Luteolin-O-acetylhexoside - Compound Card

Luteolin-O-acetylhexoside

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Luteolin-O-acetylhexoside

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles OCC1OC(Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)O)C(C(C1OC(=O)C)O)O
InChI InChI=1S/C23H22O12/c1-9(25)32-22-18(8-24)35-23(21(31)20(22)30)33-11-5-14(28)19-15(29)7-16(34-17(19)6-11)10-2-3-12(26)13(27)4-10/h2-7,18,20-24,26-28,30-31H,8H2,1H3
InChIKey UTRGEKJNKNMLKI-UHFFFAOYSA-N
Formula C23H22O12
HBA 12
HBD 6
MW 490.42
Rotatable Bonds 5
TPSA 196.35
LogP 0.33
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 490.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ammoides atlantica Apiaceae Plantae 386050

Showing of synonyms

  • Benteldjoune M, Boudiar T, et al. (2021). Antioxidant activity and characterization of flavonoids and phenolic acids of Ammoides atlantica by RP–UHPLC– ESI–QTOF–MS. Nat Prod Res, 2021, 35(10), 1639-1643.. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 490.42 g/mol

Structure

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

Level: 1

Mol. Weight: 490.42 g/mol

Structure

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

Level: 1

Mol. Weight: 490.42 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 490.42 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 490.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 490.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.75
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.08
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.99
Plasma Protein Binding
27.19
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
13.99
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.82
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.8
Micronucleos
Toxic
NR-AhR
Toxic
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
-267.39
Rat (Acute)
2.35
Rat (Chronic Oral)
3.63
Fathead Minnow
4.53
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
593.55
Hydration Free Energy
-3.53
Log(D) at pH=7.4
1.22
Log(P)
0.97
Log S
-4.56
Log(Vapor Pressure)
-10.6
Melting Point
213.7
pKa Acid
6.44
pKa Basic
5.29
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 0.9650
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9393
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9337
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9151
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9057
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8972
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8923
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8902
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8897
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8894
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8664
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8645
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8622
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8616
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8609
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8598
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8526
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8465
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8452
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8437
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8409
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8406
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8400
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8363
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8346
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8275
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8261
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8216
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8212
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8208
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8186
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8166
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8162
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.8078
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8056
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8024
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8017
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7966
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7953
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7942
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7888
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7875
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7874
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7873
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7843
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7809
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7775
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7771
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7765
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7761
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7755
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7748
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7737
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7736
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7732
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7704
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7696
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7693
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7642
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7631
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7617
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7590
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7576
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7570
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7517
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7516
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7514
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7510
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7476
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 3 0.7469
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7461
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7448
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7445
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7438
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7420
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7416
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7413
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7410
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7405
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7400
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7382
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7364
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7353
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7343
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7338
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7327
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7319
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7304
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7297
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7293
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7282
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7282
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7273
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7266
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 3 0.7266
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7256
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7230
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7220
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7215
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7214
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7212
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7210
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7200
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7195
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7180
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7180
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7174
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7165
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7164
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7143
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7135
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7134
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7128
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7112
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7110
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7108
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7103
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7097
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7096
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7095
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7088
Ribosomal RNA large subunit methyltransferase J P37634 RLMJ_ECOLI Escherichia coli 4 0.7088
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7087
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7085
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7074
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7072
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7071
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7069
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7067
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7063
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7062
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7061
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7055
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7050
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7037
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7033
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7023
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7015
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7006
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7000

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