3,5-dihydroxybenzoic acid-O-glucose - Compound Card

3,5-dihydroxybenzoic acid-O-glucose

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3,5-dihydroxybenzoic acid-O-glucose

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles O=C[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c1cc(O)cc(c1)O)O)O)O)O
InChI InChI=1S/C13H16O9/c14-4-9(17)11(19)12(20)10(18)5-22-13(21)6-1-7(15)3-8(16)2-6/h1-4,9-12,15-20H,5H2/t9-,10+,11+,12+/m0/s1
InChIKey JVCDAHOIIUJTFY-IRCOFANPSA-N
Formula C13H16O9
HBA 9
HBD 6
MW 316.26
Rotatable Bonds 7
TPSA 164.75
LogP -2.1
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.38
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: c1ccccc1

Level: 0

Mol. Weight: 316.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.21
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
33.69
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
10.54
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.62
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.1
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.61
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
-1.37
Rat (Acute)
1.92
Rat (Chronic Oral)
3.44
Fathead Minnow
4.04
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
471.01
Hydration Free Energy
-15.82
Log(D) at pH=7.4
-0.85
Log(P)
-1.4
Log S
-1.78
Log(Vapor Pressure)
-10.67
Melting Point
154.3
pKa Acid
4.84
pKa Basic
5.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9271
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9249
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9158
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9086
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9072
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9064
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9006
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8978
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8968
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8873
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8869
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8842
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8819
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8771
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8762
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8711
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8696
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8613
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8588
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8544
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8517
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8508
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8466
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8459
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8453
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8434
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.8369
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8358
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8331
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8316
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8316
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8255
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8227
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8210
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.8200
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.8166
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8159
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8154
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8131
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8102
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8055
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8055
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8009
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7965
Bifunctional adenosylcobalamin biosynthesis protein CobU Q05599 COBU_SALTY Salmonella typhimurium 4 0.7876
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7873
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7866
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7852
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7840
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7810
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7803
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7724
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7722
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7719
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7651
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7648
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7604
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7579
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7572
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7561
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7549
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7536
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7533
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7529
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7518
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7516
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7470
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7446
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7440
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7437
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7435
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7415
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7396
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7373
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7350
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7345
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7341
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7339
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 4 0.7332
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7311
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7306
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7293
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7259
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7249
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7230
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7214
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7170
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7166
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7163
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7163
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7157
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7126
Histone acetyltransferase KAT2A Q92830 KAT2A_HUMAN Homo sapiens 4 0.7104
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7100
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7098
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7097
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7087
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7067
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7067
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7063
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7063
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7057
Malate dehydrogenase P10584 MDH_THETH Thermus thermophilus 3 0.7056
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7051
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7049
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7047
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7041
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7033
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7030
Ras-related protein M-Ras O08989 RASM_MOUSE Mus musculus 4 0.7020
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7014
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7005
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7002
Rac-like GTP-binding protein ARAC7 O82480 RAC7_ARATH Arabidopsis thaliana 3 0.7001
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7000

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