Variabiloside E - Compound Card

Variabiloside E

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Variabiloside E

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles O=C(O[C@H]1C(CO[C@@H]2OC(C)[C@@H]([C@@H](C2O)O)O)O[C@H](C(C1O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O)/C=C/c1ccc(cc1)O
InChI InChI=1S/C36H36O18/c1-14-26(43)28(45)30(47)35(50-14)49-13-23-33(53-24(42)9-4-15-2-6-17(37)7-3-15)29(46)31(48)36(52-23)54-34-27(44)25-21(41)11-18(38)12-22(25)51-32(34)16-5-8-19(39)20(40)10-16/h2-12,14,23,26,28-31,33,35-41,43,45-48H,13H2,1H3/b9-4+/t14?,23?,26-,28-,29?,30?,31?,33-,35+,36-/m0/s1
InChIKey HLWFQXZBFQLASS-SOABGZHQSA-N
Formula C36H36O18
HBA 18
HBD 10
MW 756.67
Rotatable Bonds 9
TPSA 295.73
LogP 0.28
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: 44259128
Nmrshiftdb2: 70038278

No compound-protein relationship available.

Structure

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

Level: 4

Mol. Weight: 756.67 g/mol

Structure

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

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

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

Level: 2

Mol. Weight: 756.67 g/mol

Structure

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

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: 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: O1CCCCC1COC2CCCCO2

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

Inhibitory toward advanced glycation end-products formation

Absorption

Caco-2 (logPapp)
-6.59
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
6.96
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1700.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.83
Plasma Protein Binding
42.5
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
12.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-38.84
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.11
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
-3084541.19
Rat (Acute)
2.41
Rat (Chronic Oral)
4.72
Fathead Minnow
3901.71
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
339463.65
Hydration Free Energy
-2.92
Log(D) at pH=7.4
0.38
Log(P)
2.18
Log S
-5.66
Log(Vapor Pressure)
-11174.14
Melting Point
229.41
pKa Acid
-51.73
pKa Basic
4.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9236
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9236
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8992
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8992
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8856
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8856
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8847
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8847
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8809
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8809
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8792
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8792
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8749
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8749
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8671
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8671
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8631
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8631
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8616
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8616
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8284
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8284
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8239
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8239
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8158
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8158
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8142
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8142
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8013
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8013
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7942
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7942
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7886
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7886
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7843
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7843
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7809
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7809
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7771
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7771
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7759
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7759
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7733
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7733
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7721
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7721
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7673
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7673
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7622
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7622
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7607
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7607
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7588
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7588
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7536
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7536
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7500
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7500
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7494
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7494
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7401
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7401
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7392
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7392
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7390
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7390
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7390
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7390
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7366
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7366
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7327
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7327
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7243
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7243
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7225
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7225
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7205
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7205
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7194
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7194
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7193
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7193
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7179
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7179
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7162
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7162
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7154
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7154
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7144
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7144
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7138
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7138
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7114
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7114
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7105
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7105
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7103
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7103
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7072
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7072
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7050
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7050
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7041
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7041
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7038
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7038
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7015
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7015

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