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

(2S)-5-methoxy-6'',6''-dimethyl-4'',5''-dihydrocyclopropa[4'',5'']furano[2'',3'':7,8]flavanone

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(2S)-5-methoxy-6'',6''-dimethyl-4'',5''-dihydrocyclopropa[4'',5'']furano[2'',3'':7,8]flavanone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1cc2OC3C(c2c2c1C(=O)C[C@H](O2)c1ccccc1)C3(C)C
InChI InChI=1S/C21H20O4/c1-21(2)18-17-15(25-20(18)21)10-14(23-3)16-12(22)9-13(24-19(16)17)11-7-5-4-6-8-11/h4-8,10,13,18,20H,9H2,1-3H3/t13-,18?,20?/m0/s1
InChIKey NGRRXMZEVSBATO-VUXUOOGWSA-N
Formula C21H20O4
HBA 4
HBD 0
MW 336.39
Rotatable Bonds 2
TPSA 44.76
LogP 4.29
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 336.14
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: 101584234

No compound-protein relationship available.

Structure

SMILES: C12C(C1)Oc3c2c4c(cc3)C(=O)CC(O4)c5ccccc5

Level: 1

Mol. Weight: 336.39 g/mol

Structure

SMILES: C12C(C1)Oc3c2c4c(cc3)C(=O)CCO4

Level: 0

Mol. Weight: 336.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 336.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.0
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.550
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.530
Plasma Protein Binding
84.25
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.290
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.970
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.080
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.710
Micronucleos
Safe
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
-0.930
Rat (Acute)
2.460
Rat (Chronic Oral)
1.850
Fathead Minnow
5.100
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
441.750
Hydration Free Energy
-5.770
Log(D) at pH=7.4
3.410
Log(P)
4.27
Log S
-5.65
Log(Vapor Pressure)
-7.66
Melting Point
147.06
pKa Acid
10.21
pKa Basic
4.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9094
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9094
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9027
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9027
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8876
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8876
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8788
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8788
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8676
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8676
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8633
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8633
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8544
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8544
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8415
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8415
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8266
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8266
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8106
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8106
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7911
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7911
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7881
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7881
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7821
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7821
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7805
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7805
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7707
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7707
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7660
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7660
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7655
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7655
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7621
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7621
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7596
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7596
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7568
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7568
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7517
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7517
Transcriptional enhancer factor TEF-4 Q15562 TEAD2_HUMAN Homo sapiens 3 0.7408
Transcriptional enhancer factor TEF-4 Q15562 TEAD2_HUMAN Homo sapiens 3 0.7408
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 2 0.7407
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 2 0.7407
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7400
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7400
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7354
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7354
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7327
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7327
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7306
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7306
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7242
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7242
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7235
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7235
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7204
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7204
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7202
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7202
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7157
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7157
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7147
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7147
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7124
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7124
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7114
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7114
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7107
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7107
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7076
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7076
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7030
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7030
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7029
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7029

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