Phaseollin - Compound Card

Phaseollin

Select a section from the left sidebar

Phaseollin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Pterocarpan
Canonical Smiles Oc1ccc2c(c1)OC[C@@H]1[C@H]2Oc2c1ccc1c2C=CC(O1)(C)C
InChI InChI=1S/C20H18O4/c1-20(2)8-7-14-16(24-20)6-5-12-15-10-22-17-9-11(21)3-4-13(17)19(15)23-18(12)14/h3-9,15,19,21H,10H2,1-2H3/t15-,19-/m0/s1
InChIKey LWTDZKXXJRRKDG-KXBFYZLASA-N
Formula C20H18O4
HBA 4
HBD 1
MW 322.36
Rotatable Bonds 0
TPSA 47.92
LogP 4.19
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 322.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina abyssinica Leguminosae/Fabaceae Plantae 1237573
2 Erythrina burttii Leguminosae/Fabaceae Plantae 2590687

Showing of synonyms

  • Taniguchi M, Kubo I. (1993). Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.. Journal of Natural Products,1993,56(9),1539-1546. [View] [PubMed]
  • Yenesew A, Midiwo JO, et al. (2002). Three isoflav-3-enes and a 2-arylbenzofuran from the root bark of Erythrina burttii.. Phytochemistry,2002,59(3),337-341. [View] [PubMed]
Pubchem: 91572
Kegg Ligand: C10514
Nmrshiftdb2: 70129020
Bindingdb: 50317438
CPRiL: 429357
Structure

SMILES: C1=CCOc(cc2)c1c(c23)OC4C3COc5c4cccc5

Level: 0

Mol. Weight: 322.36 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.060
Plasma Protein Binding
80.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
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
9.720
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.750
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.300
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.630
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
1.240
Rat (Acute)
2.590
Rat (Chronic Oral)
1.710
Fathead Minnow
4.640
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
443.420
Hydration Free Energy
-7.760
Log(D) at pH=7.4
3.920
Log(P)
4.28
Log S
-5.13
Log(Vapor Pressure)
-8.47
Melting Point
195.7
pKa Acid
10.3
pKa Basic
6.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9467
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9467
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9438
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9438
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9421
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9421
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9311
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9311
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9274
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9274
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8681
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8681
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8649
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8649
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8621
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8621
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8588
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8588
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8512
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8512
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8440
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8440
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8307
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8307
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8165
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8165
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.8150
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.8150
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8146
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8146
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7923
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7923
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7905
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7905
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7867
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7867
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7841
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7841
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7770
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7770
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7766
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7766
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7729
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7729
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7728
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7728
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7721
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7721
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7655
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7655
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7638
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7638
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7625
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7625
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7621
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7621
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7573
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7573
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7540
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7540
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7495
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7495
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7494
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7494
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7480
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7480
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7430
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7430
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7405
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7405
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7376
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7376
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7373
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7373
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7357
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7357
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7354
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7354
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7340
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7340
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7329
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7329
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7301
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7301
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7285
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7285
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7272
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7272
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 3 0.7270
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 3 0.7270
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7261
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7261
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7246
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7246
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7242
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7242
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7229
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7229
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7222
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7222
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7209
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7209
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7203
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7203
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7198
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7198
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7197
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7197
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7191
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7191
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7181
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7181
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7171
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7171
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 3 0.7168
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 3 0.7168
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7165
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7165
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7160
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7160
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7159
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7159
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7143
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7143
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7127
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7127
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7090
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7090
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7089
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7089
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7062
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7062
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7061
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7061
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7038
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7038
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7019
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7019
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7018
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7018

Download SDF