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Kaempferol 3-O-(2''-alpha-L-rhamnopyranosyl)-beta-L-arabinopyranoside-7-O-alpha-L- rhamnopyranoside

Family: Plantae - Matthioleae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	Oc1ccc(cc1)c1oc2cc(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)cc(c2c(=O)c1O[C@@H]1OC[C@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O)O
InChI	InChI=1S/C32H38O18/c1-10-19(36)23(40)25(42)30(45-10)47-14-7-15(34)18-17(8-14)48-27(12-3-5-13(33)6-4-12)28(22(18)39)49-32-29(21(38)16(35)9-44-32)50-31-26(43)24(41)20(37)11(2)46-31/h3-8,10-11,16,19-21,23-26,29-38,40-43H,9H2,1-2H3/t10-,11-,16+,19-,20-,21+,23+,24+,25+,26+,29-,30-,31-,32-/m0/s1
InChIKey	WNEKTAXRNDLFBT-VUHWDSCYSA-N
Formula	C₃₂H₃₈O₁₈
HBA	18
HBD	10
MW	710.64
Rotatable Bonds	7
TPSA	287.89
LogP	-2.25
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	50
Formal Charge	0
Fraction CSP3	0.53
Exact Mass	710.21
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Matthiola longipetala subsp. livida	Brassicaceae	Plantae	3723
2	Matthiola livida	Matthioleae	Plantae	691258

Showing of synonyms

Marzouk M.M, Al-Nowaihi A.S.M, et al. (2010). Chemosystematic studies on certain species of the family Brassicaceae(Cruciferae) in Egypt. Biochemical Systematics and Ecology, 2010, 38(4), 680–685.. [View]
Marzouk M, Kawashty S, et al. (2008). Two New Kaempferol Glycosides from <i>Matthiola Longipetala</i> (subsp. <i>livida</i>) (Delile) Maire and Carcinogenic Evaluation of its Extract. Natural Product Communications, 2008, 3(8), 1934578X0800300. [View]

Pubchem: 102229827

No compound-protein relationship available.

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC(OCCC5)C5OC6CCCCO6

Level: 4

Mol. Weight: 710.64 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 710.64 g/mol

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

Level: 3

Mol. Weight: 710.64 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5

Level: 3

Mol. Weight: 710.64 g/mol

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

Level: 2

Mol. Weight: 710.64 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4

Level: 2

Mol. Weight: 710.64 g/mol

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

Level: 2

Mol. Weight: 710.64 g/mol

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

Level: 2

Mol. Weight: 710.64 g/mol

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

Level: 1

Mol. Weight: 710.64 g/mol

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

Level: 1

Mol. Weight: 710.64 g/mol

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

Level: 1

Mol. Weight: 710.64 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 710.64 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 710.64 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 710.64 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 710.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.57
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -3.790
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 256.98

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.820
Plasma Protein Binding: 69.28
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: 7.360
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.460
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.960
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.010
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: -464052.690
Rat (Acute): 2.420
Rat (Chronic Oral): 4.670
Fathead Minnow: 599.140
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: 44636.760
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -0.490
Log(P): -0.43
Log S: -4.66
Log(Vapor Pressure): -1490.42
Melting Point: 238.17
pKa Acid: 1.21
pKa Basic: 3.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8538
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8510
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7907
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7702
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7611
Beta-glucosidase 12	B8AVF0	BGL12_ORYSI	Oryza sativa subsp. indica	3	0.7610
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7421
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7396
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7385
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7328
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7292
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7227

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