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Kaempferol 3-O-alpha-L-rhamnoside-7-O-beta-D-galacturonide

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

Canonical Smiles	Oc1ccc(cc1)c1oc2cc(O[C@@H]3O[C@H](C(=O)O)[C@@H]([C@@H]([C@H]3O)O)O)cc(c2c(=O)c1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
InChI	InChI=1S/C27H28O16/c1-8-15(30)17(32)20(35)26(39-8)42-23-16(31)14-12(29)6-11(7-13(14)41-22(23)9-2-4-10(28)5-3-9)40-27-21(36)18(33)19(34)24(43-27)25(37)38/h2-8,15,17-21,24,26-30,32-36H,1H3,(H,37,38)/t8-,15-,17+,18-,19+,20+,21+,24-,26-,27+/m0/s1
InChIKey	MKGZGCPBKPSTST-HUZJDZSOSA-N
Formula	C₂₇H₂₈O₁₆
HBA	15
HBD	9
MW	608.51
Rotatable Bonds	6
TPSA	266.27
LogP	-1.65
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.41
Exact Mass	608.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Silybum marianum	Asteraceae	Plantae	92921

Showing of synonyms

Ahmed AA, Marry TJ, et al. (1989). Flavonoids of the flowers of Silybum marianum. Phytochemistry,1989,28(6),1751-1753. [View]

Pubchem: 102147829

Cas: 124167-98-2

Nmrshiftdb2: 60029330

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 608.51 g/mol

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

Level: 2

Mol. Weight: 608.51 g/mol

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

Level: 2

Mol. Weight: 608.51 g/mol

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

Level: 2

Mol. Weight: 608.51 g/mol

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

Level: 1

Mol. Weight: 608.51 g/mol

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

Level: 1

Mol. Weight: 608.51 g/mol

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

Level: 1

Mol. Weight: 608.51 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 608.51 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 608.51 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 608.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.73
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.290
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 8.26

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.040
Plasma Protein Binding: 84.55
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: 3.440
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.490
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.810
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.910
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: -13323.180
Rat (Acute): 2.110
Rat (Chronic Oral): 4.920
Fathead Minnow: 27.700
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: 503.440
Hydration Free Energy: -3.030
Log(D) at pH=7.4: -1.770
Log(P): -0.3
Log S: -3.94
Log(Vapor Pressure): -14.77
Melting Point: 237.99
pKa Acid: 2.83
pKa Basic: 6.75

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9508
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9508
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8931
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8931
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8797
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8797
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8287
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8287
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	3	0.8276
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	3	0.8276
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8231
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8231
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8205
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8205
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8168
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8168
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7697
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7697
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7692
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7692
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7673
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7673
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7554
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7554
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7448
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7448
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7430
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7430
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7399
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7399
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	3	0.7391
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	3	0.7391
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7390
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7390
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7216
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7216
Mitogen-activated protein kinase kinase kinase 21	Q5TCX8	M3K21_HUMAN	Homo sapiens	3	0.7140
Mitogen-activated protein kinase kinase kinase 21	Q5TCX8	M3K21_HUMAN	Homo sapiens	3	0.7140
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7038
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7038
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7024
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7024
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7024
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7024
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7016
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7016

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