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Genistin
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Isoflavone Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)occ(c3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1 |
| InChIKey | ZCOLJUOHXJRHDI-CMWLGVBASA-N |
| Formula | C21H20O10 |
| HBA | 10 |
| HBD | 6 |
| MW | 432.38 |
| Rotatable Bonds | 4 |
| TPSA | 170.05 |
| LogP | 0.05 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 432.11 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rosmarinuseriocalyx | Lamiaceae | Plantae | — |
Showing of synonyms
Genistin
529-59-9
Genistine
Genistoside
Genistein 7-glucoside
Glucosyl-7-genistein
Genistein 7-O-beta-D-glucoside
Genistein glucoside
CHEBI:27514
Genistein, 7-O-beta-D-glucoside
1POG3SCN5T
NSC 5112
Genistein, 7-beta-D-glucopyranoside
Glucopyranoside, genistein-7, beta-D-
BRN 0064479
GENISTIN [USP-RS]
4',5,7-trihydroxyisoflavone 7-D-glucoside
GENISTEIN GENISTIN [MI]
5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
DTXSID3022324
4-18-00-02732 (Beilstein Handbook Reference)
NSC-5112
5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
Isoflavone, 4',5,7-trihydroxy-, 7-D-glucoside
4',5,7-Trihydroxyisoflavone 7-.beta.-D-glucopyranoside
GENISTIN (USP-RS)
GENISTEIN 7-O-.BETA.-D-GLUCOPYRANOSIDE
4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-
GENISTIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
Genistein 7-O-.beta.-D-glucoside
5,4'-DI-HYDROXYISOFLAVONE-7-O-.BETA.-D-GLUCOPYRANOSIDE
Genistin (8CI)
4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-
5-hydroxy-3-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-4-one
5-hydroxy-3-(4-hydroxyphenyl)-7-((2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-4-one
5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
GENISTEIN GENISTIN
DTXCID002324
GENISTEIN 7-O-BETA-D-GLUCOPYRANOSIDE
GENISTIN (CONSTITUENT OF SOY ISOFLAVONES)
4',5,7-TRIHYDROXYISOFLAVONE 7-BETA-D-GLUCOPYRANOSIDE
5,4'-DI-HYDROXYISOFLAVONE-7-O-BETA-D-GLUCOPYRANOSIDE
4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-(9CI)
610-921-5
Genisteol 7-monoglucoside
Genistein 7-O-glucoside
MFCD00016883
4H-1-Benzopyran-4-one,7-(b-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-
5-hydroxy-3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
UNII-1POG3SCN5T
Genistin?
Genistein-7-O-beta-D-glucopyranoside
7-O-.beta.-D-glucopyranosyl genistein
4',5,7-Trihydroxyisoflavone 7-glucoside
Genistin (Standard)
SCHEMBL62148
Genistin, analytical standard
MLS006010735
BIDD:ER0520
CHEMBL486625
MEGxp0_000436
ACon1_001495
HY-N0595R
Genistin - CAS 529-59-9
Genistin, >=97.5% (TLC)
GLXC-06732
HY-N0595
MSK40177
BDBM50025609
AKOS025146960
CCG-208377
CS-4240
MG08126
NCGC00163559-01
NCGC00163559-02
NCGC00180447-01
AS-11684
DA-53547
SMR003929926
G0358
C09126
Genistin, primary pharmaceutical reference standard
Q5533221
BRD-K51391729-001-01-4
Genistin, from Glycine max (soybean), >=95% (HPLC)
Genistin, United States Pharmacopeia (USP) Reference Standard
GenistinGenistine
7-(?-D-Glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran- 4-one
4,5,7-Trihydroxyisoflavone 7-?-D-glucoside
Genistein-7 -O-?-D-glucopyranoside
Pubchem:
5281377
Cas:
529-59-9
Gnps:
CCMSLIB00006377431
Zinc:
ZINC000004097913
Kegg Ligand:
C09126
Chebi:
27514
Nmrshiftdb2:
60023801
Chembl:
CHEMBL486625
Comptox:
DTXSID3022324
Bindingdb:
50025609
CPRiL:
34148
SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)-c4ccccc4
Level: 2
Mol. Weight: 432.38 g/mol
SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3
Level: 1
Mol. Weight: 432.38 g/mol
SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3
Level: 1
Mol. Weight: 432.38 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 432.38 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 432.38 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 432.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.62
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.270
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 0.43
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.970
- Plasma Protein Binding
- 86.74
- 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
- 11.180
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.380
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.950
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.720
- 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
- -51.970
- Rat (Acute)
- 2.520
- Rat (Chronic Oral)
- 4.000
- Fathead Minnow
- 4.050
- 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
- 575.270
- Hydration Free Energy
- -5.550
- Log(D) at pH=7.4
- 0.890
- Log(P)
- 0.67
- Log S
- -3.9
- Log(Vapor Pressure)
- -12.87
- Melting Point
- 215.9
- pKa Acid
- 5.26
- pKa Basic
- 6.47
| 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 | 0.9670 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9498 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.9486 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.9401 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 3 | 0.9262 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 5 | 0.9243 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9107 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.9098 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9072 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.9049 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.9045 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.9017 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8917 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.8843 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8787 |
| TetR family transcriptional regulator | Q58L87 | Q58L87_MYCSM | Mycolicibacterium smegmatis | 3 | 0.8765 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8660 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.8569 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8567 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8564 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8341 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 4 | 0.8330 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8249 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8215 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.8096 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8074 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8045 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8001 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.7960 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7956 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7936 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7925 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7903 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 4 | 0.7899 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7891 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7843 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7808 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7805 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7789 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7760 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7758 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7712 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7710 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7659 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7655 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7641 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7635 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7621 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7586 |
| Aldehyde dehydrogenase, mitochondrial | P05091 | ALDH2_HUMAN | Homo sapiens | 4 | 0.7582 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7568 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 3 | 0.7550 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7485 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7478 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7478 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7438 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7425 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7420 |
| Tau-tubulin kinase 1 | Q5TCY1 | TTBK1_HUMAN | Homo sapiens | 3 | 0.7420 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7383 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7360 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7359 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7353 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.7332 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 2 | 0.7325 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7300 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7265 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7254 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7250 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7240 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7233 |
| Cholinesterase | P06276 | CHLE_HUMAN | Homo sapiens | 3 | 0.7231 |
| Calmodulin-like domain protein kinase isoenzyme gamma, related | F0V9W9 | F0V9W9_NEOCL | Neospora caninum | 3 | 0.7202 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 2 | 0.7200 |
| Ribonuclease TTHA0252 | Q5SLP1 | RNSE_THET8 | Thermus thermophilus | 3 | 0.7193 |
| C-1-tetrahydrofolate synthase, cytoplasmic | P11586 | C1TC_HUMAN | Homo sapiens | 3 | 0.7191 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7188 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7185 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 4 | 0.7176 |
| Beta sliding clamp | P0A988 | DPO3B_ECOLI | Escherichia coli | 3 | 0.7172 |
| Ketimine reductase mu-crystallin | O54983 | CRYM_MOUSE | Mus musculus | 2 | 0.7159 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7102 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7081 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 3 | 0.7081 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7078 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7069 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7063 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7045 |
| Cysteine synthase | P45040 | CYSK_HAEIN | Haemophilus influenzae | 3 | 0.7045 |
| Hygromycin-B 4-O-kinase | P00557 | KHYB_ECOLX | Escherichia coli | 3 | 0.7032 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7022 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7007 |