5-O-beta-D-glucopyranosyl-2-hydroxyphenylacetic acid - Compound Card

5-O-beta-D-glucopyranosyl-2-hydroxyphenylacetic acid

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5-O-beta-D-glucopyranosyl-2-hydroxyphenylacetic acid

Structure
Zoomed Structure
  • Family: Plantae - Mimosaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Terpenoid Glycoside
Canonical Smiles OCC1OC(Oc2ccc(c(c2)CC(=O)O)O)C(C(C1O)O)O
InChI InChI=1S/C14H18O9/c15-5-9-11(19)12(20)13(21)14(23-9)22-7-1-2-8(16)6(3-7)4-10(17)18/h1-3,9,11-16,19-21H,4-5H2,(H,17,18)
InChIKey CVBZJAYMCXYPNT-UHFFFAOYSA-N
Formula C14H18O9
HBA 8
HBD 6
MW 330.29
Rotatable Bonds 5
TPSA 156.91
LogP -1.8
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 330.1
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Entada rheedei Leguminosae/Fabaceae Plantae 204974
2 Entada rheedei Mimosaceae Plantae 204974

Showing of synonyms

  • Nzowa LK, Teponno RB, et al. (2013). Two new tryptophan derivatives from the seed kernels of Entada rheedei: effects on cell viability and HIV infectivity.. Fitoterapia,2013, 87, 37-42. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 330.29 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 330.29 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 330.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.0
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.44
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
-8.0
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
6.37
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.87
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.77
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.64
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
0.76
Rat (Acute)
1.77
Rat (Chronic Oral)
3.58
Fathead Minnow
3.71
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
468.92
Hydration Free Energy
-15.24
Log(D) at pH=7.4
-3.01
Log(P)
-1.43
Log S
-1.35
Log(Vapor Pressure)
-10.58
Melting Point
162.63
pKa Acid
3.48
pKa Basic
5.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8858
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8846
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8754
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8733
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8692
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8505
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8458
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8400
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8320
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8256
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8238
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7996
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7916
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7914
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7860
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7835
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7769
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7754
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7750
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7670
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7658
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7653
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7632
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7601
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7578
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7561
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7504
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7465
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7415
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7367
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7366
Strictosidine-O-beta-D-glucosidase Q8GU20 SG1_RAUSE Rauvolfia serpentina 5 0.7340
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7339
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7333
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7317
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7307
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7297
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7239
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7223
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7215
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7211
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7208
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7203
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7184
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7106
Alpha-aminoadipic semialdehyde dehydrogenase P49419 AL7A1_HUMAN Homo sapiens 3 0.7096
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7050
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7049
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7045
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7031
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7026
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.7026
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7025
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7021
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7013
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7012

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