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Kaempferol-3-O-alpha-L-rhamnopyranosyl-(1→6)-]-beta-D-glucopyranoside

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

Canonical Smiles	OC[C@H]1OC(O[C@@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(cc3)O)[C@@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C26H28O16/c27-7-13-15(31)17(33)19(35)24(39-13)41-26-21(37)18(34)20(36)25(42-26)40-23-16(32)14-11(30)5-10(29)6-12(14)38-22(23)8-1-3-9(28)4-2-8/h1-6,13,15,17-21,24-31,33-37H,7H2/t13-,15-,17+,18+,19-,20-,21-,24?,25-,26-/m1/s1
InChIKey	KPOVALBVCPBMHU-MQQQLUACSA-N
Formula	C₂₆H₂₈O₁₆
HBA	16
HBD	10
MW	596.49
Rotatable Bonds	6
TPSA	269.43
LogP	-2.46
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	596.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fraxinus oxycarba	Oleaceae	Plantae	38871

Showing of synonyms

Hosny M (1998). Secoiridoid glucosides from Fraxinus oxycarba. Phytochemistry,1998,47(8),1569-1576. [View]

Pubchem: 162817141

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCC(O4)OC5CCCCO5

Level: 3

Mol. Weight: 596.49 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCC(O3)OC4CCCCO4

Level: 2

Mol. Weight: 596.49 g/mol

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

Level: 2

Mol. Weight: 596.49 g/mol

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

Level: 1

Mol. Weight: 596.49 g/mol

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

Level: 1

Mol. Weight: 596.49 g/mol

SMILES: O1CCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 596.49 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 596.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 596.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 596.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.47
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.59
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 7.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.75
Plasma Protein Binding: 62.8
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: 8.26
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.63
Biodegradation: Toxic
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: 5.15
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: -9342.67
Rat (Acute): 2.31
Rat (Chronic Oral): 4.21
Fathead Minnow: 19.12
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: 533.26
Hydration Free Energy: -2.94
Log(D) at pH=7.4: -0.91
Log(P): -0.29
Log S: -4.45
Log(Vapor Pressure): -12.09
Melting Point: 213.14
pKa Acid: 3.27
pKa Basic: 8.65

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9336
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9336
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8961
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8961
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8936
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8936
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8893
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8893
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8760
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8760
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8707
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8707
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8584
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8584
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8498
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8498
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8390
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8390
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8355
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8355
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8315
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8315
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8296
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8296
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8267
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8267
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.8239
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.8239
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8091
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8091
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8040
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8040
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8026
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8026
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7896
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7896
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7892
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7892
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7783
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7783
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7713
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7713
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7708
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7708
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7638
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7638
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7618
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7618
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7597
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7597
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7575
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7575
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7533
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7533
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7483
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7483
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7472
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7472
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7455
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7455
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7453
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7453
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7437
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7437
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7396
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7396
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7391
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7391
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7320
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7320
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7253
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7253
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7243
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7243
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7233
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7233
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7230
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7230
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7227
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7227
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7200
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7200
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7181
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7181
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7173
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7173
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7169
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7169
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7129
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7129
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7114
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7114
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7110
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7110
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7096
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7096
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7093
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7093
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7079
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7079
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7078
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7078
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7041
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7041
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7012
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7012
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7008
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7008
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7005
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7005

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