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Kaempferol-7-O-alpha-L-rhamnnoside

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

Canonical Smiles	O[C@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)C)Oc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccc(cc1)O
InChI	InChI=1S/C21H20O10/c1-8-15(24)17(26)19(28)21(29-8)30-11-6-12(23)14-13(7-11)31-20(18(27)16(14)25)9-2-4-10(22)5-3-9/h2-8,15,17,19,21-24,26-28H,1H3/t8-,15-,17+,19+,21+/m0/s1
InChIKey	HQNOUCSPWAGQND-VAKOWUOTSA-N
Formula	C₂₁H₂₀O₁₀
HBA	10
HBD	6
MW	432.38
Rotatable Bonds	3
TPSA	170.05
LogP	0.78
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	432.11
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ixora coccinea	Rubiaceae	Plantae	43503

Showing of synonyms

Idowu TO, Ogundaini AO, et al. (2010). Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties. Phytochemistry,2010,71(17–18),2092-2098. [View]

Pubchem: 13940825

Nmrshiftdb2: 60031404

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 432.38 g/mol

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

Level: 1

Mol. Weight: 432.38 g/mol

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

Level: 1

Mol. Weight: 432.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 432.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 432.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 432.38 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -6.61
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.42
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.06
Plasma Protein Binding: 88.96
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: 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: 11.53
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.94
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.97
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.39
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: -43.64
Rat (Acute): 2.39
Rat (Chronic Oral): 3.97
Fathead Minnow: 4.07
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: 573.34
Hydration Free Energy: -6.56
Log(D) at pH=7.4: 0.71
Log(P): 0.63
Log S: -4.32
Log(Vapor Pressure): -10.99
Melting Point: 209.42
pKa Acid: 5.67
pKa Basic: 4.8

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9543
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9236
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.9201
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9158
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9144
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.9078
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9020
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8904
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8845
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8818
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8780
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8750
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.8719
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8628
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8611
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	5	0.8568
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8403
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8379
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8375
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8329
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8318
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8273
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8228
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8220
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8218
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8189
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8138
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8129
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.8120
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8073
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8070
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8070
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8067
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.8038
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.8009
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7980
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7971
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7934
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7923
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7908
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7891
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7882
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7881
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7849
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7790
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7789
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7772
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7757
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7702
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7695
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7689
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7671
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7668
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7659
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7654
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7646
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7633
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7631
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7601
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7593
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7579
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7571
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7540
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7518
Catalase-peroxidase	Q3JNW6	KATG_BURP1	Burkholderia pseudomallei	3	0.7498
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7487
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7467
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7465
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7458
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7405
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7401
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7397
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7371
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7368
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7367
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7347
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7319
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7291
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7291
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7264
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	3	0.7258
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7246
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7244
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7233
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7231
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7207
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7205
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7195
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7173
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.7166
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7161
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7158
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7150
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7150
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	Q08AH3	ACS2A_HUMAN	Homo sapiens	2	0.7147
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7141
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7140
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7138
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7126
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7120
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7112
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	5	0.7110
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7104
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	5	0.7067
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7064
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7063
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7063
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7036
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7034
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7032
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7031
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7017
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7016
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7001

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