Kaempferol 3-O-rutinoside - Compound Card

Kaempferol 3-O-rutinoside

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Kaempferol 3-O-rutinoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid 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+/m1/s1
InChIKey RTATXGUCZHCSNG-WLPGYADJSA-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 Gomphocarpus sinaicus Apocynaceae Plantae 2291033
2 Tabebuia argentea Bignoniaceae Plantae 3350745
3 Conyza dioscoridis Asteraceae Plantae 264977

Showing of synonyms

  • Heneidak S, Grayer RJ, et al. (2006). Flavonoid glycosides from Egyptian species of the tribe Asclepiadeae (Apocynaceae, subfamily Asclepiadoideae). Biochemical Systematics and Ecology,2006,34(7),575-584. [View]
  • De Abreu B, Temraz A, et al. (2014). Phenolic glycosides from Tabebuia argentea and Catalpa bignonioides. Phytochemistry Letters,2014,7,85-88. [View]
  • Ahmed AA, Meek FR, et al. (1987). Sulfated and non-sulfated flavonoids from Pluchea dioscoridis. Journal of Natural Products,1987,50(2),311. [View]
Pubchem: 20055286
Nmrshiftdb2: 60047889

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)
-6.66
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
6.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.830
Plasma Protein Binding
71.46
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
11.940
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.270
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
-9039.360
Rat (Acute)
2.300
Rat (Chronic Oral)
4.510
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
535.880
Hydration Free Energy
-3.120
Log(D) at pH=7.4
-0.370
Log(P)
0.1
Log S
-4.35
Log(Vapor Pressure)
-13.04
Melting Point
206.35
pKa Acid
3.88
pKa Basic
7.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9741
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9741
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9141
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9141
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8876
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8876
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8734
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8734
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8640
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8640
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8542
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8542
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8214
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8214
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8186
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8186
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8170
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8170
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8142
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8142
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8134
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8134
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8068
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8068
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8042
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8042
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7927
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7927
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7885
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7885
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7864
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7864
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7730
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7730
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7710
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7710
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7623
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7623
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7409
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7409
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7310
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7310
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7309
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7309
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7277
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7277
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7255
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7255
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7213
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7213
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7183
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7183
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7177
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7177
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7145
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7145
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7039
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7039
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7032
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7032

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