Kaempferol-3-O-{[beta-D-xylopyranosyl(1→3)-alpha-L-rhamnopyranosyl(1→6)][alpha-L-rhamnopyranosyl(1→2)]}-beta-D-3-trans-feruloylgalactopyranoside - Compound Card

Kaempferol-3-O-{[beta-D-xylopyranosyl(1→3)-alpha-L-rhamnopyranosyl(1→6)][alpha-L-rhamnopyranosyl(1→2)]}-beta-D-3-trans-feruloylgalactopyranoside

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Kaempferol-3-O-{[beta-D-xylopyranosyl(1→3)-alpha-L-rhamnopyranosyl(1→6)][alpha-L-rhamnopyranosyl(1→2)]}-beta-D-3-trans-feruloylgalactopyranoside

Structure
Zoomed Structure
  • Family: Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Tetraglycoside
Canonical Smiles COc1cc(/C=C/C(=O)OC2C(O)C(COC3OC(C)C(C(C3O)OC3OCC(C(C3O)O)O)O)OC(C2OC2OC(C)C(C(C2O)O)O)Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)ccc1O
InChI InChI=1S/C48H56O26/c1-17-31(55)36(60)38(62)47(68-17)74-44-42(71-29(54)11-5-19-4-10-23(51)26(12-19)64-3)34(58)28(16-66-46-39(63)41(32(56)18(2)67-46)72-45-37(61)33(57)25(53)15-65-45)70-48(44)73-43-35(59)30-24(52)13-22(50)14-27(30)69-40(43)20-6-8-21(49)9-7-20/h4-14,17-18,25,28,31-34,36-39,41-42,44-53,55-58,60-63H,15-16H2,1-3H3/b11-5+
InChIKey DKNQJTQSRPFWBE-VZUCSPMQSA-N
Formula C48H56O26
HBA 26
HBD 13
MW 1048.95
Rotatable Bonds 14
TPSA 402.57
LogP -2.1
Number Rings 8
Number Aromatic Rings 4
Heavy Atom Count 74
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 1048.31
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Astragalus caprinus Leguminosae/Fabaceae Plantae 1042474

Showing of synonyms

  • Semmar N, Fenet B, et al. (2002). New Flavonol Tetraglycosides from Astragalus caprinus. Chemical & pharmaceutical bulletin, 2002, 50(7), 981-4. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)CC(COC(OCC4)CC4OC5CCCCO5)OC2Oc(c6=O)coc(c67)cccc7

Level: 5

Mol. Weight: 706.79 g/mol

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)C(OC5CCCCO5)C(OC(=O)C=Cc6ccccc6)CC4COC(OCC7)CC7OC8CCCCO8

Level: 6

Mol. Weight: 782.88 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(CC2COC3CCCCO3)C(OC4CCCCO4)C(O2)Oc(c5=O)c(-c6ccccc6)oc(c57)cccc7

Level: 5

Mol. Weight: 682.77 g/mol

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(O4)CC(OC(=O)C=Cc5ccccc5)CC4COC(OCC6)CC6OC7CCCCO7

Level: 5

Mol. Weight: 682.77 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OCC3CCC(OC4CCCCO4)C(O3)Oc(c5=O)c(-c6ccccc6)oc(c57)cccc7

Level: 5

Mol. Weight: 636.74 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)CC(COC4CCCCO4)OC2Oc(c5=O)coc(c56)cccc6

Level: 4

Mol. Weight: 606.67 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC(O3)CC(OC(=O)C=Cc4ccccc4)CC3COC(OCC5)CC5OC6CCCCO6

Level: 4

Mol. Weight: 606.67 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(CC2COC3CCCCO3)CC(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 582.65 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)CCOC2Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 568.62 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OCC3CCC(OC4CCCCO4)C(O3)Oc(c5=O)coc(c56)cccc6

Level: 4

Mol. Weight: 560.64 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C(CO2)OC3CCCCO3)CC2COC(OCC4)CC4OC5CCCCO5

Level: 4

Mol. Weight: 546.66 g/mol

Structure

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 536.62 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 536.62 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(CC2COC3CCCCO3)CC(O2)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 506.55 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)CCOC2Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 492.52 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 468.51 g/mol

Structure

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 460.52 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 460.52 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(CCO2)CC2COC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 446.54 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(C(CO2)OC3CCCCO3)CC2COC4CCCCO4

Level: 3

Mol. Weight: 446.54 g/mol

Structure

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

Level: 3

Mol. Weight: 436.5 g/mol

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 422.48 g/mol

Structure

SMILES: O1CCCCC1OC(CO2)CCC2COC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 400.51 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 392.41 g/mol

Structure

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

Level: 2

Mol. Weight: 360.41 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC(CCO2)CC2COC3CCCCO3

Level: 2

Mol. Weight: 346.42 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 346.38 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 332.4 g/mol

Structure

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

Level: 2

Mol. Weight: 322.36 g/mol

Structure

SMILES: O1CCCCC1OCC2CCC(CO2)OC3CCCCO3

Level: 2

Mol. Weight: 300.4 g/mol

Structure

SMILES: O1CCCCC1COC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 300.4 g/mol

Structure

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

Level: 1

Mol. Weight: 246.26 g/mol

Structure

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 232.28 g/mol

Structure

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

Level: 1

Mol. Weight: 222.24 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 200.28 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 186.25 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 186.25 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 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
215764.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
28198799.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.690
Plasma Protein Binding
-17.95
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
6.690
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-655834.940
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.180
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.050
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
-51179458822.440
Rat (Acute)
2.570
Rat (Chronic Oral)
110.680
Fathead Minnow
64603193.120
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
5756262312.420
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-3191.740
Log(P)
0.18
Log S
-5.74
Log(Vapor Pressure)
-189550742.22
Melting Point
235.57
pKa Acid
-1381102.78
pKa Basic
-11098.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9327
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8810
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8669
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8654
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8628
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8059
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7771
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7550
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7509
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7505
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7490
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7476
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7288
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7243
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7229
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7115
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7091
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7040

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