Kaempferol 3-O-[beta-D-glucopyranosyl- (1→4)-alpha-L-rhamnopyranosyl-(1→4)-alpha-L-rhamnopyranosyl-(1→6)-(4 trans-p-coumaroyl)]-beta-D- galactopyranoside
- Family: Plantae - Gentianaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: P-Coumaroyl Flavonol Glycoside
Canonical Smiles | OCC1O[C@@H](OC2C(O)OC(C(C2O)O)OC2C(C)OC(C(C2O)O)OCC2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(cc3)O)[C@H]([C@H]([C@H]2OC(=O)/C=C/c2ccc(cc2)O)O)O)[C@H]([C@H]([C@@H]1O)O)O |
---|---|
InChI | InChI=1S/C47H54O27/c1-16-38(71-47-37(63)33(59)42(43(64)74-47)73-45-34(60)30(56)28(54)24(14-48)68-45)31(57)35(61)44(66-16)65-15-25-40(70-26(53)11-4-17-2-7-19(49)8-3-17)32(58)36(62)46(69-25)72-41-29(55)27-22(52)12-21(51)13-23(27)67-39(41)18-5-9-20(50)10-6-18/h2-13,16,24-25,28,30-38,40,42-52,54,56-64H,14-15H2,1H3/b11-4+/t16?,24?,25?,28-,30+,31?,32-,33?,34+,35?,36+,37?,38?,40+,42?,43?,44?,45+,46+,47?/m1/s1 |
InChIKey | DQVIWXOUHHPIEK-LBUMNOMTSA-N |
Formula | C47H54O27 |
HBA | 27 |
HBD | 15 |
MW | 1050.92 |
Rotatable Bonds | 14 |
TPSA | 433.8 |
LogP | -3.82 |
Number Rings | 8 |
Number Aromatic Rings | 4 |
Heavy Atom Count | 74 |
Formal Charge | 0 |
Fraction CSP3 | 0.49 |
Exact Mass | 1050.29 |
Number of Lipinski Rule Violations | 3 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Centaurium spicatum | Gentianaceae | Plantae | 172074 |
Showing of synonyms
- Allam A, Nafady A, et al. (2016). Two new P-coumaroyl flavonoid glycosides having cytokine increasing activity from Centaurium spicatum L. Phytochemistry Letters, 2016, 17, 144-151. [View]
No compound-protein relationship available.
SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCC(OC(=O)C=Cc4ccccc4)C3COC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7
Level: 5
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CCC(OC(=O)C=Cc5ccccc5)C4COC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8
Level: 6
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CCC(OC(=O)C=Cc5ccccc5)C4COC(OC6)CCC6OC7CCCCO7
Level: 5
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CCCC4COC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7
Level: 5
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCC(OC(=O)C=Cc4ccccc4)C3COC(OC5)CCC5OC6CCCCO6
Level: 4
Mol. Weight: 1050.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CCC(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6
Level: 4
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCCC3COC(OC4)CCC4OC(OC5)CCC5OC6CCCCO6
Level: 4
Mol. Weight: 1050.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC(OC3)CCC3OC(OC4)CCC4OC5CCCCO5
Level: 4
Mol. Weight: 1050.92 g/mol
SMILES: O1CCCCC1OC2CCC(OC2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6
Level: 4
Mol. Weight: 1050.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CCC(O2)Oc(c4=O)coc(c45)cccc5
Level: 3
Mol. Weight: 1050.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 1050.92 g/mol
SMILES: O1CCCCC1OC2CCC(OC2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5
Level: 3
Mol. Weight: 1050.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC(OC3)CCC3OC4CCCCO4
Level: 3
Mol. Weight: 1050.92 g/mol
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 1050.92 g/mol
SMILES: O1CCCCC1COC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4
Level: 3
Mol. Weight: 1050.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 1050.92 g/mol
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 1050.92 g/mol
SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC3CCCCO3
Level: 2
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 1050.92 g/mol
SMILES: O1CCCCC1COC(OC2)CCC2OC3CCCCO3
Level: 2
Mol. Weight: 1050.92 g/mol
SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3
Level: 2
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 1050.92 g/mol
SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 1050.92 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 1050.92 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 1050.92 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 1050.92 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 1050.92 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 1050.92 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.48
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 215488.76
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 28162824.16
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.59
- Plasma Protein Binding
- 2.48
- 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
- 5.51
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Safe
- Bioconcentration Factor
- -654993.78
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.25
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.05
- 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
- -51114160290.85
- Rat (Acute)
- 2.62
- Rat (Chronic Oral)
- 110.25
- Fathead Minnow
- 64520784.74
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 5748918009.17
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -3189.39
- Log(P)
- -0.11
- Log S
- -5.34
- Log(Vapor Pressure)
- -189308879.26
- Melting Point
- 228.54
- pKa Acid
- -1379342.13
- pKa Basic
- -11086.62
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 |
Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8944 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8760 |
Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8532 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8500 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8442 |
Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8406 |
Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.8252 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8085 |
Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.8084 |
Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.8083 |
Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8054 |
Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 6 | 0.8011 |
Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.8002 |
Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7987 |
Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7918 |
HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7841 |
Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7766 |
Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7727 |
Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7714 |
Botulinum neurotoxin type A | P0DPI0 | BXA1_CLOBO | Clostridium botulinum | 3 | 0.7629 |
CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.7585 |
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7583 |
Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7579 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7535 |
Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7482 |
Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 4 | 0.7463 |
Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7376 |
17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7323 |
Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7321 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7314 |
Polymerase acidic protein | P03433 | PA_I34A1 | Influenza A virus | 2 | 0.7255 |
3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7252 |
Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7245 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7181 |
Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7134 |
Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7091 |
3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7063 |
Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7043 |
Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7037 |
Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7029 |
tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.7010 |
Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 3 | 0.7005 |