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Kaempferol 3-O-rutinoside
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonol Glycoside
| Canonical Smiles | Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@H]1O[C@@H](COC2O[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-CWCNIYHWSA-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 | Eriobotrya japonica | Rosaceae | Plantae | 32224 |
Showing of synonyms
Kaempferol 3-O-rutinoside
17650-84-9
Kaempferol-3-O-rutinoside
Nictoflorin
NICOTIFLOROSIDE
Kaempferol-3-rutinoside
Kaempferol 3-Rutinoside
Nicotiflorine
Kaempferol-3-O-beta-rutinoside
Kaempferol 3-O-beta-rutinoside
UNII-4056D20K3H
CHEBI:69657
4056D20K3H
KAEMPFEROL 3-RHAMNOGLUCOSIDE
Flavone, 3,4',5,7-tetrahydroxy-, 3-rhamnoglucoside
KAEMPFEROL 3-beta-RUTINOSIDE
KAEMPFEROL 3-O-beta-D-RUTINOSIDE
KAEMPFEROL-3-O-RUTINOSIDE (CONSTITUENT OF GINKGO)
Nicotiflorin
MFCD03427292
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Kaempferol 3-O-(6''-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside
3-rutinosylkaempferol
5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
Kaempferol 3-O-b -Rutinoside (Nicotiflorin)
Kaempferol 3-O-|A -rutinoside
3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-ss-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
3,4',5,7-Tetrahydroxyflavone 3-rhamnoglucoside
Nicotiflorin (Standard)
Kaempferol 3-O-rutinose
Kaempferol 3-rhamno-glucoside
MLS000563045
SCHEMBL240355
CHEMBL498879
MEGxp0_000024
ACon1_002178
HY-N1475R
Kaempferol 3-O-beta -rutinoside
DTXSID50938804
HMS2268M08
HY-N1475
MSK40328
BDBM50378581
S3267
AKOS032962209
FK65430
KAEMPFEROL 3-.BETA.-RUTINOSIDE
1ST40328
4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
AC-34731
AS-35049
DA-76182
KAEMPFEROL 3-O-.BETA.-RUTINOSIDE
SMR001215820
KAEMPFEROL 3-O-.BETA.-D-RUTINOSIDE
CS-0016975
NS00097624
C21833
Kaempferol 3-O-beta -rutinoside, >=98.0% (HPLC)
Q23058965
KAEMPFEROL-3-O-RUTINOSIDE (CONSTITUENT OF GINKGO) [DSC]
KAEMPFEROL 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSIDE
KAEMPFEROL 3-O-(.ALPHA.-L-RHAMNOPYRANOSYL-(1->6)-.BETA.-D-GLUCOPYRANOSIDE)
KAEMPFEROL 3-O-.BETA.-D-(6''-O-.ALPHA.-L-RHAMNOPYRANOSYL)GLUCOPYRANOSIDE
3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
4H-1-BENZOPYRAN-4-ONE, 3-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
- (2003). Flavonoids from Eriobotrya japonica (Rosaceae) growing in Tunisia. Biochemical Systematics and Ecology, 2003, 31(1), 99-101. [View]
Pubchem:
5318767
Cas:
17650-84-9
Gnps:
CCMSLIB00000222763
Zinc:
ZINC000004349478
Chebi:
69657
Nmrshiftdb2:
60005884
Metabolights:
MTBLC69657
Chembl:
CHEMBL498879
CPRiL:
56846
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 594.52 g/mol
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 594.52 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 594.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 594.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 594.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.7
- 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
- 6.16
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.830
- Plasma Protein Binding
- 68.01
- 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
- 11.890
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.400
- 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
- 5.400
- 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
- -9038.730
- Rat (Acute)
- 2.300
- Rat (Chronic Oral)
- 4.520
- Fathead Minnow
- 19.850
- 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
- 535.360
- Hydration Free Energy
- -3.130
- Log(D) at pH=7.4
- -0.390
- Log(P)
- 0.06
- Log S
- -4.33
- Log(Vapor Pressure)
- -12.87
- Melting Point
- 203.5
- pKa Acid
- 3.91
- pKa Basic
- 7.14
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9774 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9529 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.9326 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9114 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.9019 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8929 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8847 |
| Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 6 | 0.8641 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.8534 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8502 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8437 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8428 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8419 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 3 | 0.8413 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.8314 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8282 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8162 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8079 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.8070 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8048 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.8046 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.8021 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7976 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7976 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7922 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7919 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7850 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7800 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7780 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7755 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7753 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7753 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7722 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7642 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7605 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 4 | 0.7575 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7569 |
| Protein polybromo-1 | Q86U86 | PB1_HUMAN | Homo sapiens | 5 | 0.7567 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7563 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 4 | 0.7507 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7394 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.7346 |
| Glutathione S-transferase F2 | P46422 | GSTF2_ARATH | Arabidopsis thaliana | 3 | 0.7340 |
| Botulinum neurotoxin type A | P0DPI0 | BXA1_CLOBO | Clostridium botulinum | 3 | 0.7326 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 4 | 0.7302 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7273 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7250 |
| DNA topoisomerase 4 subunit B | H7C794 | PARE_ENTFA | Enterococcus faecalis | 3 | 0.7237 |
| Dihydrofolate reductase | P0A017 | DYR_STAAU | Staphylococcus aureus | 4 | 0.7234 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.7233 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7226 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7226 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7191 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 5 | 0.7171 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7156 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7147 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7052 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7052 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7039 |
| DNA gyrase subunit B | Q839Z1 | GYRB_ENTFA | Enterococcus faecalis | 3 | 0.7028 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7007 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7006 |