7-hydroxy-5,6-dimethoxy-3′,4′-methylenedioxisoflavone - Compound Card

7-hydroxy-5,6-dimethoxy-3′,4′-methylenedioxisoflavone

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7-hydroxy-5,6-dimethoxy-3′,4′-methylenedioxisoflavone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles COC1C(OC)C(=Cc2c1c(=O)c(co2)c1ccc2c(c1)OCO2)O
InChI InChI=1S/C18H16O7/c1-21-17-11(19)6-14-15(18(17)22-2)16(20)10(7-23-14)9-3-4-12-13(5-9)25-8-24-12/h3-7,17-19H,8H2,1-2H3
InChIKey XBHVGLOOIWEPAT-UHFFFAOYSA-N
Formula C18H16O7
HBA 7
HBD 1
MW 344.32
Rotatable Bonds 3
TPSA 87.36
LogP 2.65
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 344.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 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]

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc(c2)-c(c3=O)coc(c34)C=CCC4

Level: 1

Mol. Weight: 344.32 g/mol

Structure

SMILES: C1CC=Cc(c12)occc2=O

Level: 0

Mol. Weight: 344.32 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 344.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.320
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
31.11
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
7.250
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.510
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.910
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.050
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
-0.730
Rat (Acute)
2.910
Rat (Chronic Oral)
1.780
Fathead Minnow
4.670
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
429.020
Hydration Free Energy
-8.570
Log(D) at pH=7.4
1.630
Log(P)
2.09
Log S
-2.63
Log(Vapor Pressure)
-8.18
Melting Point
182.22
pKa Acid
8.08
pKa Basic
1.55
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 0.9517
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9481
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9397
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9386
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9319
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9247
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.9240
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9214
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9199
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9197
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9143
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9081
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9031
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9022
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9008
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9006
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8983
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8974
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8927
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8918
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8822
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.8787
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8771
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8717
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8689
Cyclic nucleotide-binding domain-containing protein E0RR11 E0RR11_SPITD Spirochaeta thermophila 3 0.8647
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.8604
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8585
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8562
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8539
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.8518
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8500
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8387
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8351
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.8318
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8317
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8278
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8177
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8150
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8024
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.8008
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7989
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7945
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7922
(RS)-norcoclaurine 6-O-methyltransferase Q5C9L7 6OMT_THLFG Thalictrum flavum subsp. glaucum 3 0.7919
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7904
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7903
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7874
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7868
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7853
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7799
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7774
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7756
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7748
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7700
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7687
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7681
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7678
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7675
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7633
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7625
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7612
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7596
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7573
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7546
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7546
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7545
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7544
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7535
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7484
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7476
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7470
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7464
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7461
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7451
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7449
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7421
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7417
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7406
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7400
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7400
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7387
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7378
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7350
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7346
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7342
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7332
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7320
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7318
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7314
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7300
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7299
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7290
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7287
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7278
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7275
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7274
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7270
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7259
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7258
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7251
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7241
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7235
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 1 O88704 HCN1_MOUSE Mus musculus 3 0.7228
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7227
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7220
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7211
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7210
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7209
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7207
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7206
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7205
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7202
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7200
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7183
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7177
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7177
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7172
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 3 0.7155
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7153
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7147
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7147
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7147
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7135
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7131
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7130
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7129
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7113
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7100
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7098
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7093
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7093
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7079
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7074
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7073
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7070
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7055
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 2 0.7054
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 Q9UL51 HCN2_HUMAN Homo sapiens 3 0.7050
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7047
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7040
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7033
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7017
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7016
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7013
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7011
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7010
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7009
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7007
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7005
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7001

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