6,7-dimethoxy-3′,4′-methylenedioxy-8-(3,3-dimethylallyl) isoflavone - Compound Card

6,7-dimethoxy-3′,4′-methylenedioxy-8-(3,3-dimethylallyl) isoflavone

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6,7-dimethoxy-3′,4′-methylenedioxy-8-(3,3-dimethylallyl) isoflavone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles COc1cc2c(=O)c(coc2c(c1OC)CC=C(C)C)c1ccc2c(c1)OCO2
InChI InChI=1S/C23H22O6/c1-13(2)5-7-15-22-16(10-20(25-3)23(15)26-4)21(24)17(11-27-22)14-6-8-18-19(9-14)29-12-28-18/h5-6,8-11H,7,12H2,1-4H3
InChIKey HHFBAAAPTNLTEW-UHFFFAOYSA-N
Formula C23H22O6
HBA 6
HBD 0
MW 394.42
Rotatable Bonds 5
TPSA 67.13
LogP 4.71
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 ferruginea Leguminosae/Fabaceae Plantae 1096003

Showing of synonyms

  • 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: 172432789

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc(c2)-c(c3=O)coc(c34)cccc4

Level: 1

Mol. Weight: 394.42 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 394.42 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 394.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.94
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.570
Plasma Protein Binding
88.37
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
7.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.930
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.020
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
-25.400
Rat (Acute)
2.520
Rat (Chronic Oral)
1.580
Fathead Minnow
5.950
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
483.970
Hydration Free Energy
-5.310
Log(D) at pH=7.4
3.110
Log(P)
4.75
Log S
-5.44
Log(Vapor Pressure)
-8.22
Melting Point
135.73
pKa Acid
9.13
pKa Basic
2.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9709
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9543
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9486
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9477
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9443
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9420
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9073
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9046
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8939
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8874
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8873
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8807
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8774
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8749
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8695
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8673
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8598
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8572
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8565
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8526
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8492
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8463
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8423
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8327
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8321
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8291
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8264
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8238
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8147
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8139
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8076
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7976
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7969
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7915
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7902
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7885
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7865
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7849
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7838
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7790
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7776
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7747
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7744
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7742
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7728
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7726
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7717
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7712
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7700
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7690
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7659
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7646
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7630
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7605
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7595
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7556
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7548
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7537
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7517
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7517
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7502
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7487
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7463
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7452
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7447
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7438
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7428
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7405
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform O35904 PK3CD_MOUSE Mus musculus 4 0.7399
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7394
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7383
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7376
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7371
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7337
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7334
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7327
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7293
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7283
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7279
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7275
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7269
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7267
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7243
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7238
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7238
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7226
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7223
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7221
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7220
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7204
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7192
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7190
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7183
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7171
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7168
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7160
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7155
Type IV pilus retractation ATPase PilT P24559 PILT_PSEAE Pseudomonas aeruginosa 3 0.7147
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7147
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7137
Phosphoenolpyruvate carboxykinase [GTP] P9WIH3 PCKG_MYCTU Mycobacterium tuberculosis 3 0.7135
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7132
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7130
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7121
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7076
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7065
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 2 0.7059
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7054
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7054
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7050
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7049
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7046
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7027
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7019
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7018
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7010
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7005

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