Genkwanin-6-C-beta-glucopyranoside - Compound Card

Genkwanin-6-C-beta-glucopyranoside

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Genkwanin-6-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)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)O
InChI InChI=1S/C22H22O10/c1-30-13-7-14-16(11(25)6-12(31-14)9-2-4-10(24)5-3-9)19(27)17(13)22-21(29)20(28)18(26)15(8-23)32-22/h2-7,15,18,20-24,26-29H,8H2,1H3/t15?,18-,20?,21+,22+/m1/s1
InChIKey ABRULANJVVJLFI-UGCWOADJSA-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: 162916773
Nmrshiftdb2: 70093068

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 446.41 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)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)
-6.56
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.25
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.97
Plasma Protein Binding
74.98
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
10.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.17
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
-79.7
Rat (Acute)
2.57
Rat (Chronic Oral)
4.11
Fathead Minnow
4.08
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
597.0
Hydration Free Energy
-4.59
Log(D) at pH=7.4
1.05
Log(P)
1.22
Log S
-4.53
Log(Vapor Pressure)
-12.31
Melting Point
217.45
pKa Acid
5.34
pKa Basic
6.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9543
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9543
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9494
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9494
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9146
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9146
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8854
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8854
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8771
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8771
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8770
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8770
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8618
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8618
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8531
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8531
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8481
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8481
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8312
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8312
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8309
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8309
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8280
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8280
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8259
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8259
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8104
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8104
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8009
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8009
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7932
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7932
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7861
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7861
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7756
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7756
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7734
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7734
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7697
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7697
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7605
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7605
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7605
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7605
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7591
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7591
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7533
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7533
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7525
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7525
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7486
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7486
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7468
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7468
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7444
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7444
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7414
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7414
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7406
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7406
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7398
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7398
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7356
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7356
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7325
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7325
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7303
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7303
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7237
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7237
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7162
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7162
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7143
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7143
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7122
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7122
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7103
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7103
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7102
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7102
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7098
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7098
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7077
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7077
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7075
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7075
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7067
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7067
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7064
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7064
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7051
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7051
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7047
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7047
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7043
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7043
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7002
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7002
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7000
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7000

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