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

7,7'-dihydroxy-6,6'-biscoumarin

Select a section from the left sidebar

7,7'-dihydroxy-6,6'-biscoumarin

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Coumarin Derivative
Canonical Smiles Oc1cc2oc(=O)ccc2cc1c1cc2ccc(=O)oc2cc1O
InChI InChI=1S/C18H10O6/c19-13-7-15-9(1-3-17(21)23-15)5-11(13)12-6-10-2-4-18(22)24-16(10)8-14(12)20/h1-8,19-20H
InChIKey OHYPGJGCEJEXMH-UHFFFAOYSA-N
Formula C18H10O6
HBA 6
HBD 2
MW 322.27
Rotatable Bonds 1
TPSA 100.88
LogP 2.98
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 322.05
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: 12300127
Nmrshiftdb2: 70070433

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 322.27 g/mol

Structure

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

Level: 0

Mol. Weight: 322.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.190
Plasma Protein Binding
88.13
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.710
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
1.300
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.310
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.450
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.570
Rat (Acute)
2.310
Rat (Chronic Oral)
1.900
Fathead Minnow
4.860
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
521.380
Hydration Free Energy
-12.560
Log(D) at pH=7.4
2.670
Log(P)
1.87
Log S
-5.69
Log(Vapor Pressure)
-10.34
Melting Point
394.55
pKa Acid
7.03
pKa Basic
6.11
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 0.9703
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9387
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9358
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.9270
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9193
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.9192
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9127
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9125
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.9117
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.9086
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.9074
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9011
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.9008
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8883
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8808
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8807
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8770
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8759
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8707
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8694
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 3 0.8694
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8672
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8652
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8593
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8585
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8567
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8560
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8518
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8508
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8485
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8409
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8389
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8386
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8369
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8362
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8349
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8304
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8302
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8275
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.8213
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8168
Calmodulin-like domain protein kinase isoenzyme gamma, related F0V9W9 F0V9W9_NEOCL Neospora caninum 3 0.8158
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8154
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8144
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8137
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8007
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7941
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7929
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7925
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7925
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7916
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7896
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 3 0.7865
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 4 0.7819
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7795
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7765
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7753
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7744
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7722
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7684
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7682
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7651
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7634
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7631
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7629
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7624
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7598
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 4 0.7597
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7588
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7571
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7567
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7553
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7530
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7516
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.7513
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7509
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7507
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7497
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7491
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7491
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7474
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7464
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7442
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7442
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7424
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7417
Mu-type opioid receptor P42866 OPRM_MOUSE Mus musculus 3 0.7410
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7388
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7385
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.7343
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7343
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7318
CRP-like cAMP-activated global transcriptional regulator P9WMH3 CRPL_MYCTU Mycobacterium tuberculosis 3 0.7316
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7313
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 2 0.7303
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7301
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7297
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7296
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7295
Farnesyl pyrophosphate synthase P14324 FPPS_HUMAN Homo sapiens 2 0.7294
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7288
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7288
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7284
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7278
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7273
Cytosolic IMP-GMP specific 5'-nucleotidase Q5ZZB6 Q5ZZB6_LEGPH Legionella pneumophila subsp. pneumophila 3 0.7264
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7251
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7251
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7250
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7241
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7238
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7219
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7213
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7202
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7179
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7179
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7175
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7172
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7159
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7159
Farnesyl pyrophosphate synthase Q86C09 Q86C09_9TRYP Trypanosoma brucei 2 0.7156
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7154
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7137
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 2 0.7135
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7117
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7114
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7105
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7093
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7087
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7085
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7083
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7082
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7077
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7075
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7062
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7055
Uncharacterized protein Q46E79 Q46E79_METBF Methanosarcina barkeri 3 0.7051
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7050
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7047
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7044
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7023
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7019
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7018

Download SDF