8-methoxyneorautenol - Compound Card

8-methoxyneorautenol

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8-methoxyneorautenol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1cc2c(cc1O)OC1C2COc2c1cc1c(c2)OC(C=C1)(C)C
InChI InChI=1S/C21H20O5/c1-21(2)5-4-11-6-13-17(9-16(11)26-21)24-10-14-12-7-19(23-3)15(22)8-18(12)25-20(13)14/h4-9,14,20,22H,10H2,1-3H3
InChIKey DDBMMQROTYGJPU-UHFFFAOYSA-N
Formula C21H20O5
HBA 5
HBD 1
MW 352.39
Rotatable Bonds 1
TPSA 57.15
LogP 4.19
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 352.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina abyssinica Leguminosae/Fabaceae Plantae 1237573

Showing of synonyms

  • Yenesew A, Twinomuhwezi H, et al. (2009). 8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica.. Bulletin of the Chemical Society of Ethiopia,2009,23(2),205-210. [View] [PubMed]
Pubchem: 162947167

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC3C2COc4c3cc5c(c4)OCC=C5

Level: 0

Mol. Weight: 352.39 g/mol

Radical scavenging towards 2;2-diphenyl-1-picrylhydrazyl radical (dpph)

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.550
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
45.15
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
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
11.850
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.050
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.760
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.820
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
-2.330
Rat (Acute)
2.470
Rat (Chronic Oral)
1.800
Fathead Minnow
5.020
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
444.280
Hydration Free Energy
-6.890
Log(D) at pH=7.4
3.800
Log(P)
3.82
Log S
-5.32
Log(Vapor Pressure)
-8.22
Melting Point
190.83
pKa Acid
10.12
pKa Basic
5.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9640
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9640
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9454
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9454
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9318
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9318
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9261
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9261
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9059
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9059
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8780
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8780
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8676
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8676
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8386
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8386
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8334
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8334
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8324
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8324
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8324
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8324
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8276
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8276
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8252
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8252
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8216
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8216
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8060
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8060
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8058
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8058
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7951
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7951
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7933
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7933
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7932
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7932
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7893
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7893
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7864
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7864
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7778
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7778
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7775
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7775
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7752
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7752
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7743
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7743
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7738
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7738
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7682
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7682
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7656
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7656
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7636
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7636
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7631
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7631
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7609
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7609
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7564
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7564
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7564
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7564
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7556
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7556
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7530
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7530
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7495
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7495
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7485
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7485
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7437
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7437
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7422
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7422
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7405
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7405
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7321
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7321
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7321
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7321
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7319
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7319
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7315
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 3 0.7315
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7315
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 3 0.7315
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7306
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7306
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7276
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7276
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7251
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7251
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7247
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7247
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7245
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7245
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7244
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7244
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7237
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7237
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7229
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7229
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7211
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7211
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7210
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7210
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7208
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7208
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7184
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7184
ADP-ribosylation factor-like protein 3 A8ISN6 ARL3_CHLRE Chlamydomonas reinhardtii 4 0.7174
ADP-ribosylation factor-like protein 3 A8ISN6 ARL3_CHLRE Chlamydomonas reinhardtii 4 0.7174
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7163
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7163
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7149
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7149
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7145
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7145
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7118
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7118
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7115
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7115
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7111
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7111
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7109
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7109
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7102
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7102
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7092
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7092
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7088
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7088
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7078
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7078
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7075
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7075
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7057
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7057
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7054
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7054
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7053
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7053
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7041
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7041
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7038
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7038
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7038
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7038
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7015
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7015
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7013
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7013
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7011
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7011
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7009
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7009

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