2',6'-dihydroxy-4'-methoxydihydrochalcone - Compound Card

2',6'-dihydroxy-4'-methoxydihydrochalcone

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2',6'-dihydroxy-4'-methoxydihydrochalcone

Structure
Zoomed Structure
  • Family: Plantae - Polygonaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COC1=CC(O)C(C(=C1)O)C(=O)/C=C/c1ccccc1
InChI InChI=1S/C16H16O4/c1-20-12-9-14(18)16(15(19)10-12)13(17)8-7-11-5-3-2-4-6-11/h2-10,14,16,18-19H,1H3/b8-7+
InChIKey JYKQJAUWHLNCIH-BQYQJAHWSA-N
Formula C16H16O4
HBA 4
HBD 2
MW 272.3
Rotatable Bonds 4
TPSA 66.76
LogP 2.23
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 272.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Polygonum senegalense Polygonaceae Plantae 471708

Showing of synonyms

  • Midiwo JO, Matasi JJ, et al. (1992). Anti-feedant effects of surface accumulated flavonoids of Polygonum senegalense.. Bulletin of the Chemical Society of Ethiopia,1992,6(2),119-122. [View] [PubMed]
Pubchem: 169676
Kegg Ligand: C09644
Chebi: 28523
Nmrshiftdb2: 60030993
Bindingdb: 50491174

No compound-protein relationship available.

Structure

SMILES: C1C=CC=CC1C(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 272.3 g/mol

Structure

SMILES: C1=CCCC=C1

Level: 0

Mol. Weight: 272.3 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 272.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.870
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.790
Plasma Protein Binding
21.03
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
4.190
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.490
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.670
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.930
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
3.390
Rat (Acute)
2.660
Rat (Chronic Oral)
2.890
Fathead Minnow
4.300
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
366.700
Hydration Free Energy
-13.110
Log(D) at pH=7.4
1.310
Log(P)
2.24
Log S
-2.77
Log(Vapor Pressure)
-6.82
Melting Point
135.89
pKa Acid
7.6
pKa Basic
2.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9582
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9582
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9168
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9168
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8962
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8962
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8875
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8875
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8807
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8807
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8730
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8730
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8633
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8633
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8347
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8347
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8323
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8323
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7982
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7982
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7956
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7956
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7945
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7945
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.7930
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.7930
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7888
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7888
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7880
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7880
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7821
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7821
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7801
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7801
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7782
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7782
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7767
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7767
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7695
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7695
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7672
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7672
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7619
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7619
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7617
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7617
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7546
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7546
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 2 0.7544
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 2 0.7544
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7541
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7541
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7512
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7512
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7474
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7474
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7442
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7442
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7439
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7439
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7405
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7405
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7400
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7400
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7394
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7394
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7351
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7351
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7345
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7345
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7341
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7341
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7322
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7322
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7299
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7299
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7283
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7283
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7269
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7269
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7260
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7260
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7257
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7257
L-glutamine synthetase Q1QZR8 Q1QZR8_CHRSD Chromohalobacter salexigens 3 0.7245
L-glutamine synthetase Q1QZR8 Q1QZR8_CHRSD Chromohalobacter salexigens 3 0.7245
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7244
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7244
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7238
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7238
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7234
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7234
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7214
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7214
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7207
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7207
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7202
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7202
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7197
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7197
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7192
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7192
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7191
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7191
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7180
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7180
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7179
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7179
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7161
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7161
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7125
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7125
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7122
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7122
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7108
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7108
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7103
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7103
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7103
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7103
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7086
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7086
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7083
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7083
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7079
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7079
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7061
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7061
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7057
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7057
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7045
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7045
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7044
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7044
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7041
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7041
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7040
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7040
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7034
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7034
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7032
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7032
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7029
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7029
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7025
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7025
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7023
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7023

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