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Isorhamnetin 3-O-beta-glucoside

Family: Plantae - Brassicaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	OC[C@@H]1O[C@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16-,18+,19-,22+/m0/s1
InChIKey	CQLRUIIRRZYHHS-CQDSFZKYSA-N
Formula	C₂₂H₂₂O₁₂
HBA	12
HBD	7
MW	478.41
Rotatable Bonds	5
TPSA	199.51
LogP	-0.24
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	478.11
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Diplotaxis harra	Brassicaceae	Plantae	308281

Showing of synonyms

Kassem M.E, Afifi M.S, et al. (2013). Two new flavonol glycosides and biological activities of Diplotaxis harra (Forssk.) Boiss. Natural product research, 2013, 27(24), 2272-80. [View] [PubMed]

Pubchem: 72551443

Zinc: ZINC000043465438

Chebi: 75758

Nmrshiftdb2: 70129272

Metabolights: MTBLC75758

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 478.41 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 478.41 g/mol

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

Level: 1

Mol. Weight: 478.41 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.460
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 1.3

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.860
Plasma Protein Binding: 75.15
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: 14.820
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.410
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.090
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.380
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: -185.180
Rat (Acute): 2.300
Rat (Chronic Oral): 4.230
Fathead Minnow: 3.900
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 631.260
Hydration Free Energy: -3.760
Log(D) at pH=7.4: 0.460
Log(P): 0.31
Log S: -4.67
Log(Vapor Pressure): -11.46
Melting Point: 195.69
pKa Acid: 4.94
pKa Basic: 6.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9140
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9104
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8913
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8901
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8863
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8809
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8779
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8625
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8551
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8539
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.8470
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8399
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8372
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8322
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8285
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8259
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8173
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8084
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8073
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8051
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8049
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7982
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7977
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7972
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7962
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7946
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7914
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7870
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7859
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7839
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7814
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7799
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7772
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7766
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7740
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7713
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7675
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7641
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7606
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7569
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7569
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7527
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7445
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7441
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7434
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7359
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7329
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7278
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7269
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7266
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7253
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7233
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7219
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	5	0.7216
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7206
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7200
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7197
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7184
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7177
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7163
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7153
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7144
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7130
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7122
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7112
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7107
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7031
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7015
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	5	0.7009

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