Kaempferol 3-O-alpha-L-rhamnopyranosyl-(1→6)-(4''-trans-p-coumaroyl) beta-D-galactopyranoside 7-O-alpha-L-rhamnopyranoside - Compound Card

Kaempferol 3-O-alpha-L-rhamnopyranosyl-(1→6)-(4''-trans-p-coumaroyl) beta-D-galactopyranoside 7-O-alpha-L-rhamnopyranoside

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Kaempferol 3-O-alpha-L-rhamnopyranosyl-(1→6)-(4''-trans-p-coumaroyl) beta-D-galactopyranoside 7-O-alpha-L-rhamnopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O[C@H]2O[C@H](CO)[C@@H]([C@H]([C@H]2O)O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@H]1OC(=O)/C=C/c1ccc(cc1)O)O)O
InChI InChI=1S/C36H36O18/c37-13-22-26(43)28(45)30(47)35(51-22)49-19-11-20(41)25-21(12-19)50-32(16-4-8-18(40)9-5-16)34(27(25)44)54-36-31(48)29(46)33(23(14-38)52-36)53-24(42)10-3-15-1-6-17(39)7-2-15/h1-12,22-23,26,28-31,33,35-41,43,45-48H,13-14H2/b10-3+/t22-,23-,26+,28-,29-,30-,31-,33+,35+,36+/m1/s1
InChIKey HGLREUPKZAGYGB-JGXXWBBDSA-N
Formula C36H36O18
HBA 18
HBD 10
MW 756.67
Rotatable Bonds 10
TPSA 295.73
LogP -0.8
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 54
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 756.19
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Ixora undulata Rubiaceae Plantae 1231253

Showing of synonyms

  • Sugimoto S, Wanas AS, et al. (2014). Structure elucidation of secondary metabolites isolated from the leaves of Ixora undulate and their inhibitory activity toward advanced glycation end-products formation. Phytochemistry,2014,108,189-195. [View] [PubMed]
Pubchem: 162817099
Nmrshiftdb2: 70038285

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cc(cc5)OC6CCCCO6

Level: 4

Mol. Weight: 756.67 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)Oc(c3=O)coc(c34)cc(cc4)OC5CCCCO5

Level: 3

Mol. Weight: 756.67 g/mol

Structure

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

Level: 3

Mol. Weight: 756.67 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5

Level: 3

Mol. Weight: 756.67 g/mol

Structure

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

Level: 2

Mol. Weight: 756.67 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4

Level: 2

Mol. Weight: 756.67 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 756.67 g/mol

Structure

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

Level: 2

Mol. Weight: 756.67 g/mol

Structure

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

Level: 1

Mol. Weight: 756.67 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 756.67 g/mol

Structure

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 756.67 g/mol

Structure

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

Level: 1

Mol. Weight: 756.67 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 756.67 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 756.67 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 756.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.61
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
9.820
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
2068.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.810
Plasma Protein Binding
73.79
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
7.150
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-48.680
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.880
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.880
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
-3751219.780
Rat (Acute)
2.570
Rat (Chronic Oral)
4.580
Fathead Minnow
4742.600
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
414952.120
Hydration Free Energy
-2.920
Log(D) at pH=7.4
0.690
Log(P)
0.81
Log S
-4.72
Log(Vapor Pressure)
-13626.71
Melting Point
238.13
pKa Acid
-62.69
pKa Basic
5.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8717
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8717
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8656
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8656
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8618
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8618
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8491
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8491
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8459
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8459
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8297
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8297
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8142
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8142
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7937
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7937
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7884
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7884
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7868
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7868
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7830
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7830
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7814
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7814
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7716
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7716
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7660
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7660
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7636
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7636
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7598
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7598
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7545
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7545
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 4 0.7473
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 4 0.7473
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.7423
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.7423
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7413
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7413
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7396
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7396
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7385
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7385
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7369
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7369
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7368
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7368
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7349
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7349
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7320
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7320
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7300
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7300
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7257
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7257
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7236
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7236
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7205
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7205
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7187
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7187
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7181
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7181
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7158
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7158
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7150
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7150
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7147
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7147
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7135
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7135
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7057
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7057
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7049
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7049
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7047
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7047
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007

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