7295
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7292
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7290
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7288
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 5 0.7280
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7269
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7260
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7252
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7242
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7237
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7232
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7227
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7210
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7208
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7206
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7191
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7187
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7181
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7177
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7170
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7160
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7157
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7149
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7135
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7133
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7131
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7122
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7120
Cyclin-dependent protein kinase PHO85 P17157 PHO85_YEAST Saccharomyces cerevisiae 4 0.7116
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7111
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7097
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7097
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7088
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7085
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7078
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7076
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7063
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7060
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7058
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7049
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7048
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7037
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7020
Ribosomal protein S6 kinase alpha-1 Q15418 KS6A1_HUMAN Homo sapiens 3 0.7004

Download SDF