3,4-dimethoxyphenyl alpha-D-ribofuranoside - Compound Card

3,4-dimethoxyphenyl alpha-D-ribofuranoside

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3,4-dimethoxyphenyl alpha-D-ribofuranoside

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Furan
Canonical Smiles OC[C@H]1O[C@@H]([C@@H]([C@@H]1O)O)Oc1ccc(c(c1)OC)OC
InChI InChI=1S/C13H18O7/c1-17-8-4-3-7(5-9(8)18-2)19-13-12(16)11(15)10(6-14)20-13/h3-5,10-16H,6H2,1-2H3/t10-,11-,12-,13+/m1/s1
InChIKey OZHRNJRMDDEEBR-LPWJVIDDSA-N
Formula C13H18O7
HBA 7
HBD 3
MW 286.28
Rotatable Bonds 5
TPSA 97.61
LogP -0.48
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 286.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus amstelodami Trichocomaceae Fungi 5054

Showing of synonyms

  • Elsbaey M, Sallam A, et al. (2019). Melanogenesis Inhibitors from the Endophytic Fungus Aspergillus amstelodami. Chem Biodivers,2019,16(8),e1900237. [View] [PubMed]
Pubchem: 146682839
Nmrshiftdb2: 70106986

No compound-protein relationship available.

Structure

SMILES: O1CCCC1Oc2ccccc2

Level: 1

Mol. Weight: 286.28 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 286.28 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 286.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.1
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.370
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.640
Plasma Protein Binding
45.76
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
3.040
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.290
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.240
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.850
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
-0.500
Rat (Acute)
2.060
Rat (Chronic Oral)
2.820
Fathead Minnow
3.790
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
358.670
Hydration Free Energy
-15.230
Log(D) at pH=7.4
0.060
Log(P)
-0.42
Log S
-1.49
Log(Vapor Pressure)
-7.39
Melting Point
146.64
pKa Acid
8.61
pKa Basic
0.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9318
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.9309
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9282
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8984
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8865
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8864
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8714
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8696
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8661
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8530
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8518
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8384
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8311
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8285
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.8193
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8180
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8106
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.8091
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8064
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7962
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7951
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7930
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7911
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7878
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7855
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7821
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7760
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7729
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7703
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7663
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7634
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7633
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7619
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7581
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7554
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7506
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7501
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7490
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7470
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7451
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7441
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7426
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7415
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7412
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7408
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7398
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 4 0.7369
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7357
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7349
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7347
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7301
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7289
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7287
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7287
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7270
cAMP-dependent protein kinase regulatory subunit P07278 KAPR_YEAST Saccharomyces cerevisiae 4 0.7237
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7233
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7221
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7212
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7207
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.7199
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7199
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7195
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7191
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7181
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.7177
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7173
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7157
Alpha-L-fucosidase, putative Q9WYE2 Q9WYE2_THEMA Thermotoga maritima 3 0.7140
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7132
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7129
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7119
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7107
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7105
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7103
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7102
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7102
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7100
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7099
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7090
Thymidylate synthase P13100 TYSY_PNECA Pneumocystis carinii 4 0.7069
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7061
Polyamine aminopropyltransferase Q5SK28 SPEE_THET8 Thermus thermophilus 3 0.7042
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7036
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7032
Spermidine synthase P19623 SPEE_HUMAN Homo sapiens 4 0.7022
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7011
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7009

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