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

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

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3-(4-methoxyphenyl)-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(cc1)OC
InChI InChI=1S/C22H20O5/c1-22(2)10-9-15-20-16(11-18(25-4)21(15)27-22)19(23)17(12-26-20)13-5-7-14(24-3)8-6-13/h5-12H,1-4H3
InChIKey QGVRYCDFFNUEAM-UHFFFAOYSA-N
Formula C22H20O5
HBA 5
HBD 0
MW 364.4
Rotatable Bonds 3
TPSA 57.9
LogP 4.66
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 364.13
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
4 Millettia dura Leguminosae/Fabaceae Plantae 62119
5 Millettia ferruginea Leguminosae/Fabaceae Plantae 1096003

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, Midiwo JO, et al. (1997). 6-Methoxycalpogonium Isoflavone A: A New Isoflavone from the Seed Pods of Millettia dura.. Journal of Natural Products,1997,60(8),806–807. [View] [PubMed]
  • Buyinza D, Yang LJ, et al. (2021). Cytotoxicity of isoflavones from Millettia dura. Natural product research, 2021, 35(16), 2744–2747. [View]
  • Buyinza D, Chalo DM, et al. (2020). Flavonoids and Isoflavonoids of Millettia dura and Millettia ferruginea: Phytochemical review and chemotaxonomic values. Biochemical Systematics and Ecology, 2020, 91, 104053. [View]
Pubchem: 1023769
Nmrshiftdb2: 70072635

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 364.4 g/mol

Structure

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

Level: 0

Mol. Weight: 364.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 364.4 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.440
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.460
Plasma Protein Binding
76.31
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.230
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.130
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.020
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.600
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
-3.250
Rat (Acute)
3.430
Rat (Chronic Oral)
1.620
Fathead Minnow
5.420
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
471.720
Hydration Free Energy
-6.820
Log(D) at pH=7.4
3.310
Log(P)
4.42
Log S
-5.51
Log(Vapor Pressure)
-7.76
Melting Point
169.27
pKa Acid
9.2
pKa Basic
3.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9689
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9689
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.9280
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.9280
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9064
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9064
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9029
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9029
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8943
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8943
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8918
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8918
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8463
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8463
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8318
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8318
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8289
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8289
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8285
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8285
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8072
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8072
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7988
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7988
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7942
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7942
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7860
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7860
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7857
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7857
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7848
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7848
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7837
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7837
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7812
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7812
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7767
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7767
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7761
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7761
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7753
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7753
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7742
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7742
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7739
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7739
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7730
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7730
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7713
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7713
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7689
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7689
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7677
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7677
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7672
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7672
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7663
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7663
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7617
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7617
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7574
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7574
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7512
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7512
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7491
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7491
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 2 0.7481
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 2 0.7481
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7473
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7473
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7460
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7460
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7453
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7453
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7413
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7413
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7410
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7410
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7403
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7403
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7384
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7384
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7374
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7374
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7373
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7373
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7345
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7345
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7309
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7309
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7307
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7307
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7306
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7306
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7302
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7302
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7297
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7297
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7293
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7293
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7288
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7288
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7278
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7278
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7275
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7275
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7259
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7259
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7242
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7242
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7242
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7242
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7201
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7201
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7183
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7183
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7145
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7145
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7141
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7141
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7138
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7138
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7135
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7135
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7135
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7135
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7132
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7132
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7107
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7107
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7092
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7092
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7089
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7089
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 2 0.7072
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 2 0.7072
Nucleoside diphosphate kinase Q5HFV4 NDK_STAAC Staphylococcus aureus 2 0.7055
Nucleoside diphosphate kinase Q5HFV4 NDK_STAAC Staphylococcus aureus 2 0.7055
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7052
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7052
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7043
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7043
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7029
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7029
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7028
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7028
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 2 0.7012
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 2 0.7012
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7010
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7010
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7000
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7000

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