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Kaempferol 3-O-neohesperidoside
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonol Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C27H30O15/c1-9-17(32)20(35)22(37)26(38-9)42-25-21(36)18(33)15(8-28)40-27(25)41-24-19(34)16-13(31)6-12(30)7-14(16)39-23(24)10-2-4-11(29)5-3-10/h2-7,9,15,17-18,20-22,25-33,35-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,25+,26-,27-/m0/s1 |
| InChIKey | OHOBPOYHROOXEI-JWMUNMLDSA-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-neohesperidoside
Kaempferol 3-neohesperidoside
32602-81-6
Kaempferol-3-O-glucorhamnoside
Kaempferol-3-O-neohesperidoside
3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
3-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
40437-72-7
CHEMBL442988
CHEBI:185334
DTXSID201304657
S3278
S5468
AKOS037514501
CCG-270175
FK66099
HY-107207R
Kaempferol-3-O-glucorhamnoside - 65%
Kaempferol 3-neohesperidoside (Standard)
DA-64693
MS-30567
XK175326
XK175847
HY-107207
CS-0027642
Q63398320
Kaempferol 3-O-?-L-rhamnopyranosyl-(1?2)-?-D-glucopyranoside
3-{[(2S,3R,4S,5S,6R)-4,5-DIHYDROXY-6-(HYDROXYMETHYL)-3-{[(2S,3R,4R,5R,6S)-3,4,5-TRIHYDROXY-6-METHYLOXAN-2-YL]OXY}OXAN-2-YL]OXY}-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMEN-4-ONE
- (2003). Flavonoids from Eriobotrya japonica (Rosaceae) growing in Tunisia. Biochemical Systematics and Ecology, 2003, 31(1), 99-101. [View]
Pubchem:
5318761
Cas:
32602-81-6
Zinc:
ZINC000049823026
Chebi:
185334
Nmrshiftdb2:
60025791
Chembl:
CHEMBL442988
CPRiL:
255667
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCCC4)C4OC5CCCCO5
Level: 3
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC(OCCC3)C3OC4CCCCO4
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: C1OCCCC1OC2CCCCO2
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)
- -6.67
- 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
- 6.79
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.830
- Plasma Protein Binding
- 71.64
- 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
- 12.190
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.910
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.920
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.380
- 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
- -9244.730
- Rat (Acute)
- 2.360
- Rat (Chronic Oral)
- 4.290
- Fathead Minnow
- 20.400
- 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
- 524.690
- Hydration Free Energy
- -3.130
- Log(D) at pH=7.4
- -0.320
- Log(P)
- 0.15
- Log S
- -4.35
- Log(Vapor Pressure)
- -12.97
- Melting Point
- 189.63
- pKa Acid
- 4.1
- pKa Basic
- 6.64
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.9050 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8906 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8820 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.8433 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8307 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8187 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8159 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7989 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7971 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7774 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7718 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7644 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7514 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7475 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7407 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | P49354 | FNTA_HUMAN | Homo sapiens | 3 | 0.7305 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7228 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7080 |