Trans-3-hydroxy-5-methoxy-6,7-methylenedioxyflavanone - Compound Card

Trans-3-hydroxy-5-methoxy-6,7-methylenedioxyflavanone

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Trans-3-hydroxy-5-methoxy-6,7-methylenedioxyflavanone

Structure
Zoomed Structure
  • Family: Plantae - Iridaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Dihydroflavonol
Canonical Smiles COc1c2c(O[C@@H]([C@H](C2=O)O)c2ccccc2)cc2c1OCO2
InChI InChI=1S/C17H14O6/c1-20-17-12-10(7-11-16(17)22-8-21-11)23-15(14(19)13(12)18)9-5-3-2-4-6-9/h2-7,14-15,19H,8H2,1H3/t14-,15+/m0/s1
InChIKey MJAIKSJQFBNFDU-LSDHHAIUSA-N
Formula C17H14O6
HBA 6
HBD 1
MW 314.29
Rotatable Bonds 2
TPSA 74.22
LogP 2.1
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 314.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dietes bicolor Iridaceae Plantae 93015

Showing of synonyms

  • Ayoub I.M, Korinek M, et al. (2018). Probing the antiallergic and anti-inflammatory activity of biflavonoids and dihydroflavonols from dietes bicolor. Journal of natural products, 2018, 81(2), 243-253. [View] [PubMed]
Pubchem: 21721856
Chebi: 67372
Nmrshiftdb2: 60060737
Metabolights: MTBLC67372

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c(c2)C(=O)CC(O3)c4ccccc4

Level: 1

Mol. Weight: 314.29 g/mol

Structure

SMILES: O1COc(c12)cc3c(c2)C(=O)CCO3

Level: 0

Mol. Weight: 314.29 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 314.29 g/mol

Anti-inflammatory
Antiallergic

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.400
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.420
Plasma Protein Binding
86.21
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
9.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.760
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.840
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.710
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
0.980
Rat (Acute)
2.240
Rat (Chronic Oral)
1.810
Fathead Minnow
4.570
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
398.240
Hydration Free Energy
-9.030
Log(D) at pH=7.4
2.020
Log(P)
2.37
Log S
-3.71
Log(Vapor Pressure)
-7.8
Melting Point
145.57
pKa Acid
7.49
pKa Basic
0.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9892
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.9404
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9217
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9099
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.9089
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9040
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9023
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8977
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8965
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8952
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8949
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8870
Quercetin 2,3-dioxygenase Q7SIC2 QDOI_ASPJA Aspergillus japonicus 4 0.8855
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8848
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8839
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8829
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8811
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8717
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8685
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8671
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8651
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8613
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8545
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8507
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8506
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8497
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8479
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8436
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8418
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8416
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8411
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8385
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8348
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8344
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8334
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8332
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8331
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8324
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8300
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8283
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8193
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8186
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8186
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8139
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8136
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8079
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8073
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8058
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8014
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7989
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7983
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7973
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7939
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7921
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7883
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7859
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7835
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7828
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7819
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7803
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7798
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7790
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7780
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7777
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7750
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7742
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7734
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7733
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7720
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7718
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7690
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7662
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7631
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7627
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7595
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7594
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7585
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7582
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7552
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 4 0.7529
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7519
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7510
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7484
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7450
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7447
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7437
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7414
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7402
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7378
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7359
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7350
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7346
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7329
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7322
Quercetin 2,3-dioxygenase Q7SIC2 QDOI_ASPJA Aspergillus japonicus 4 0.7292
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7281
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7264
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7260
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7244
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7244
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7240
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7226
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 4 0.7213
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7194
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7167
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7161
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 4 0.7156
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7149
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7144
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 2 0.7143
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7133
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7128
Protein mono-ADP-ribosyltransferase PARP15 Q460N3 PAR15_HUMAN Homo sapiens 3 0.7128
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7121
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7113
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7113
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7112
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7110
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7109
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7107
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7100
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7092
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7092
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7060
Metallo-beta-lactamase type 2 P25910 BLAB_BACFG Bacteroides fragilis 3 0.7051
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7046
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7015
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7003

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