2,5-dihydroxybenzoic acid-2-O-beta-4C1-glucopyranoside - Compound Card

2,5-dihydroxybenzoic acid-2-O-beta-4C1-glucopyranoside

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2,5-dihydroxybenzoic acid-2-O-beta-4C1-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Rosaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC[C@H]1O[C@@H](Oc2ccc(cc2C(=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C13H16O9/c14-4-8-9(16)10(17)11(18)13(22-8)21-7-2-1-5(15)3-6(7)12(19)20/h1-3,8-11,13-18H,4H2,(H,19,20)/t8-,9-,10+,11-,13-/m1/s1
InChIKey GEZJVEGHJRPQEX-BZNQNGANSA-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 Cotoneaster orbicularis Rosaceae Plantae 1851000

Showing of synonyms

  • El-Mousallamy AM, Hussein SA, et al. (2000). Unusual phenolic glycosides from Cotoneaster orbicularis. Phytochemistry,2000,53(6),699-704. [View] [PubMed]
Pubchem: 49859721
Chebi: 136922
Nmrshiftdb2: 60022765
Metabolights: MTBLC136922

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)
-5.95
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.480
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.560
Plasma Protein Binding
51.58
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
6.140
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.800
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.920
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.260
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
-2.600
Rat (Acute)
1.850
Rat (Chronic Oral)
3.830
Fathead Minnow
3.580
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
484.110
Hydration Free Energy
-16.560
Log(D) at pH=7.4
-2.780
Log(P)
-1.2
Log S
-1.38
Log(Vapor Pressure)
-11.39
Melting Point
174.55
pKa Acid
3.15
pKa Basic
5.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9099
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9099
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8801
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8801
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8673
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8673
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8278
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8278
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8133
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8133
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8114
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8114
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8090
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8090
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 5 0.8078
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 5 0.8078
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8044
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8044
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8021
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8021
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.8014
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.8014
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8001
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8001
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7953
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7953
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7902
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7902
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7878
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7878
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7741
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7741
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7673
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7673
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.7623
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.7623
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7605
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7605
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7544
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7544
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7501
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7501
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7455
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7455
Riboflavin synthase Q58584 RISC_METJA Methanocaldococcus jannaschii 4 0.7437
Riboflavin synthase Q58584 RISC_METJA Methanocaldococcus jannaschii 4 0.7437
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7406
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7406
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7405
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7405
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7380
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7380
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7374
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7374
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7337
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7337
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7295
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7295
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7213
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7213
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7196
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7196
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7194
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7194
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7165
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7165
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7151
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7151
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7150
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7150
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7116
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7116
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7113
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7113
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7108
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7108
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7061
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7061
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7047
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7047
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7029
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7029
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7012
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7012

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