Kaempferol 3-O-(6''-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside - Compound Card

Kaempferol 3-O-(6''-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside

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Kaempferol 3-O-(6''-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Eucilideae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](CO[C@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)O
InChI InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26-,27-/m0/s1
InChIKey RTATXGUCZHCSNG-RVCYDTIBSA-N
Formula C27H30O15
HBA 15
HBD 9
MW 594.52
Rotatable Bonds 6
TPSA 249.2
LogP -1.39
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 594.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Anastatica hierochuntica Eucilideae Plantae 663965

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]
Pubchem: 122173234
Nmrshiftdb2: 60029704

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 594.52 g/mol

Structure

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

Level: 2

Mol. Weight: 594.52 g/mol

Structure

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

Level: 2

Mol. Weight: 594.52 g/mol

Structure

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

Level: 1

Mol. Weight: 594.52 g/mol

Structure

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

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.67
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.400
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
6.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.830
Plasma Protein Binding
71.67
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
11.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.320
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.940
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.410
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
-9039.220
Rat (Acute)
2.300
Rat (Chronic Oral)
4.520
Fathead Minnow
19.840
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
536.060
Hydration Free Energy
-3.130
Log(D) at pH=7.4
-0.390
Log(P)
0.22
Log S
-4.36
Log(Vapor Pressure)
-13.01
Melting Point
206.65
pKa Acid
3.91
pKa Basic
7.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9777
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9445
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9257
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8952
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8927
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8661
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8576
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8509
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8473
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8428
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8422
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8349
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8330
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8316
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8296
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8258
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8238
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8217
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8129
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8053
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7940
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7935
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7931
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7907
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7898
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7861
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7852
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7818
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7784
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7770
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7762
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7751
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7736
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7723
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7691
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7677
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7660
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7660
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7646
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7643
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7564
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7545
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7533
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7458
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7456
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7360
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7360
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7315
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7307
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7292
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7267
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7267
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7252
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7219
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7216
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7210
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7178
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7126
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7112
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7105
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7102
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7101
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7084
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7072
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7028
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7028
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7002

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