Isofraxetin - Compound Card

Isofraxetin

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Isofraxetin

Structure
Zoomed Structure
  • Family: Plantae - Rhamnaceae
  • Kingdom: Plantae
  • Class: Coumarone
Canonical Smiles COc1cc2oc(=O)ccc2c(c1O)O
InChI InChI=1S/C10H8O5/c1-14-7-4-6-5(9(12)10(7)13)2-3-8(11)15-6/h2-4,12-13H,1H3
InChIKey ICFLIFNKWPXOAM-UHFFFAOYSA-N
Formula C10H8O5
HBA 5
HBD 2
MW 208.17
Rotatable Bonds 1
TPSA 79.9
LogP 1.21
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.1
Exact Mass 208.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Rhamnus disperma Rhamnaceae Plantae 1813078

Showing of synonyms

  • Marzouk M, El-Toumy S, et al. (1999). Polyphenolic metabolites of Rhamnus disperma. Phytochemistry, 1999, 52(5), 943-946. [View]
Pubchem: 10104491
Nmrshiftdb2: 60027150

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 208.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.380
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
55.32
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
9.410
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.090
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.480
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.550
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
3.670
Rat (Acute)
2.040
Rat (Chronic Oral)
2.610
Fathead Minnow
4.010
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
364.930
Hydration Free Energy
-10.500
Log(D) at pH=7.4
0.560
Log(P)
0.25
Log S
-2.89
Log(Vapor Pressure)
-5.01
Melting Point
203.43
pKa Acid
5.92
pKa Basic
5.68
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 0.9835
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9521
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9507
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9481
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9239
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9195
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9035
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9032
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8990
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8963
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8951
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.8943
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8826
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8800
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8766
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8748
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8741
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8651
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8634
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8615
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8575
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8550
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8529
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8511
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8496
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8489
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8457
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8427
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8398
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8375
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.8358
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 4 0.8334
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8333
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8306
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8285
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8271
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8267
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8256
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8252
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8235
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8232
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8228
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8205
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8188
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8185
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8180
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.8139
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8069
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8018
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8013
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7998
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7908
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 3 0.7905
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7895
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7872
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7858
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7844
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7837
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7834
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7799
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7778
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 4 0.7774
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7766
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 3 0.7763
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7757
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7708
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7700
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7691
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7673
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7617
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7602
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7575
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7562
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7502
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7499
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7490
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7488
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7485
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7483
Protein mono-ADP-ribosyltransferase PARP10 Q53GL7 PAR10_HUMAN Homo sapiens 3 0.7472
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7450
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7448
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7446
Uroporphyrinogen-III C-methyltransferase P21631 SUMT_SINSX Sinorhizobium sp 4 0.7415
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7388
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7384
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7382
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7372
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7368
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7364
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7355
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 4 0.7318
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7312
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7309
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7304
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase, chloroplastic Q9FYS3 HGGL_SECCE Secale cereale 3 0.7301
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7295
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7280
Major histocompatibility complex class I-related gene protein Q95460 HMR1_HUMAN Homo sapiens 4 0.7267
uroporphyrinogen-III C-methyltransferase P95417 P95417_PSEAI Pseudomonas aeruginosa 3 0.7254
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7247
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7247
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7247
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7222
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7208
Deoxyribodipyrimidine photo-lyase P61497 PHR_THET8 Thermus thermophilus 4 0.7203
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7202
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7198
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7177
CalS8 Q8KNF6 Q8KNF6_MICEC Micromonospora echinospora 4 0.7169
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7156
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7149
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7140
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7129
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7110
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7090
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7077
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7075
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1b, chloroplastic Q1XH05 HGL1B_WHEAT Triticum aestivum 3 0.7071
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7064
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7062
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7059
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7056
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7051
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7031
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7028
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7021
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7013
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 4 0.7012
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7002

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