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Kaempferol-3-O-{[beta-D-xylopyranosyl(1→3)-alpha-L-rhamnopyranosyl(1→6)][alpha-L-rhamnopyranosyl(1→2)]}-beta-D-4-trans-p-coumaroylgalactopyranoside

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Tetraglycoside

Canonical Smiles	Oc1ccc(cc1)/C=C/C(=O)OC1C(COC2OC(C)C(C(C2O)OC2OCC(C(C2O)O)O)O)OC(C(C1O)OC1OC(C)C(C(C1O)O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(cc1)O
InChI	InChI=1S/C47H54O25/c1-17-30(54)34(58)36(60)46(66-17)72-43-37(61)40(69-28(53)12-5-19-3-8-21(48)9-4-19)27(16-64-45-38(62)41(31(55)18(2)65-45)70-44-35(59)32(56)25(52)15-63-44)68-47(43)71-42-33(57)29-24(51)13-23(50)14-26(29)67-39(42)20-6-10-22(49)11-7-20/h3-14,17-18,25,27,30-32,34-38,40-41,43-52,54-56,58-62H,15-16H2,1-2H3/b12-5+
InChIKey	CQYVNGUVLUBVKE-LFYBBSHMSA-N
Formula	C₄₇H₅₄O₂₅
HBA	25
HBD	13
MW	1018.92
Rotatable Bonds	13
TPSA	393.34
LogP	-2.11
Number Rings	8
Number Aromatic Rings	4
Heavy Atom Count	72
Formal Charge	0
Fraction CSP3	0.49
Exact Mass	1018.3
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Astragalus caprinus	Leguminosae/Fabaceae	Plantae	1042474

Showing of synonyms

Semmar N, Fenet B, et al. (2002). New Flavonol Tetraglycosides from Astragalus caprinus. Chemical & pharmaceutical bulletin, 2002, 50(7), 981-4. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)C(OC5CCCCO5)CC(OC(=O)C=Cc6ccccc6)C4COC(OCC7)CC7OC8CCCCO8

Level: 6

Mol. Weight: 1018.92 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(O3)C(OC4CCCCO4)CC(OC(=O)C=Cc5ccccc5)C3COC(OCC6)CC6OC7CCCCO7

Level: 5

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CC(OC4CCCCO4)C(O2)Oc(c5=O)c(-c6ccccc6)oc(c57)cccc7

Level: 5

Mol. Weight: 1018.92 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CCC(OC(=O)C=Cc5ccccc5)C4COC(OCC6)CC6OC7CCCCO7

Level: 5

Mol. Weight: 1018.92 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OCC3CCC(OC4CCCCO4)C(O3)Oc(c5=O)c(-c6ccccc6)oc(c57)cccc7

Level: 5

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CC(OC4CCCCO4)C(O2)Oc(c5=O)coc(c56)cccc6

Level: 4

Mol. Weight: 1018.92 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCC(OC(=O)C=Cc4ccccc4)C3COC(OCC5)CC5OC6CCCCO6

Level: 4

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CCC(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC3CCCCO3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 1018.92 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OCC3CCC(OC4CCCCO4)C(O3)Oc(c5=O)coc(c56)cccc6

Level: 4

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(CC(CO2)OC3CCCCO3)C2COC(OCC4)CC4OC5CCCCO5

Level: 4

Mol. Weight: 1018.92 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 1018.92 g/mol

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

Level: 4

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CCC(O2)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC3CCCCO3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 1018.92 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 1018.92 g/mol

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

Level: 3

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CC(CO2)OC4CCCCO4

Level: 3

Mol. Weight: 1018.92 g/mol

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

Level: 3

Mol. Weight: 1018.92 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 1018.92 g/mol

SMILES: O1CCCCC1OC(CO2)CCC2COC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 1018.92 g/mol

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

Level: 2

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC3CCCCO3

Level: 2

Mol. Weight: 1018.92 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC3CCCCO3

Level: 2

Mol. Weight: 1018.92 g/mol

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

Level: 2

Mol. Weight: 1018.92 g/mol

SMILES: O1CCCCC1OCC2CCC(CO2)OC3CCCCO3

Level: 2

Mol. Weight: 1018.92 g/mol

SMILES: O1CCCCC1COC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 1018.92 g/mol

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

Level: 1

Mol. Weight: 1018.92 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 1018.92 g/mol

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

Level: 1

Mol. Weight: 1018.92 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1018.92 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1018.92 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1018.92 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 1018.92 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1018.92 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1018.92 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.53
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 87184.620
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 11394881.44

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.710
Plasma Protein Binding: -15.66
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: 6.490
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -265013.030
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.520
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.050
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: -20681156718.050
Rat (Acute): 2.520
Rat (Chronic Oral): 45.290
Fathead Minnow: 26105559.130
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 2326048362.770
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1286.280
Log(P): 0.69
Log S: -5.61
Log(Vapor Pressure): -76595555.46
Melting Point: 252.0
pKa Acid: -558047.43
pKa Basic: -4476.54

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8843
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8310
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8186
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7683
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7173
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7161

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