(2R,3R)-3-hydroxy-5-methoxy-6'',6''-dimethylpyrano[2'',3'':7,8]flavanone - Compound Card

(2R,3R)-3-hydroxy-5-methoxy-6'',6''-dimethylpyrano[2'',3'':7,8]flavanone

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(2R,3R)-3-hydroxy-5-methoxy-6'',6''-dimethylpyrano[2'',3'':7,8]flavanone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1cc2OC(C)(C)C=Cc2c2c1C(=O)[C@H](O)[C@H](O2)c1ccccc1
InChI InChI=1S/C21H20O5/c1-21(2)10-9-13-14(26-21)11-15(24-3)16-17(22)18(23)19(25-20(13)16)12-7-5-4-6-8-12/h4-11,18-19,23H,1-3H3/t18-,19+/m0/s1
InChIKey RUDILYVZCUZXBH-RBUKOAKNSA-N
Formula C21H20O5
HBA 5
HBD 1
MW 352.39
Rotatable Bonds 2
TPSA 64.99
LogP 3.56
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 352.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia vogelii Leguminosae/Fabaceae Plantae 1157238

Showing of synonyms

  • Stevenson PC, Kite GC, et al. (2012). Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment.. Phytochemistry,2012(78),135-146. [View] [PubMed]
Pubchem: 101584237

No compound-protein relationship available.

Structure

SMILES: C1=CCOc2ccc(c3c12)C(=O)CC(O3)c4ccccc4

Level: 1

Mol. Weight: 352.39 g/mol

Structure

SMILES: O1CCC(=O)c(c1c23)ccc2OCC=C3

Level: 0

Mol. Weight: 352.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 352.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.480
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.360
Plasma Protein Binding
88.04
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.980
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.090
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.270
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.820
Micronucleos
Toxic
NR-AhR
Toxic
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
-1.740
Rat (Acute)
3.120
Rat (Chronic Oral)
1.950
Fathead Minnow
4.700
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
429.170
Hydration Free Energy
-7.690
Log(D) at pH=7.4
3.320
Log(P)
3.61
Log S
-4.54
Log(Vapor Pressure)
-8.1
Melting Point
164.21
pKa Acid
8.46
pKa Basic
2.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9077
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9077
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8803
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8803
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8784
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8784
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8726
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8726
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8665
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8665
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8509
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8509
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8391
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8391
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8386
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8386
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8381
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8381
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8367
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8367
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8335
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8335
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8306
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8306
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8299
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8299
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8290
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8290
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8259
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8259
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8237
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8237
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8231
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8231
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8228
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8228
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8162
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8162
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8144
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8144
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8057
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8057
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8023
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8023
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7962
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7962
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7933
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7933
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7919
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7919
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7859
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7859
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7717
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7717
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7629
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7629
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7541
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7541
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7527
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7527
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7513
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7513
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7504
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7504
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7491
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7491
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7451
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7451
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7430
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7430
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7382
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7382
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7303
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7303
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7299
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7299
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7289
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7289
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7283
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7283
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7241
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7241
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7234
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7234
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7200
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7200
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7178
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7178
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7163
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7163
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7155
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7155
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7147
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7147
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7123
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7123
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7117
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7117
Metallo-beta-lactamase type 2 P25910 BLAB_BACFG Bacteroides fragilis 3 0.7108
Metallo-beta-lactamase type 2 P25910 BLAB_BACFG Bacteroides fragilis 3 0.7108
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7103
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7103
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7024
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7024
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7001
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7001
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7001
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7001

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