Kaempferol 3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnoside - Compound Card

Kaempferol 3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnoside

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Kaempferol 3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Resedaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OC[C@@H]1O[C@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)c2ccc(cc2)O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(38-9)39-12-6-13(30)16-14(7-12)40-24(10-2-4-11(29)5-3-10)25(19(16)33)42-27-23(37)21(35)18(32)15(8-28)41-27/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 JYXSWDCPHRTYGU-RRLDSZORSA-N
Formula C27H30O15
HBA 15
HBD 9
MW 594.52
Rotatable Bonds 6
TPSA 249.2
LogP -1.74
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 Rorippa palustris Arabideae Plantae 50498
2 Reseda villosa Resedaceae Plantae 415837

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]
  • Berrahal D, Kabouche A, et al. (2006). Flavonoid glycosides from Reseda villosa (Resedaceae). Biochemical Systematics and Ecology, 2006, 34(10), 777-779. [View]

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 594.52 g/mol

Structure

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

Level: 2

Mol. Weight: 594.52 g/mol

Structure

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

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: O=c1ccoc(c12)cc(cc2)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: 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)
-6.54
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.320
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
6.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
77.2
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
7.160
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.630
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.030
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.340
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
-9482.200
Rat (Acute)
2.310
Rat (Chronic Oral)
4.380
Fathead Minnow
20.770
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
500.150
Hydration Free Energy
-2.990
Log(D) at pH=7.4
-0.370
Log(P)
-0.33
Log S
-4.42
Log(Vapor Pressure)
-12.81
Melting Point
228.71
pKa Acid
3.69
pKa Basic
5.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9233
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8259
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8078
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7997
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7952
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7932
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7718
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7554
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7483
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7395
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7326
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7317
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7215
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7157
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7122
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7085
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7049
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7014

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