4-methoxy-2-O-alpha-D-glucopyranosylphenylmethanol - Compound Card

4-methoxy-2-O-alpha-D-glucopyranosylphenylmethanol

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4-methoxy-2-O-alpha-D-glucopyranosylphenylmethanol

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC[C@@H]1O[C@@H](Oc2cc(OC)ccc2CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C14H20O8/c1-20-8-3-2-7(5-15)9(4-8)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-4,10-19H,5-6H2,1H3/t10-,11-,12+,13-,14+/m0/s1
InChIKey XZJNAGUADSDPHE-PDWCTOEPSA-N
Formula C14H20O8
HBA 8
HBD 5
MW 316.31
Rotatable Bonds 5
TPSA 128.84
LogP -1.63
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 316.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Boswellia dalzielii Burseraceae Plantae 2303552

Showing of synonyms

  • Tegasne C, Kapche GDWF, et al. (2021). Bioguided chemical study of Boswellia dalzielii Hutch. (Burseraceae) for antibacterial agents and a new glucopyranoxylmethoxybenzyle.. Natural product research,2021, 35(23), 5199-5208. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 316.31 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 316.31 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 316.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.37
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.620
Plasma Protein Binding
53.04
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
4.870
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.740
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.120
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.120
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
-1.710
Rat (Acute)
2.010
Rat (Chronic Oral)
3.510
Fathead Minnow
3.310
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
430.060
Hydration Free Energy
-17.690
Log(D) at pH=7.4
-0.680
Log(P)
-1.3
Log S
-1.43
Log(Vapor Pressure)
-10.36
Melting Point
149.94
pKa Acid
6.9
pKa Basic
3.72
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 0.8985
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8890
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8866
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8483
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8220
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8170
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8151
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8134
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8069
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7962
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7951
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7827
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7730
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7720
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7693
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.7692
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7638
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7605
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7567
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7542
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7509
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7493
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7433
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7428
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 4 0.7424
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7404
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7392
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7389
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7327
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7313
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7304
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7275
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7266
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7263
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7237
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7227
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7152
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7146
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7136
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7130
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7115
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7094
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7070
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 3 0.7066
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7065
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7056
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7049
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7046
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7022
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7009

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