Vanilloside - Compound Card

Vanilloside

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Vanilloside

Structure
Zoomed Structure
  • Family: Plantae - Acanthaceae
  • Kingdom: Plantae
  • Class: Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2ccc(cc2OC)C=O)[C@@H]([C@H]([C@@H]1O)O)O.COc1cc(C=O)ccc1O
InChI InChI=1S/C14H18O8.C8H8O3/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14;1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10-14,16-19H,6H2,1H3;2-5,10H,1H3/t10-,11-,12+,13-,14-;/m1./s1
InChIKey NQWSTOJMPNBTIR-ABJJILNISA-N
Formula C22H26O11
HBA 11
HBD 5
MW 466.44
Rotatable Bonds 7
TPSA 172.21
LogP -0.1
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 466.15
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ruellia patula Acanthaceae Plantae 441006

Showing of synonyms

  • Samy MN, Khalil HE, et al. (2011). Three new flavonoid glycosides, byzantionoside B 6’-O-Sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula. Chemical and Pharmaceutical Bulletin,2011,59(6),725-729. [View] [PubMed]
Pubchem: 71752919

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 466.44 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 466.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 466.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.550
Plasma Protein Binding
49.79
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
4.800
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.670
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.480
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.100
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
-1.040
Rat (Acute)
1.980
Rat (Chronic Oral)
2.890
Fathead Minnow
3.700
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
420.730
Hydration Free Energy
-17.310
Log(D) at pH=7.4
-0.320
Log(P)
-1.35
Log S
-1.49
Log(Vapor Pressure)
-10.37
Melting Point
164.59
pKa Acid
6.53
pKa Basic
3.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8593
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8593
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8551
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8551
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8501
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8501
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8454
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8454
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8183
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8183
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8171
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8171
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8012
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8012
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8004
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8004
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7987
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7987
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7913
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7913
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7858
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7858
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7842
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7842
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7832
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7832
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7826
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7826
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7786
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7786
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7668
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7668
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7638
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7638
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7549
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7549
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7510
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7510
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7491
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7491
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7461
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7461
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7458
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7458
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7421
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7421
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7394
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7394
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7392
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7392
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7371
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7371
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7359
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7359
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7296
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7296
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7293
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7293
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7290
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7290
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7220
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7220
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7198
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7198
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7197
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7197
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7194
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7194
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7165
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7165
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7159
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7159
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7154
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7154
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7150
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7150
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7137
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7137
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7113
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7113
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7104
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7104
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7078
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7078
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7071
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7071
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7070
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7070
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 4 0.7040
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 4 0.7040
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7039
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7039
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7026
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7026
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7003
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7003
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7000
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7000

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