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Kaempferitin
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | Oc1ccc(cc1)c1oc2cc(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)cc(c2c(=O)c1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O |
|---|---|
| InChI | InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27-/m0/s1 |
| InChIKey | PUPKKEQDLNREIM-QNSQPKOQSA-N |
| Formula | C27H30O14 |
| HBA | 14 |
| HBD | 8 |
| MW | 578.52 |
| Rotatable Bonds | 5 |
| TPSA | 228.97 |
| LogP | -0.72 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 578.16 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cleome species | Capparaceae | Plantae | 25782 |
| 2 | Cleome droserifolia | Capparaceae | Plantae | 511510 |
| 3 | Chenopodium murale | Chenopodiaceae | Plantae | 46091 |
| 4 | Ochradenus baccatus | Resedaceae | Plantae | 264972 |
| 5 | Reseda villosa | Resedaceae | Plantae | 415837 |
| 6 | Rhamnus disperma | Rhamnaceae | Plantae | 1813078 |
| 7 | Ixora coccinea | Rubiaceae | Plantae | 43503 |
Showing of synonyms
Kaempferitin
Lespenefril
Lespedin
Lespenephryl
Kaempferol 3,7-dirhamnoside
Lespenephril
Kaempferol 3,7-bisrhamnoside
Kaempferol-3,7-O-alpha-L-dirhamnoside
UNII-VPV01U3R59
BRN 0073958
KAEMFERITRIN
VPV01U3R59
CHEBI:68883
3,7-Bis((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 3,7-bis((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-
DTXSID90197458
4-18-00-03292 (Beilstein Handbook Reference)
Kaempferol 3,7-di-O-alpha-L-rhamnoside
3,7-bis-(alpha-6-deoxymannopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-deoxy-alpha-L-mannopyranoside
3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-deoxy-alpha-L-mannopyranoside
Kaempferol 3-O-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside
DTXCID00119949
7-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-deoxy-alpha-L-mannopyranoside
Kaempferitrin
482-38-2
Kaempferol-dirhamnoside
CHEMBL251766
5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]chromen-4-one
5-Hydroxy-2-(4-hydroxyphenyl)-3,7-bis(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
Karempferitrin
Kaempferitrin (Standard)
LESPEDIN [WHO-DD]
Kaempferol-3,7-dirhamnoside
SCHEMBL571402
MEGxp0_000567
ACon1_000073
GTPL13277
HY-N0628R
Kaempferitrin, >=97% (NMR)
HY-N0628
BDBM50331856
S9112
AKOS032962036
CCG-270118
Kaempferol-3,7-O-(alpha)-dirhamnoside
NCGC00168820-01
AC-34729
AS-56461
KAEMPFEROL 3,7-DIRHAMNOSIDE [MI]
Kaempferol-3,7-bis-O-alpha-L-rhamnoside
XK161839
DB-326537
CS-0009620
C16981
Q6345965
BRD-K45884135-001-01-5
Kaempferol-3-O-alpha-L-rhamnopyranoside-7-O-alpha-L-rhamnopyranoside
3,7-Bis[(6-Deoxy-?-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
3,4',5,7-Tetrahydroxyflavone 3,7-dirham noside
Grosvenorine II
4H-1-BENZOPYRAN-4-ONE, 3,7-BIS((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5-HYDROXY-2-(4-HYDROXYPHENYL)-
- Fathy HM, Aboushoer MI, et al. (2008). Dolabellane diterpenes from Cleome droserifolia. Natural Product Communications,2008,3(9),1479-1482. [View]
- Idowu TO, Ogundaini AO, et al. (2010). Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties. Phytochemistry,2010,71(17–18),2092-2098. [View]
- Berrahal D, Kabouche A, et al. (2006). Flavonoid glycosides from Reseda villosa (Resedaceae). Biochemical Systematics and Ecology, 2006, 34(10), 777-779. [View]
- Sharaf M, El-Ansari MA, et al. (1997). Flavonoids of four Cleome and three Capparis species.. Biochemical Systematics and Ecology,1997,25(2),161-166. [View]
- Berrehal D, Khalfallah A, et al. (2012). Flavononol glycosides of Reseda arabica (Resedaceae). Records of Natural Products,2012,6(4),68-370.. [View]
- Gohar AA, Elmazar MMA (1997). Isolation of hypotensive flavonoids from Chenopodium species growing in Egypt. Phytotherapy Research,1997,11(8),564-567. [View]
- Mohammed H.A, Abd El-Wahab M.F, et al. (2021). Isolation, Characterization, Complete Structural Assignment,and Anticancer Activities of the Methoxylated Flavonoids from Rhamnus disperma Roots. Molecules, 2021, 26(19), 5827. [View] [PubMed]
Pubchem:
5486199
Cas:
482-38-2
Gnps:
CCMSLIB00005757737
Zinc:
ZINC000004216676
Kegg Ligand:
C16981
Chebi:
68883
Nmrshiftdb2:
60022298
Metabolights:
MTBLC68883
Chembl:
CHEMBL251766
Comptox:
DTXSID90197458
Bindingdb:
50331856
CPRiL:
106674
SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5
Level: 3
Mol. Weight: 578.52 g/mol
SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 578.52 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 578.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 578.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 578.52 g/mol
Antibacterial
Bradycardia
Hypotensive
Absorption
- Caco-2 (logPapp)
- -6.6
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.270
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 3.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.920
- Plasma Protein Binding
- 83.16
- 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
- 8.580
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.200
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.990
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.440
- 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
- -5588.670
- Rat (Acute)
- 2.320
- Rat (Chronic Oral)
- 4.230
- Fathead Minnow
- 13.780
- 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
- 523.340
- Hydration Free Energy
- -3.090
- Log(D) at pH=7.4
- 0.240
- Log(P)
- 0.53
- Log S
- -4.63
- Log(Vapor Pressure)
- -11.84
- Melting Point
- 231.75
- pKa Acid
- 4.46
- pKa Basic
- 4.82
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9440 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9440 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8306 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8306 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8305 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8305 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8245 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8245 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8100 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8100 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7831 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7831 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7793 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7793 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7756 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7756 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7715 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7715 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 4 | 0.7512 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 4 | 0.7512 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7468 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7468 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7414 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7414 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7377 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7377 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7345 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7345 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.7239 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.7239 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 4 | 0.7196 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 4 | 0.7196 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7152 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7152 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 4 | 0.7086 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 4 | 0.7086 |