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Kaempferol 3-O-alpha-[(6-P-coumaroyl galactopyranosyl-O-beta-(1→4)-O-alpha-rhamnopyranosyl-(1→4)]-O-alpha-rhamnopyranoside

Family: Plantae - Solanaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	O=C(OCC1O[C@@H](O[C@H]2C(C)O[C@H](C([C@H]2O)O)O[C@H]2C(C)O[C@H](C([C@H]2O)O)Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)C([C@H]([C@@H]1O)O)O)/C=C/c1ccc(cc1)O
InChI	InChI=1S/C42H46O21/c1-16-36(32(52)35(55)41(58-16)63-39-29(49)27-23(46)13-22(45)14-24(27)59-38(39)19-6-10-21(44)11-7-19)61-40-34(54)31(51)37(17(2)57-40)62-42-33(53)30(50)28(48)25(60-42)15-56-26(47)12-5-18-3-8-20(43)9-4-18/h3-14,16-17,25,28,30-37,40-46,48,50-55H,15H2,1-2H3/b12-5+/t16?,17?,25?,28-,30+,31-,32-,33?,34?,35?,36+,37+,40+,41+,42+/m1/s1
InChIKey	PJICYRUAMGEBLK-YXFQFQSLSA-N
Formula	C₄₂H₄₆O₂₁
HBA	21
HBD	11
MW	886.81
Rotatable Bonds	11
TPSA	334.42
LogP	-0.57
Number Rings	7
Number Aromatic Rings	4
Heavy Atom Count	63
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	886.25
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Capsicum annum	Solanaceae	Plantae	4072

Showing of synonyms

Allam A.E. (2021). Suppression of cytokine production by newly isolated flavonoids from pepper. Fitoterapia, 2021, 151, 104903. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3CCC(OC3)OC4CCC(OC4)Oc(c5=O)c(-c6ccccc6)oc(c57)cccc7

Level: 5

Mol. Weight: 886.81 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3CCC(OC3)OC4CCC(OC4)Oc(c5=O)coc(c56)cccc6

Level: 4

Mol. Weight: 886.81 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OC4)CCC4OC(OC5)CCC5OC6CCCCO6

Level: 4

Mol. Weight: 886.81 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3CCC(OC3)OC4CCCOC4

Level: 3

Mol. Weight: 886.81 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OC3)CCC3OC(OC4)CCC4OC5CCCCO5

Level: 3

Mol. Weight: 886.81 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OC4)CCC4OC5CCCCO5

Level: 3

Mol. Weight: 886.81 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 886.81 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OC3)CCC3OC4CCCCO4

Level: 2

Mol. Weight: 886.81 g/mol

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

Level: 2

Mol. Weight: 886.81 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 886.81 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 886.81 g/mol

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

Level: 1

Mol. Weight: 886.81 g/mol

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

Level: 1

Mol. Weight: 886.81 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 886.81 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 886.81 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 886.81 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 886.81 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.61
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1062.36
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 139671.32

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.78
Plasma Protein Binding: 43.97
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: 7.88
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -3242.44
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.79
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.05
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: -253492742.72
Rat (Acute): 2.36
Rat (Chronic Oral): 5.16
Fathead Minnow: 319989.41
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 28503246.32
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -2.63
Log(P): 2.51
Log S: -5.76
Log(Vapor Pressure): -938541.48
Melting Point: 247.17
pKa Acid: -6778.15
pKa Basic: -30.15

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9778
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9462
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9288
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8929
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8890
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8857
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8773
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8502
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8473
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8459
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8448
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8334
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8327
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8274
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8235
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8221
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8110
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8043
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8040
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.8039
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.8009
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7994
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7993
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7992
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7980
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7957
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	5	0.7947
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7935
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7909
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7833
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7783
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7767
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7765
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7759
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7746
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7711
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7605
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7601
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7570
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7568
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7471
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7399
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7330
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7293
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7286
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7270
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7243
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7238
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7213
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7179
DNA gyrase subunit B	Q839Z1	GYRB_ENTFA	Enterococcus faecalis	3	0.7175
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7149
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7141
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7130
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7116
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7053
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7044
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7017
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7011

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