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Kaempferol 3-O-alpha-rhamnoside-7-O-beta-D-xylosyl(1→2)-O-alpha-L-rhamnoside

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

Canonical Smiles	C[C@@H]1OC(Oc2ccc(cc2)c2oc3cc(OC4O[C@@H](C)[C@@H]([C@H]([C@H]4O)O)O)cc(c3c(=O)c2O)O)[C@@H]([C@@H]([C@H]1O)O)OC1OC[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C32H38O18/c1-10-19(35)23(39)27(43)31(45-10)48-14-7-15(33)18-17(8-14)49-28(25(41)22(18)38)12-3-5-13(6-4-12)47-32-29(24(40)20(36)11(2)46-32)50-30-26(42)21(37)16(34)9-44-30/h3-8,10-11,16,19-21,23-24,26-27,29-37,39-43H,9H2,1-2H3/t10-,11-,16+,19-,20-,21-,23+,24+,26+,27+,29+,30?,31?,32?/m0/s1
InChIKey	WQBQUTVGOOMOBW-AQHFWPTOSA-N
Formula	C₃₂H₃₈O₁₈
HBA	18
HBD	10
MW	710.64
Rotatable Bonds	7
TPSA	287.89
LogP	-2.25
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	50
Formal Charge	0
Fraction CSP3	0.53
Exact Mass	710.21
Number of Lipinski Rule Violations	3

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

Showing of synonyms

El-Sayed NH, Awaad AS, et al. (1999). A flavonol triglycoside from Chenopodium murale. Phytochemistry,1999,51(4),591-593. [View]

Pubchem: 162985503

Nmrshiftdb2: 60025824

No compound-protein relationship available.

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(cc3=O)-c4ccc(cc4)OC(OCCC5)C5OC6CCCCO6

Level: 4

Mol. Weight: 710.64 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 710.64 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(cc3=O)-c4ccc(cc4)OC5CCCCO5

Level: 3

Mol. Weight: 710.64 g/mol

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

Level: 2

Mol. Weight: 710.64 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 710.64 g/mol

SMILES: c1ccccc1OC(OCCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 710.64 g/mol

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

Level: 1

Mol. Weight: 710.64 g/mol

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

Level: 1

Mol. Weight: 710.64 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 710.64 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 710.64 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 710.64 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 710.64 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 710.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.6
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -3.86
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 259.93

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.82
Plasma Protein Binding: 62.24
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: 6.29
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.54
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.78
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.96
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: -470911.95
Rat (Acute): 2.48
Rat (Chronic Oral): 4.98
Fathead Minnow: 607.3
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: 45452.77
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.76
Log(P): -1.6
Log S: -4.3
Log(Vapor Pressure): -1524.42
Melting Point: 241.58
pKa Acid: 0.93
pKa Basic: 4.27

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9253
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9253
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8795
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8795
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8764
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8764
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8698
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8698
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8579
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8579
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8419
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8419
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.8055
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.8055
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8051
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8051
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8025
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8025
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8011
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8011
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7882
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7882
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7718
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7718
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7692
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7692
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7666
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7666
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7660
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7660
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7629
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7629
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	5	0.7549
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	5	0.7549
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7525
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7525
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7498
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7498
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7448
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7448
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7352
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7352
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7299
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7299
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7245
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7245
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.7058
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.7058
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7015
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7015

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