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Kaempferol-3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnopyranoside

Family: Plantae - Chenopodiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O[C@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(38-9)39-12-6-13(30)16-14(7-12)40-24(10-2-4-11(29)5-3-10)25(19(16)33)42-27-23(37)21(35)18(32)15(8-28)41-27/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
InChIKey	JYXSWDCPHRTYGU-QHWHWDPRSA-N
Formula	C₂₇H₃₀O₁₅
HBA	15
HBD	9
MW	594.52
Rotatable Bonds	6
TPSA	249.2
LogP	-1.74
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	594.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chenopodium murale	Chenopodiaceae	Plantae	46091

Showing of synonyms

Gohar AA, Maatooq GT, et al. (2000). Two flavonoid glycosides from Chenopodium murale. Phytochemistry,2000,53(2),299-303. [View] [PubMed]

Pubchem: 25202803

Zinc: ZINC000059066262

Chebi: 139409

Nmrshiftdb2: 60026653

No compound-protein relationship available.

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

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

Level: 2

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.55
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.320
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 6.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.870
Plasma Protein Binding: 77.59
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: 7.130
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.690
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.030
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.340
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: -9482.480
Rat (Acute): 2.310
Rat (Chronic Oral): 4.380
Fathead Minnow: 20.710
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 500.600
Hydration Free Energy: -2.990
Log(D) at pH=7.4: -0.370
Log(P): -0.67
Log S: -4.42
Log(Vapor Pressure): -12.72
Melting Point: 221.13
pKa Acid: 3.69
pKa Basic: 5.96

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.9104
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.9104
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8753
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8753
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8564
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8564
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8483
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8483
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8198
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8198
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8095
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8095
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8038
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8038
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7974
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7974
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7937
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7937
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7870
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7870
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7783
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7783
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7688
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7688
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7652
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7652
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7585
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7585
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7444
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7444
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7427
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7427
Interstitial collagenase	P03956	MMP1_HUMAN	Homo sapiens	4	0.7388
Interstitial collagenase	P03956	MMP1_HUMAN	Homo sapiens	4	0.7388
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7368
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7368
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7296
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7296
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7296
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7296
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	5	0.7292
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	5	0.7292
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7241
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7241
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7145
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7145
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7095
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7095
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7090
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7090
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7079
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7079
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7071
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7071
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7013
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7013

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