3,4-dihydroxybenzoyl-glucoside - Compound Card

3,4-dihydroxybenzoyl-glucoside

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3,4-dihydroxybenzoyl-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC[C@H]1OC(OC(=O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C13H16O9/c14-4-8-9(17)10(18)11(19)13(21-8)22-12(20)5-1-2-6(15)7(16)3-5/h1-3,8-11,13-19H,4H2/t8-,9-,10+,11-,13?/m1/s1
InChIKey MOBYACALHPXMHU-TWEVDUBQSA-N
Formula C13H16O9
HBA 9
HBD 6
MW 316.26
Rotatable Bonds 3
TPSA 156.91
LogP -1.95
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 Rosmarinuseriocalyx Lamiaceae Plantae —

Showing of synonyms

  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CCCCO2

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
Absorbed
Madin-Darby Canine Kidney
-5.28
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
48.37
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
10.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.24
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.86
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.98
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
-0.57
Rat (Acute)
1.82
Rat (Chronic Oral)
3.48
Fathead Minnow
3.67
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
459.97
Hydration Free Energy
-15.18
Log(D) at pH=7.4
-1.15
Log(P)
-1.04
Log S
-1.77
Log(Vapor Pressure)
-10.98
Melting Point
170.48
pKa Acid
4.74
pKa Basic
5.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9069
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8985
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8803
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8797
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8605
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8579
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8548
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8544
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8416
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8410
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8360
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8348
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8307
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8301
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8287
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8240
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8215
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8208
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8128
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8050
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8035
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7897
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7867
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7846
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7794
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7790
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7752
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7629
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7627
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7514
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7503
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7452
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7379
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7338
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7292
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7286
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7271
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7258
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7250
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7238
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7231
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7230
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7228
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7221
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7220
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7178
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7173
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7156
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7138
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7129
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7114
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7113
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7103
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7101
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7096
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7078
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7075
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7062
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7012
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7005

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