2-hydroxy-3-O-beta-glucopyranosyl-benzoic acid - Compound Card

2-hydroxy-3-O-beta-glucopyranosyl-benzoic acid

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2-hydroxy-3-O-beta-glucopyranosyl-benzoic acid

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles O1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1Oc1cccc(C(O)=O)c1O
InChI InChI=1S/C13H16O9/c14-4-7-9(16)10(17)11(18)13(22-7)21-6-3-1-2-5(8(6)15)12(19)20/h1-3,7,9-11,13-18H,4H2,(H,19,20)/t7-,9-,10+,11-,13-/m1/s1
InChIKey KVRUHZSAKSIVTD-JEUROIALSA-N
Formula C13H16O9
HBA 8
HBD 6
MW 316.26
Rotatable Bonds 4
TPSA 156.91
LogP -1.73
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 316.08
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Strychnos cocculoides Loganiaceae Plantae 1040870

Showing of synonyms

  • Sunghwa F, Koketsu M. (2009). Phenolic and bis-iridoid glycosides from Strychnos cocculoides.. Natural Product Research,2009,23(15),1408-4015. [View] [PubMed]
Pubchem: 10064327
Chebi: 137992
Nmrshiftdb2: 60059480

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 316.26 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 316.26 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 316.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.79
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.420
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.540
Plasma Protein Binding
56.42
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
5.170
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.590
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.140
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.360
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
-2.480
Rat (Acute)
1.800
Rat (Chronic Oral)
4.000
Fathead Minnow
3.530
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
465.370
Hydration Free Energy
-16.700
Log(D) at pH=7.4
-2.900
Log(P)
-0.07
Log S
-1.58
Log(Vapor Pressure)
-11.66
Melting Point
186.96
pKa Acid
2.79
pKa Basic
5.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9409
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9409
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8820
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8820
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8445
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8445
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8421
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8421
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8237
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8237
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8044
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8044
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7954
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7954
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7914
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7914
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7829
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7829
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7788
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7788
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7649
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7649
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7475
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7475
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7439
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7439
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7400
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7400
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7378
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7378
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7345
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7345
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7323
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7323
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7282
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7282
4-substituted benzoates-glutamate ligase GH3.12 Q9LYU4 GH312_ARATH Arabidopsis thaliana 3 0.7072
4-substituted benzoates-glutamate ligase GH3.12 Q9LYU4 GH312_ARATH Arabidopsis thaliana 3 0.7072
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7064
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7064
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7053
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7053
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7033
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7033

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