Vanilic acid 4-O-beta-D-6-O-benzoylglucopyranoside - Compound Card

Vanilic acid 4-O-beta-D-6-O-benzoylglucopyranoside

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Vanilic acid 4-O-beta-D-6-O-benzoylglucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glucoside
Canonical Smiles COc1cc(ccc1OC1OC(COC(=O)c2ccccc2)C(C(C1O)O)O)C(=O)O
InChI InChI=1S/C21H22O10/c1-28-14-9-12(19(25)26)7-8-13(14)30-21-18(24)17(23)16(22)15(31-21)10-29-20(27)11-5-3-2-4-6-11/h2-9,15-18,21-24H,10H2,1H3,(H,25,26)
InChIKey PFBCWAXHYYPDIO-UHFFFAOYSA-N
Formula C21H22O10
HBA 9
HBD 4
MW 434.4
Rotatable Bonds 7
TPSA 151.98
LogP 0.44
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 434.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Canthium multiflorum Rubiaceae Plantae 271244

Showing of synonyms

  • Kouam SF, Ngouonpe AW, et al. (2013). Monoterpenes with antibacterial activities from a Cameroonian medicinal plant Canthium Multiflorum (Rubiaceae).. Fitoterapia,2013, 91, 199-204. [View] [PubMed]
Pubchem: 162956014

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 434.4 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 434.4 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 434.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 434.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.26
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.140
Plasma Protein Binding
38.36
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
4.690
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.730
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.240
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
-39.350
Rat (Acute)
2.000
Rat (Chronic Oral)
4.070
Fathead Minnow
4.100
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
468.310
Hydration Free Energy
-4.540
Log(D) at pH=7.4
-0.350
Log(P)
1.58
Log S
-3.16
Log(Vapor Pressure)
-10.18
Melting Point
184.5
pKa Acid
4.72
pKa Basic
2.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9632
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.9090
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8874
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8719
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8443
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8421
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8393
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8325
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8296
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8128
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8058
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8037
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8009
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8009
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8009
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8009
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7993
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7948
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7918
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7901
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7851
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.7846
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7687
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7647
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7598
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7558
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7548
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7509
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7493
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7450
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7445
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7404
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7404
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7384
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7365
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7290
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7282
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7273
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7261
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7245
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7226
Orf1ab polyprotein Q6T1E9 Q6T1E9_CVHSA SARS coronavirus CUHK-L2 3 0.7224
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7210
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7198
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7163
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7149
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7141
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7140
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7104
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7101
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7064
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7056
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7007
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7005
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7002

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