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Kaempferol 3-O-beta-isorhamninoside

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

Canonical Smiles	Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1OC(O[C@H]2OC(C)[C@@H]([C@@H](C2O)O)O[C@@H]2OC(C)[C@@H]([C@@H](C2O)O)O)[C@H](C([C@@H]1O)O)O)O
InChI	InChI=1S/C32H38O19/c1-9-17(36)19(38)22(41)29(45-9)48-26-10(2)46-30(25(44)21(26)40)50-32-24(43)20(39)23(42)31(51-32)49-28-18(37)16-14(35)7-13(34)8-15(16)47-27(28)11-3-5-12(33)6-4-11/h3-10,17,19-26,29-36,38-44H,1-2H3/t9?,10?,17-,19-,20?,21+,22?,23-,24-,25?,26-,29-,30+,31+,32?/m0/s1
InChIKey	SGLQLWJUICKESL-LCWLMNFZSA-N
Formula	C₃₂H₃₈O₁₉
HBA	19
HBD	11
MW	726.64
Rotatable Bonds	7
TPSA	308.12
LogP	-2.58
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	51
Formal Charge	0
Fraction CSP3	0.53
Exact Mass	726.2
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: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCC(O4)OC(OC5)CCC5OC6CCCCO6

Level: 4

Mol. Weight: 726.64 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCC(O3)OC(OC4)CCC4OC5CCCCO5

Level: 3

Mol. Weight: 726.64 g/mol

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

Level: 3

Mol. Weight: 726.64 g/mol

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

Level: 2

Mol. Weight: 726.64 g/mol

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

Level: 2

Mol. Weight: 726.64 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCCO3

Level: 2

Mol. Weight: 726.64 g/mol

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

Level: 1

Mol. Weight: 726.64 g/mol

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

Level: 1

Mol. Weight: 726.64 g/mol

SMILES: O1CCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 726.64 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 726.64 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 726.64 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 726.64 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 726.64 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: -3.300
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 371.6

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 43.14
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: 9.060
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -4.660
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.760
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.770
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: -669972.940
Rat (Acute): 2.360
Rat (Chronic Oral): 4.760
Fathead Minnow: 856.910
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: 67298.750
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1.060
Log(P): 0.24
Log S: -4.54
Log(Vapor Pressure): -2248.62
Melting Point: 222.49
pKa Acid: -1.9
pKa Basic: 6.9

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9386
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9184
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8971
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8839
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8730
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8602
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8567
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8508
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8478
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8444
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8363
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8324
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8098
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7856
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7852
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7772
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7760
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7738
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7729
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7706
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7612
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7599
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	5	0.7597
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.7563
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7557
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7500
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7478
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7450
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7374
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	5	0.7359
Seed lectin subunit I	P05045	LEC1_VIGUC	Vigna unguiculata subsp. cylindrica	3	0.7332
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7287
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7281
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7261
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7253
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7215
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7145
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7117
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7086
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7069
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7050
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7042
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7007

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