7,7'-dimethoxy-6,6'-biscoumarin - Compound Card

7,7'-dimethoxy-6,6'-biscoumarin

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7,7'-dimethoxy-6,6'-biscoumarin

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Coumarin Derivative
Canonical Smiles COc1cc2oc(=O)ccc2cc1c1cc2ccc(=O)oc2cc1OC
InChI InChI=1S/C20H14O6/c1-23-17-9-15-11(3-5-19(21)25-15)7-13(17)14-8-12-4-6-20(22)26-16(12)10-18(14)24-2/h3-10H,1-2H3
InChIKey IVNWPVRKHOOFTF-UHFFFAOYSA-N
Formula C20H14O6
HBA 6
HBD 0
MW 350.33
Rotatable Bonds 3
TPSA 78.88
LogP 3.58
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.1
Exact Mass 350.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum riparium Guttiferae Plantae 269018

Showing of synonyms

  • Tanemossu SA, Franke K, et al. (2014). Rare biscoumarin derivatives and flavonoids from Hypericum riparium.. Phytochemistry,2014, 105, 171-177. [View] [PubMed]
Pubchem: 86176075

No compound-protein relationship available.

Structure

SMILES: c1cc(=O)oc(c12)ccc(c2)-c(c3)ccc(c34)oc(=O)cc4

Level: 1

Mol. Weight: 350.33 g/mol

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 350.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.690
Plasma Protein Binding
84.03
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
6.100
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
1.690
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.840
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.870
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
-1.220
Rat (Acute)
2.290
Rat (Chronic Oral)
1.330
Fathead Minnow
5.550
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
509.640
Hydration Free Energy
-8.460
Log(D) at pH=7.4
2.810
Log(P)
3.05
Log S
-5.58
Log(Vapor Pressure)
-8.73
Melting Point
278.77
pKa Acid
7.25
pKa Basic
4.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9676
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9645
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.9634
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9352
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.9347
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9263
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9251
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9237
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9230
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9216
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.9207
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9182
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9173
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9139
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9091
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9053
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9016
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.9002
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8969
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8954
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8935
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8890
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8824
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8738
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8732
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8731
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8708
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8700
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8677
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8633
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8627
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8581
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8537
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8535
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8527
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8482
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8457
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8426
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8343
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8320
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8292
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8291
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8267
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8231
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8224
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8170
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8160
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8147
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8142
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8139
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7992
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7972
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7968
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7959
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7931
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7922
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 4 0.7903
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7874
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7867
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7823
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7802
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7780
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7773
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7772
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7730
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7714
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7704
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7687
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7678
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7655
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7638
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7630
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7616
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7613
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7611
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7583
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7582
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7579
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7563
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7555
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.7550
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7532
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7528
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7517
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7505
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7481
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7479
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7474
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7472
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7465
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7461
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7460
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7451
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 4 0.7450
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7448
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7447
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7445
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7440
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7431
Mu-type opioid receptor P42866 OPRM_MOUSE Mus musculus 3 0.7428
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7428
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7418
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7418
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7391
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7383
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7372
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7364
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7361
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7351
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7351
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7350
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7350
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7339
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7320
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7314
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7313
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7313
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 2 0.7307
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7302
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7298
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7276
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7273
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 2 0.7264
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7261
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7254
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7246
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7245
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7245
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7242
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7239
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 2 0.7234
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7228
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7219
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7207
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7194
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7193
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7191
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7187
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7182
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7171
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7163
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7152
CRP-like cAMP-activated global transcriptional regulator P9WMH3 CRPL_MYCTU Mycobacterium tuberculosis 3 0.7149
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7142
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 2 0.7142
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7129
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7126
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7125
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7120
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7109
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7108
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7106
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 4 0.7101
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7096
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7087
Serine/threonine-protein kinase 25 O00506 STK25_HUMAN Homo sapiens 4 0.7081
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7079
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7072
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7068
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7064
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7050
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7047
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7046
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7046
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7037
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7037
Transthyretin P02766 TTHY_HUMAN Homo sapiens 3 0.7011
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7006
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7005
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7002

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