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Kaempferol 3-O-beta-D-rhamninoside

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

Canonical Smiles	Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)[C@@H]([C@@H]([C@H]1O)O)O)O
InChI	InChI=1S/C33H40O19/c1-10-19(37)23(41)25(43)32(48-10)51-29-20(38)11(2)47-31(27(29)45)46-9-17-21(39)24(42)26(44)33(50-17)52-30-22(40)18-15(36)7-14(35)8-16(18)49-28(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-27,29,31-39,41-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24-,25+,26+,27+,29+,31+,32-,33-/m0/s1
InChIKey	UYVBMGULWGRDQT-KABOUGNXSA-N
Formula	C₃₃H₄₀O₁₉
HBA	19
HBD	11
MW	740.66
Rotatable Bonds	8
TPSA	308.12
LogP	-2.54
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	Rhamnus disperma	Rhamnaceae	Plantae	1813078

Showing of synonyms

Marzouk M, El-Toumy S, et al. (1999). Polyphenolic metabolites of Rhamnus disperma. Phytochemistry, 1999, 52(5), 943-946. [View]

Pubchem: 23815364

Cas: 83170-31-4

Gnps: CCMSLIB00000218601

Nmrshiftdb2: 60027151

No compound-protein relationship available.

SMILES: O1CCCCC1OC2CC(OCC2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 740.66 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 740.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 740.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

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: O1CCCCC1COC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)occ(c2=O)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: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: C1COCCC1OC2CCCCO2

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): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -1.610
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 608.77

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.780
Plasma Protein Binding: 63.91
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: 9.050
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -11.490
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.720
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.920
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: -1100848.070
Rat (Acute): 2.470
Rat (Chronic Oral): 4.630
Fathead Minnow: 1398.160
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: 116622.120
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -0.860
Log(P): -
Log S: -4.52
Log(Vapor Pressure): -3830.03
Melting Point: 225.97
pKa Acid: -5.84
pKa Basic: 6.27

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9767
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9290
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9088
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8982
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8934
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8736
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8662
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8581
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8559
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8531
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8506
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8478
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8420
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8190
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8178
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.8132
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8110
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8097
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8064
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8035
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8026
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8009
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8009
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7986
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7933
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7928
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7918
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7900
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7899
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7855
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7810
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7787
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7776
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7756
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7590
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7582
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7549
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7529
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7426
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7385
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7344
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7334
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7319
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7260
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7248
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7211
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7210
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7190
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7188
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7184
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7177
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7174
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7154
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7147
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7140
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7093
DNA gyrase subunit B	Q839Z1	GYRB_ENTFA	Enterococcus faecalis	3	0.7059
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7054
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7053
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7052
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7049
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7044
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7043
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7018
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7008

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