8-prenylluteone - Compound Card

8-prenylluteone

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8-prenylluteone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavonoid
Canonical Smiles CC(=CCc1c(O)c(CC=C(C)C)c2c(c1O)c(=O)c(co2)c1ccc(cc1O)O)C
InChI InChI=1S/C25H26O6/c1-13(2)5-8-17-22(28)18(9-6-14(3)4)25-21(23(17)29)24(30)19(12-31-25)16-10-7-15(26)11-20(16)27/h5-7,10-12,26-29H,8-9H2,1-4H3
InChIKey VYELCIXMHUBNAL-UHFFFAOYSA-N
Formula C25H26O6
HBA 6
HBD 4
MW 422.48
Rotatable Bonds 5
TPSA 111.13
LogP 5.3
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 422.17
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina burttii Leguminosae/Fabaceae Plantae 2590687
2 Erythrina senegalensis Leguminosae/Fabaceae Plantae 157649

Showing of synonyms

  • Oh WK, Lee C, et al. (2009). Diacylglycerol acyltransferase-inhibitory compounds from Erythrina senegalensis.. Archives of pharmacal research,2009, 32(1), 43-47. [View] [PubMed]
  • Yenesew A, Irungu B, et al. (2003). Two prenylated flavonoids from the stem bark of Erythrina burttii.. Phytochemistry,2003,63(4),445-448. [View] [PubMed]
Pubchem: 471687
Nmrshiftdb2: 70008214

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 422.48 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 422.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 422.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.02
Plasma Protein Binding
78.85
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
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.06
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.28
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.24
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.49
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-24.9
Rat (Acute)
2.32
Rat (Chronic Oral)
3.08
Fathead Minnow
5.41
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
529.25
Hydration Free Energy
-6.47
Log(D) at pH=7.4
4.05
Log(P)
6.37
Log S
-6.39
Log(Vapor Pressure)
-9.76
Melting Point
205.11
pKa Acid
6.29
pKa Basic
7.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9556
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9556
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9088
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9088
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8864
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8864
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8861
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8861
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8738
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8738
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8525
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8525
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8407
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8407
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8279
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8279
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8226
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8226
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8203
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8203
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8178
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8178
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8176
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8176
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8160
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8160
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8129
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8129
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8096
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8096
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8091
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8091
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8087
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8087
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8061
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8061
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8019
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8019
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8001
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8001
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7992
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7992
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7897
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7897
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7860
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7860
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7842
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7842
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7837
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7837
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7824
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7824
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7814
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7814
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7795
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7795
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7779
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7779
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7755
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7755
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7752
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7752
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7729
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7729
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7727
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7727
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7704
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7704
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7654
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7654
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7653
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7653
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7650
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7650
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7638
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7638
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7619
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7619
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7599
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7599
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7595
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7595
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7543
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7543
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7539
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7539
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7506
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7506
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7497
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7497
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7475
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7475
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7468
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7468
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7463
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7463
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7427
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7427
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7422
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7422
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7414
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7414
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7369
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7369
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7343
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7343
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7339
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7339
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7327
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7327
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7320
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7320
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7318
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7318
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7293
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7293
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7290
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7290
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7283
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7283
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7270
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7270
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7255
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7255
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7239
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7239
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7233
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7233
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7192
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7192
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7182
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7182
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7170
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7170
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7169
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7169
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7160
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7160
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7159
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7159
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7128
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7128
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7123
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7123
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7101
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7101
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7047
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7047
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7045
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7045
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7037
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7037
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7032
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7032
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7030
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7030
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7023
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7023
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7004
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7004

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