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Gossypetin-8-O-beta-D-glucoside
- Family: Plantae - Malvaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonol Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2c(O)cc(c3c2oc(c2ccc(c(c2)O)O)c(c3=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C21H20O13/c22-5-11-13(27)15(29)17(31)21(32-11)34-19-10(26)4-9(25)12-14(28)16(30)18(33-20(12)19)6-1-2-7(23)8(24)3-6/h1-4,11,13,15,17,21-27,29-31H,5H2/t11-,13-,15+,17-,21+/m1/s1 |
| InChIKey | SJRXVLUZMMDCNG-KKPQBLLMSA-N |
| Formula | C21H20O13 |
| HBA | 13 |
| HBD | 9 |
| MW | 480.38 |
| Rotatable Bonds | 4 |
| TPSA | 230.74 |
| LogP | -0.83 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 480.09 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Malva sylvestris | Malvaceae | Plantae | 145754 |
Showing of synonyms
Gossypetin-8-O-beta-D-glucoside
Gossypin
652-78-8
NSC 656276
BRN 0071526
Gossypetin 8-O-glucoside
A3Q367XWX9
CHEBI:5525
3,5,7,8,3',4'-Hexahydroxyflavone-8-glucoside
DTXSID60215512
4-18-00-03589 (Beilstein Handbook Reference)
2-(3,4-Dihydroxyphenyl)-8-(beta-D-glucopyranosyloxy)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-(beta-D-glucopyranosyloxy)-3,5,7-trihydroxy-
NSC-656276
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
3,3',4',5,7,8-HEXAHYDROXYFLAVONE 8-GLUCOSIDE
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-1-benzopyran-8-yl beta-D-glucopyranoside
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-chromen-4-one
DTXCID90138003
Gossypetin-8-glucoside
MFCD00017429
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Gossypetin 8-glucoside
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-(.beta.-D-glucopyranosyloxy)-3,5,7-trihydroxy-
UNII-A3Q367XWX9
Gossypin (4)
Gossypin (Standard)
ST057186
CHEMBL402915
SCHEMBL1156121
Gossypin, >=90% (HPLC)
BDBM153264
GLXC-03345
AKOS024282592
HY-125911R
MH11045
MS-28931
HY-125911
CS-0102990
3,3',4',5,7,8-Hexahydroxyflavone-8-glucoside
A1-00786
BRD-K05485208-001-01-1
Q27106791
3,3',4',5,7,8-Hexahydroxy flavone-8-glucoside
2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one
2-(3,4-Dihydroxyphenyl)-8-(beta-D-glucopyranosyloxy)-3,5,7-trihydroxy- 4H-1-benzopyran-4-one, 3,3',4',5,7,8-Hexahydroxyflavone 8-glucoside
R7O
- Nawwar M, El Dein A, et al. (1977). Two New Sulfated Flavonol Glucosides from Leaves of Malva Sylvestris. Phytochemistry, 1977, 16(1), 145-146. [View]
Pubchem:
5281621
Cas:
652-78-8
Gnps:
CCMSLIB00005758273
Zinc:
ZINC000004098515
Kegg Ligand:
C10051
Chebi:
5525
Nmrshiftdb2:
60028729
Metabolights:
MTBLC5525
Chembl:
CHEMBL402915
Comptox:
DTXSID60215512
Pdb Ligand:
R7O
Bindingdb:
153264
CPRiL:
73768
SMILES: O1CCCCC1Oc(ccc2)c(c23)oc(cc3=O)-c4ccccc4
Level: 2
Mol. Weight: 480.38 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)OC3CCCCO3
Level: 1
Mol. Weight: 480.38 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 480.38 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 480.38 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 480.38 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 480.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.4
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -6.260
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 1.91
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.670
- Plasma Protein Binding
- 76.63
- 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
- 13.620
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.770
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.880
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.740
- 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
- -168.620
- Rat (Acute)
- 2.410
- Rat (Chronic Oral)
- 4.350
- Fathead Minnow
- 3.560
- 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
- 688.580
- Hydration Free Energy
- -3.890
- Log(D) at pH=7.4
- -1.340
- Log(P)
- -0.35
- Log S
- -3.69
- Log(Vapor Pressure)
- -12.66
- Melting Point
- 214.29
- pKa Acid
- 4.28
- pKa Basic
- 8.29
| 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 | 0.8986 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.8845 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8684 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8524 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.8521 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8512 |
| Cyclin-dependent kinase 5 | Q00535 | CDK5_HUMAN | Homo sapiens | 5 | 0.8503 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8497 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8490 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 5 | 0.8371 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8364 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8329 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 4 | 0.8315 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.8306 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8122 |
| Flavin-dependent thymidylate synthase | Q9WYT0 | THYX_THEMA | Thermotoga maritima | 4 | 0.8112 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8107 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8091 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.8003 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.8001 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7962 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.7958 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7868 |
| Casein kinase I isoform gamma-3 | Q9Y6M4 | KC1G3_HUMAN | Homo sapiens | 4 | 0.7862 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7767 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7761 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7683 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7656 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7572 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7561 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7545 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7520 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7485 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 5 | 0.7459 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7429 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7419 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7415 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7376 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7374 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7361 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 5 | 0.7356 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7316 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7302 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7259 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 4 | 0.7248 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7232 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.7225 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7166 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7138 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7120 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7109 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7090 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7085 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7084 |
| Ribosomal RNA large subunit methyltransferase J | P37634 | RLMJ_ECOLI | Escherichia coli | 4 | 0.7083 |
| NADPH--cytochrome P450 reductase | P00388 | NCPR_RAT | Rattus norvegicus | 4 | 0.7072 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7036 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7035 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7027 |
| Major strawberry allergen Fra a 1-3 | D0E0C7 | FRA13_FRAAN | Fragaria ananassa | 5 | 0.7009 |
| DNA polymerase theta | O75417 | DPOLQ_HUMAN | Homo sapiens | 4 | 0.7009 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7002 |