5-O-methylgenistein 7-O-beta-D-glucopyranoside - Compound Card

5-O-methylgenistein 7-O-beta-D-glucopyranoside

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5-O-methylgenistein 7-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Iridaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone Glycoside
Canonical Smiles OCC1O[C@@H](Oc2cc(OC)c3c(c2)occ(c3=O)c2ccc(cc2)O)C([C@H]([C@@H]1O)O)O
InChI InChI=1S/C22H22O10/c1-29-14-6-12(31-22-21(28)20(27)19(26)16(8-23)32-22)7-15-17(14)18(25)13(9-30-15)10-2-4-11(24)5-3-10/h2-7,9,16,19-24,26-28H,8H2,1H3/t16?,19-,20+,21?,22-/m1/s1
InChIKey KSVVGBSBNPMXJF-AKJGCJRBSA-N
Formula C22H22O10
HBA 10
HBD 5
MW 446.41
Rotatable Bonds 5
TPSA 159.05
LogP 0.35
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 0
# Species Family Kingdom NCBI Taxonomy ID
1 Iris tingitana Iridaceae Plantae 292520

Showing of synonyms

  • Farag SF, Takaya Y, et al. (2009). Stilbene glucosides from the bulbs of Iris tingitana. Phytochemistry Letters,2009,2(4),148-151. [View]
Pubchem: 44257327
Nmrshiftdb2: 70109470

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)-c4ccccc4

Level: 2

Mol. Weight: 446.41 g/mol

Structure

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

Level: 1

Mol. Weight: 446.41 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=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

Free radical scavenging

Absorption

Caco-2 (logPapp)
-6.48
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.12
Plasma Protein Binding
77.31
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
7.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.88
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.89
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
-88.62
Rat (Acute)
2.51
Rat (Chronic Oral)
3.67
Fathead Minnow
4.24
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
542.15
Hydration Free Energy
-3.66
Log(D) at pH=7.4
0.75
Log(P)
0.23
Log S
-3.97
Log(Vapor Pressure)
-11.77
Melting Point
204.37
pKa Acid
6.39
pKa Basic
4.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9706
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9706
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9702
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9702
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9548
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9548
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9497
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9497
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9390
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9390
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9173
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9173
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9151
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9151
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9087
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9087
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9051
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9051
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9049
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9049
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9027
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9027
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8965
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8965
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8887
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8887
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8857
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8857
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8851
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8851
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8771
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8771
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8660
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8660
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.8635
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.8635
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8566
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8566
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8272
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8272
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8238
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8238
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.8122
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8122
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.8122
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8122
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8120
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8120
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7971
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7971
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7898
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7898
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7879
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7879
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7819
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7819
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7801
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7801
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7790
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7790
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7729
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7729
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7706
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7706
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7703
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7703
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7653
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7653
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 4 0.7641
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 4 0.7641
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7625
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7625
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7574
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7574
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7570
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7570
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7552
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7552
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7538
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7538
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7533
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7533
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7522
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7522
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7506
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7506
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7494
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7494
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7493
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7493
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7433
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7433
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7413
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7413
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7403
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7403
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7400
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7400
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7397
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7397
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7369
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7369
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7334
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7334
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7330
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7330
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7298
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7298
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7278
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7278
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7254
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7254
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7252
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7252
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7242
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7242
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7240
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7240
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7232
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7232
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7215
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7215
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7214
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7214
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7192
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7192
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7167
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7167
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7165
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7165
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7157
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7157
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7152
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7152
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7141
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7141
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7132
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7132
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7130
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7130
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7106
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7106
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7104
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7104
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7101
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7101
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7090
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7090
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7076
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7076
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7069
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7069
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7059
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7059
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7049
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7049
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7041
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7041
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7022
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7022
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7020
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7020
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7013
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7013
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7006
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7006
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004

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