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Kaempferol-3,7-di-O-beta-glucopyranoside

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

Canonical Smiles	OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)O[C@H]2OC(CO)[C@H](C(C2O)O)O)c2ccc(cc2)O)C([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-11-5-12(31)16-13(6-11)40-24(9-1-3-10(30)4-2-9)25(19(16)34)43-27-23(38)21(36)18(33)15(8-29)42-27/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14?,15?,17-,18-,20+,21?,22?,23?,26-,27-/m1/s1
InChIKey	XFFQVRFGLSBFON-KOPUBOKJSA-N
Formula	C₂₇H₃₀O₁₆
HBA	16
HBD	10
MW	610.52
Rotatable Bonds	7
TPSA	269.43
LogP	-2.77
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	610.15
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Oligomeris linifolia	Resedaceae	Plantae	265230
2	Tribulus pentandrus	Tribulaceae	Plantae	1965241

Showing of synonyms

Saleh NAM, Ahmed AA, et al. (1982). Flavonoid glycosides of Tribulus pentandrus and T. terrestris. Phytochemistry,1982,21(8),1995-2000. [View]
Hussein SR, Elkhateeb A, et al. (2013). Phytochemical investigation of Oligomeris linifolia (Vahl) Macbr. (Resedaceae). Biochemical Systematics and Ecology,2013,49,73-76. [View]

Pubchem: 44258810

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 610.52 g/mol

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

Level: 2

Mol. Weight: 610.52 g/mol

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

Level: 2

Mol. Weight: 610.52 g/mol

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

Level: 2

Mol. Weight: 610.52 g/mol

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

Level: 1

Mol. Weight: 610.52 g/mol

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

Level: 1

Mol. Weight: 610.52 g/mol

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

Level: 1

Mol. Weight: 610.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 610.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.46
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.37
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 11.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.77
Plasma Protein Binding: 49.45
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: 5.65
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.21
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.99
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.65
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: -16090.51
Rat (Acute): 2.43
Rat (Chronic Oral): 4.4
Fathead Minnow: 34.19
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: 458.37
Hydration Free Energy: -2.93
Log(D) at pH=7.4: -0.92
Log(P): -1.32
Log S: -3.89
Log(Vapor Pressure): -16.17
Melting Point: 244.78
pKa Acid: 3.06
pKa Basic: 7.78

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9475
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9475
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8853
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8853
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8579
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8579
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8362
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8362
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8232
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8232
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.8169
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.8169
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7977
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7977
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7853
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7853
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7807
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7807
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7797
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7797
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	0.7775
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7775
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7530
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7530
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7525
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7525
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7431
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7431
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.7371
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.7371
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7250
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7250
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7196
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7196
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7093
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7093
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	4	0.7043
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	4	0.7043
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7008
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7008

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