Pisatin - Compound Card

Pisatin

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Pisatin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Pterocarpan
Canonical Smiles COc1ccc2c(c1)OC[C@]1([C@@H]2Oc2c1cc1c(c2)OCO1)O
InChI InChI=1S/C17H14O6/c1-19-9-2-3-10-12(4-9)20-7-17(18)11-5-14-15(22-8-21-14)6-13(11)23-16(10)17/h2-6,16,18H,7-8H2,1H3/t16-,17+/m1/s1
InChIKey LZMRDTLRSDRUSU-SJORKVTESA-N
Formula C17H14O6
HBA 6
HBD 1
MW 314.29
Rotatable Bonds 1
TPSA 66.38
LogP 2.14
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 314.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia macrophylla Leguminosae/Fabaceae Plantae 1712208
2 Tephrosia rhodesica Leguminosae/Fabaceae Plantae 556521

Showing of synonyms

  • Zingue S, Tchoumtchoua J, et al. (2016). Estrogenic and cytotoxic potentials of compounds isolated from Millettia macrophylla Benth (Fabaceae): towards a better understanding of its underlying mechanisms.. BMC complementary and alternative medicine,2016, 16(1), 421. [View] [PubMed]
  • Atilaw Y, Muiva-Mutisya L, et al. (2020). Prenylated Flavonoids from the Roots of Tephrosia rhodesica. Journal of natural products, 2020, 83(8), 2390–2398. [View]
Pubchem: 101689
Kegg Ligand: C10516
Chebi: 67347
Nmrshiftdb2: 60067840
Metabolights: MTBLC67347
Bindingdb: 50345340
CPRiL: 37529
Structure

SMILES: O1COc(c2)c1cc(c23)OC4C3COc5c4cccc5

Level: 0

Mol. Weight: 314.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.420
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
76.14
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
12.300
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.420
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.220
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.690
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
1.560
Rat (Acute)
2.260
Rat (Chronic Oral)
1.210
Fathead Minnow
4.580
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
406.750
Hydration Free Energy
-8.030
Log(D) at pH=7.4
2.610
Log(P)
2.58
Log S
-3.56
Log(Vapor Pressure)
-8.13
Melting Point
186.65
pKa Acid
10.14
pKa Basic
0.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9556
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9545
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.9285
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.9103
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8816
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8745
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8745
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8725
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.8710
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8708
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8700
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8648
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8625
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8559
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.8521
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8499
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8425
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8397
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8382
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8340
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8314
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.8292
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8274
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8274
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8273
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8257
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.8240
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8208
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8172
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8154
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8136
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8089
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8085
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.8078
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.8066
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8063
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8040
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8036
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8010
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8004
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7972
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7966
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7955
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7953
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7917
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7897
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7891
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7852
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7829
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7796
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7792
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7777
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7767
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7765
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7754
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7721
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7715
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7712
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7710
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7701
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7676
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7660
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7620
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7617
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7585
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7582
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7572
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7566
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7552
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7461
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7444
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7434
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7425
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7422
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7364
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7363
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7357
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7355
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7355
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7353
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7336
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7309
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7306
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7295
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7294
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7279
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7274
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7265
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7264
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7257
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7255
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7254
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7250
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7247
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7240
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7238
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7217
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7206
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7205
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7204
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7200
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7195
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7190
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7181
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7180
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7171
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7163
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7160
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7144
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7114
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7110
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7109
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7107
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 2 0.7102
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7086
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7085
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7083
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7080
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7071
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7070
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7069
Beta-adrenergic receptor kinase 1 P25098 ARBK1_HUMAN Homo sapiens 3 0.7069
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7060
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7049
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7038
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7019
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7018
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7018
RNA-directed RNA polymerase lambda-3 P0CK31 RDRP_REOVD Reovirus type 3 3 0.7006
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7002

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