Genkwanin 8-C-beta-glucopyranoside - Compound Card

Genkwanin 8-C-beta-glucopyranoside

Select a section from the left sidebar

Genkwanin 8-C-beta-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Arecaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone Glycoside
Canonical Smiles OCC1O[C@@H]([C@H](C([C@@H]1O)O)O)c1c(OC)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O
InChI InChI=1S/C22H22O10/c1-30-14-7-12(26)16-11(25)6-13(9-2-4-10(24)5-3-9)31-21(16)17(14)22-20(29)19(28)18(27)15(8-23)32-22/h2-7,15,18-20,22-24,26-29H,8H2,1H3/t15?,18-,19?,20+,22-/m1/s1
InChIKey HHPLIFSIFJSIBY-OBSFFFLGSA-N
Formula C22H22O10
HBA 10
HBD 6
MW 446.41
Rotatable Bonds 4
TPSA 170.05
LogP 0.39
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 446.12
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Livistona australis Arecaceae Plantae 115491

Showing of synonyms

  • Kassem MES, Shoela S, et al. (2012). A sulphated flavone glycoside from Livistona australis and its antioxidant and cytotoxic activity. Natural Product Research,2012,26(15),1381-1387. [View] [PubMed]
Pubchem: 163013085
Nmrshiftdb2: 70093069

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 446.41 g/mol

Structure

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 446.41 g/mol

Structure

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

Level: 1

Mol. Weight: 446.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 446.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 446.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 446.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.27
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.96
Plasma Protein Binding
76.59
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
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
11.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.84
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.99
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.68
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
-79.39
Rat (Acute)
2.44
Rat (Chronic Oral)
3.95
Fathead Minnow
4.05
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
591.24
Hydration Free Energy
-4.57
Log(D) at pH=7.4
1.2
Log(P)
1.04
Log S
-4.69
Log(Vapor Pressure)
-11.55
Melting Point
204.67
pKa Acid
5.77
pKa Basic
6.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9336
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9336
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9271
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9271
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.9021
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.9021
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8954
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8954
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8689
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8689
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8605
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8605
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8575
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8575
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8456
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8456
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8449
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8449
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8248
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8248
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8148
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8148
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8137
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8137
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8094
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8094
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8092
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8092
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7968
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7968
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7939
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7939
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7920
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7920
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7857
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7857
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7789
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7789
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7772
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7772
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7770
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7770
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7613
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7613
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7609
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7609
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7580
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7580
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7559
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7559
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7548
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7548
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7509
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7509
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7502
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7502
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7413
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7413
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7392
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7392
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7383
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7383
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7366
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7366
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7321
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7321
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7261
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7261
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 4 0.7218
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 4 0.7218
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7212
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7212
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7169
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7169
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7167
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7167
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7120
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7120
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7095
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7095
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7094
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7094
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7091
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7091
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7086
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7086
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7059
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7059
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7040
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7040
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7038
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7038
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7015
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7015
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7005
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7005

Download SDF