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 - Compound Card

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

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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

Structure
Zoomed Structure
  • 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.

Structure

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

Structure

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

Structure

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

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CCCC4COC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7

Level: 5

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCC(OC(=O)C=Cc4ccccc4)C3COC(OC5)CCC5OC6CCCCO6

Level: 4

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CCC(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC(O3)CCCC3COC(OC4)CCC4OC(OC5)CCC5OC6CCCCO6

Level: 4

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC(OC3)CCC3OC(OC4)CCC4OC5CCCCO5

Level: 4

Mol. Weight: 1050.92 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2COC3CCCCO3)CCC(O2)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 1050.92 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1050.92 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 1050.92 g/mol

Structure

SMILES: O1CCCCC1COC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 1050.92 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(CCCO2)C2COC3CCCCO3

Level: 2

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 1050.92 g/mol

Structure

SMILES: O1CCCCC1COC(OC2)CCC2OC3CCCCO3

Level: 2

Mol. Weight: 1050.92 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 1050.92 g/mol

Structure

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 1050.92 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1050.92 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1050.92 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 1050.92 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1050.92 g/mol

Structure

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

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