3-(3,4-dimethoxyphenyl)-6-methoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one - Compound Card

3-(3,4-dimethoxyphenyl)-6-methoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one

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3-(3,4-dimethoxyphenyl)-6-methoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles COc1cc2c(=O)c(coc2c2c1OC(C)(C)C=C2)c1ccc(c(c1)OC)OC
InChI InChI=1S/C23H22O6/c1-23(2)9-8-14-21-15(11-19(27-5)22(14)29-23)20(24)16(12-28-21)13-6-7-17(25-3)18(10-13)26-4/h6-12H,1-5H3
InChIKey VMYJORXFBILIJU-UHFFFAOYSA-N
Formula C23H22O6
HBA 6
HBD 0
MW 394.42
Rotatable Bonds 4
TPSA 67.13
LogP 4.67
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 394.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia dura Leguminosae/Fabaceae Plantae 62119
2 Millettia dura Leguminosae/Fabaceae Plantae 62119
3 Millettia dura Leguminosae/Fabaceae Plantae 62119

Showing of synonyms

  • Derese S, Barasa L, et al. (2014). 4'-Prenyloxyderrone from the stem bark of Millettia oblata ssp. teitensis and the antiplasmodial activities of isoflavones from some Millettia species.. Phytochemistry Letters,2014,31(8),69-72. [View] [PubMed]
  • Yenesew A, Derese S, et al. (2003). Effect of rotenoids from the seeds of Millettia dura on larvae of Aedes aegypti.. Pest Management Science,2003,59(10),1159-1161. [View] [PubMed]
  • Yenesew A, Midiwo JO, et al. (1996). Four isoflavones from seed pods of Millettia dura. Phytochemistry,1996,41(3),951-955. [View] [PubMed]
Pubchem: 1023565
Nmrshiftdb2: 70035641

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(cc2)c1c(c23)occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 394.42 g/mol

Structure

SMILES: O=c1ccoc(c12)c3c(cc2)OCC=C3

Level: 0

Mol. Weight: 394.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 394.42 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.600
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.430
Plasma Protein Binding
75.31
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.360
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.200
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.980
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.880
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
-15.740
Rat (Acute)
3.740
Rat (Chronic Oral)
1.510
Fathead Minnow
5.560
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
484.540
Hydration Free Energy
-6.150
Log(D) at pH=7.4
2.840
Log(P)
3.96
Log S
-4.8
Log(Vapor Pressure)
-7.72
Melting Point
170.99
pKa Acid
9.13
pKa Basic
2.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9496
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9496
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9487
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9487
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9475
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9475
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9462
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9462
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9286
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9286
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9274
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9274
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9193
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9193
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9010
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9010
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8869
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8869
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8827
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8827
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8658
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8658
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8646
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8646
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8360
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8360
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8287
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8287
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8273
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8273
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8158
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8158
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8090
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8090
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8036
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8036
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8010
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8010
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7896
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7896
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7876
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7876
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7863
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7863
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7782
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7782
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7760
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7760
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7725
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7725
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7709
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7709
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7687
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7687
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7644
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7644
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7622
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7622
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7588
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7588
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7562
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7562
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7549
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7549
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7538
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7538
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7529
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7529
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7520
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7520
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7517
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7517
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7501
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7501
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7486
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7486
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7452
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7452
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7447
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7447
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7440
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7440
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7436
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7436
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7421
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7421
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7418
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7418
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7387
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7387
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7372
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7372
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7363
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7363
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7361
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7361
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7358
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7358
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7346
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7346
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7326
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7326
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7318
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7318
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7310
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7310
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7274
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7274
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7268
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7268
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7250
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7250
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7246
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7246
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7234
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7234
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7228
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7228
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7227
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7227
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7208
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7208
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7200
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7200
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7199
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7199
Phosphoenolpyruvate carboxykinase [GTP] P9WIH3 PCKG_MYCTU Mycobacterium tuberculosis 3 0.7194
Phosphoenolpyruvate carboxykinase [GTP] P9WIH3 PCKG_MYCTU Mycobacterium tuberculosis 3 0.7194
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7179
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7179
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7142
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7142
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 2 0.7139
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 2 0.7139
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7129
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7129
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7121
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7121
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7111
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7111
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7109
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7109
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7108
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7108
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7107
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7107
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7086
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7086
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7086
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7086
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7072
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7072
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7059
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7059
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7040
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7040
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7025
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7025
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7022
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7022
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7011
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7011
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7008
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7008

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