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Kaempferol-3-O-(4-beta-D-xylopyranosyl)-alpha-L-rhamnopyranoside-7-O-alpha-L-rhamno-pyranoside

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

Canonical Smiles	OC[C@H]1OC(O[C@@H]2C(O[C@@H]([C@H]([C@@H]2O)O)C)Oc2c(oc3c(c2=O)c(O)cc(c3)OC2O[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/C33H40O19/c1-10-19(37)23(41)26(44)31(46-10)48-14-7-15(36)18-16(8-14)49-28(12-3-5-13(35)6-4-12)29(22(18)40)51-33-30(25(43)20(38)11(2)47-33)52-32-27(45)24(42)21(39)17(9-34)50-32/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10-,11+,17+,19-,20+,21+,23+,24-,25-,26+,27+,30-,31?,32?,33?/m0/s1
InChIKey	JAYRGPGCJWYHLY-NJAWTQSOSA-N
Formula	C₃₃H₄₀O₁₉
HBA	19
HBD	11
MW	740.66
Rotatable Bonds	8
TPSA	308.12
LogP	-2.89
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	52
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	740.22
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chenopodium album	Chenopodiaceae	Plantae	3559

Showing of synonyms

Ibrahim LF, Kawashty SA, et al. (2007). A comparative study of the flavonoids and some biological activities of two Chenopodium species. Chemistry of Natural Compounds,2007,43(1),24-28. [View]

Pubchem: 162950016

Nmrshiftdb2: 60025885

No compound-protein relationship available.

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC(OCCC5)C5OC6CCCCO6

Level: 4

Mol. Weight: 740.66 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 740.66 g/mol

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

Level: 3

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 740.66 g/mol

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

Level: 2

Mol. Weight: 740.66 g/mol

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

Level: 2

Mol. Weight: 740.66 g/mol

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

Level: 2

Mol. Weight: 740.66 g/mol

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

Level: 1

Mol. Weight: 740.66 g/mol

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

Level: 1

Mol. Weight: 740.66 g/mol

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

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 740.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 740.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 740.66 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: -1.19
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 637.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.78
Plasma Protein Binding: 52.7
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: 6.02
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -12.89
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.95
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.29
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: -1153639.32
Rat (Acute): 2.4
Rat (Chronic Oral): 4.8
Fathead Minnow: 1465.89
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: 122887.48
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.88
Log(P): -0.95
Log S: -4.6
Log(Vapor Pressure): -4032.09
Melting Point: 224.95
pKa Acid: -5.49
pKa Basic: 4.89

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8500
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8500
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8291
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8291
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8155
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8155
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7766
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7766
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7613
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7613
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7589
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7589
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7408
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7408
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7272
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7272
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7245
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7245
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7089
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7089

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