5,7-dimethoxy-6-hydroxycoumarin - Compound Card

5,7-dimethoxy-6-hydroxycoumarin

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5,7-dimethoxy-6-hydroxycoumarin

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles COc1cc2oc(=O)ccc2c(c1O)OC
InChI InChI=1S/C11H10O5/c1-14-8-5-7-6(3-4-9(12)16-7)11(15-2)10(8)13/h3-5,13H,1-2H3
InChIKey PBPNOAHYDPHKFH-UHFFFAOYSA-N
Formula C11H10O5
HBA 5
HBD 1
MW 222.2
Rotatable Bonds 2
TPSA 68.9
LogP 1.52
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 222.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma congoënse Meliaceae Plantae 2590899
2 Entandrophragma congoense Meliaceae Plantae 2590899

Showing of synonyms

  • Happi GM, Kouam SF, et al. (2015). Minor secondary metabolites from the bark of Entandrophragma congoënse (Meliaceae).. Fitoterapia,2015, 102, 35-40. [View] [PubMed]
Pubchem: 3047739
Nmrshiftdb2: 60028857

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 222.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.43
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.160
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.990
Plasma Protein Binding
50.65
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.200
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.510
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.430
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.420
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
3.510
Rat (Acute)
2.070
Rat (Chronic Oral)
2.150
Fathead Minnow
4.130
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
354.390
Hydration Free Energy
-9.600
Log(D) at pH=7.4
0.910
Log(P)
0.71
Log S
-2.66
Log(Vapor Pressure)
-4.92
Melting Point
166.42
pKa Acid
6.57
pKa Basic
3.71
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 0.9880
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9600
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9571
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9551
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9463
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9460
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9159
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.9128
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.9094
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9058
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9036
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.9010
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8997
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8978
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.8973
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8958
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8926
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8850
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8841
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8841
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8807
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8802
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8783
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8781
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8694
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8663
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 4 0.8648
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8644
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8619
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8616
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8604
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8562
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8510
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8478
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8458
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8440
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8404
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8371
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8331
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8308
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8284
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8243
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8219
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8219
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8098
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 3 0.8073
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 3 0.8041
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8035
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7985
Protein mono-ADP-ribosyltransferase PARP10 Q53GL7 PAR10_HUMAN Homo sapiens 3 0.7963
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7952
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7942
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7912
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7894
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7883
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7851
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 4 0.7842
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7839
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7806
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7770
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7703
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7660
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7659
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7655
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7630
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7626
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7623
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7623
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7608
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7599
Major histocompatibility complex class I-related gene protein Q95460 HMR1_HUMAN Homo sapiens 4 0.7541
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7541
Protein mono-ADP-ribosyltransferase PARP14 Q460N5 PAR14_HUMAN Homo sapiens 3 0.7539
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7510
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7501
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7495
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7489
Uroporphyrinogen-III C-methyltransferase P21631 SUMT_SINSX Sinorhizobium sp 4 0.7487
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.7459
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7429
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7422
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7420
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 4 0.7382
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7378
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7376
uroporphyrinogen-III C-methyltransferase P95417 P95417_PSEAI Pseudomonas aeruginosa 3 0.7368
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7364
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7360
Deoxyribodipyrimidine photo-lyase P61497 PHR_THET8 Thermus thermophilus 4 0.7338
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7337
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7333
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7332
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7329
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7309
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7293
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7283
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7278
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7271
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7268
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7258
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7236
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7222
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7221
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7220
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7204
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7189
Transitional endoplasmic reticulum ATPase P55072 TERA_HUMAN Homo sapiens 3 0.7170
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7130
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7128
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7125
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7124
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7123
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7101
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7094
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7090
mitogen-activated protein kinase kinase Q7YTF7 Q7YTF7_PLAF7 Plasmodium falciparum 4 0.7085
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7081
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7078
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7069
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7067
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7060
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7052
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7052
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7046
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7044
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7041

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