Isoerythrin-A-4"-prenyl ether - Compound Card

Isoerythrin-A-4"-prenyl ether

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Isoerythrin-A-4"-prenyl ether

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles CC(=CCOc1cccc(c1)c1cc(=O)c2c(o1)c1C=CC(Oc1cc2)(C)C)C
InChI InChI=1S/C25H24O4/c1-16(2)11-13-27-18-7-5-6-17(14-18)23-15-21(26)19-8-9-22-20(24(19)28-23)10-12-25(3,4)29-22/h5-12,14-15H,13H2,1-4H3
InChIKey JYANNSJCXISVEV-UHFFFAOYSA-N
Formula C25H24O4
HBA 4
HBD 0
MW 388.46
Rotatable Bonds 4
TPSA 48.67
LogP 5.99
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 388.17
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia dura Leguminosae/Fabaceae Plantae 62119

Showing of synonyms

  • Buyinza D, Yang LJ, et al. (2021). Cytotoxicity of isoflavones from Millettia dura. Natural product research, 2021, 35(16), 2744–2747. [View]

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(cc2)c1c(c23)oc(cc3=O)-c4ccccc4

Level: 1

Mol. Weight: 388.46 g/mol

Structure

SMILES: O=c1ccoc(c12)c3c(cc2)OCC=C3

Level: 0

Mol. Weight: 388.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 388.46 g/mol

Anticancer

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
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)
1.63
Plasma Protein Binding
87.68
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
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.71
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.55
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
-13.66
Rat (Acute)
2.44
Rat (Chronic Oral)
1.41
Fathead Minnow
5.67
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
489.21
Hydration Free Energy
-6.09
Log(D) at pH=7.4
5.01
Log(P)
6.47
Log S
-6.76
Log(Vapor Pressure)
-8.31
Melting Point
144.48
pKa Acid
10.06
pKa Basic
6.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9649
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9605
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9121
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8984
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8912
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8818
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8754
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8739
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8737
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8710
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8682
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8681
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8571
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8461
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8458
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8443
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8381
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8339
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8249
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8239
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8078
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7999
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7963
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7953
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7946
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7886
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7873
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7838
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7805
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7781
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7781
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7777
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7769
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7750
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7724
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7716
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7703
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7698
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7672
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7661
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7635
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7633
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7631
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 2 0.7624
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7620
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7610
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7606
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7566
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7549
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7546
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7545
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7520
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7513
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7494
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7475
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7472
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7468
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7453
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7435
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7428
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7414
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7398
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7397
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7395
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7380
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7368
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7367
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7355
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7344
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7334
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7325
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7320
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7305
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7301
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7282
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7273
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7263
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7256
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7250
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7246
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7236
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7230
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7223
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7220
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7219
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7209
Squalene--hopene cyclase P33247 SQHC_ALIAD Alicyclobacillus acidocaldarius subsp. acidocaldarius 4 0.7195
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7194
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7171
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7168
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7162
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7152
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7150
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7149
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7142
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7116
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7101
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7088
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7071
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7067
4-hydroxyphenylpyruvate dioxygenase P93836 HPPD_ARATH Arabidopsis thaliana 3 0.7064
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7053
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7045
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7040
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 2 0.7040
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7032
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7031
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7025
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7014
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7009
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7006

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