(2S)-4'-hydroxy-5-methoxy-6'',6''-dimethylpyrano[2'',3'':7,8]flavanone - Compound Card

(2S)-4'-hydroxy-5-methoxy-6'',6''-dimethylpyrano[2'',3'':7,8]flavanone

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(2S)-4'-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[C@H](O2)c1ccc(cc1)O
InChI InChI=1S/C21H20O5/c1-21(2)9-8-14-17(26-21)11-18(24-3)19-15(23)10-16(25-20(14)19)12-4-6-13(22)7-5-12/h4-9,11,16,22H,10H2,1-3H3/t16-/m0/s1
InChIKey FMFCFFOLQZZBDX-INIZCTEOSA-N
Formula C21H20O5
HBA 5
HBD 1
MW 352.39
Rotatable Bonds 2
TPSA 64.99
LogP 4.29
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: 101584233

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)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.670
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.320
Plasma Protein Binding
79.28
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.160
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.480
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.860
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.350
Rat (Acute)
2.560
Rat (Chronic Oral)
1.940
Fathead Minnow
4.830
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
452.760
Hydration Free Energy
-7.510
Log(D) at pH=7.4
3.500
Log(P)
3.63
Log S
-5.74
Log(Vapor Pressure)
-8.07
Melting Point
185.03
pKa Acid
9.0
pKa Basic
4.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9378
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9378
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9015
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9015
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8971
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8971
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8926
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8926
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8890
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8890
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8837
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8837
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8791
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8791
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8683
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8683
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8677
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8677
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8656
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8656
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8586
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8586
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8577
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8577
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8562
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8562
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8351
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8351
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8306
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8306
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8200
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8200
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7962
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7962
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7934
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7934
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7928
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7928
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7898
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7898
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7878
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7878
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7875
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7875
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7858
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7858
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7804
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7804
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7734
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7734
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7717
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7717
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7623
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7623
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7617
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7617
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7600
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7600
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7541
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7541
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7538
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7538
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7534
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7534
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7527
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7527
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7500
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7500
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7440
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7440
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7428
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7428
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7412
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7412
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7396
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7396
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7368
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7368
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7358
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7358
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7345
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7345
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7338
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7338
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7338
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7338
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7329
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7329
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7300
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7300
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7259
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7259
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7258
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7258
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7252
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7252
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7250
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7250
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7229
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7229
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7208
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7208
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7205
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7205
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7203
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7203
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7179
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7179
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7171
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7171
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7169
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7169
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7143
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7143
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7140
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7140
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7131
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7131
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7130
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7130
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7126
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7126
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7119
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7119
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7115
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7115
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7109
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7109
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7083
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7083
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7082
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7082
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7077
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7077
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7074
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7074
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7072
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7072
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7069
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7069
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7060
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7060
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7059
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7059
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7044
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7044
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7038
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7038
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7030
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7030
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7029
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7029
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7021
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7021
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7016
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7016
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7001
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7001

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