Isoerythrinin A 4'-(3-methylbut-2-enyl) ether - Compound Card

Isoerythrinin A 4'-(3-methylbut-2-enyl) ether

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Isoerythrinin A 4'-(3-methylbut-2-enyl) ether

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles CC(=CCOc1ccc(cc1)c1coc2c(c1=O)ccc1c2C=CC(O1)(C)C)C
InChI InChI=1S/C25H24O4/c1-16(2)12-14-27-18-7-5-17(6-8-18)21-15-28-24-19-11-13-25(3,4)29-22(19)10-9-20(24)23(21)26/h5-13,15H,14H2,1-4H3
InChIKey KMTVRFNKQCNYOQ-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
2 Millettia dura Leguminosae/Fabaceae Plantae 62119
3 Millettia dura Leguminosae/Fabaceae Plantae 62119
4 Millettia dura Leguminosae/Fabaceae Plantae 62119
5 Millettia dura Leguminosae/Fabaceae Plantae 62119
6 Millettia dura Leguminosae/Fabaceae Plantae 62119
7 Millettia dura Leguminosae/Fabaceae Plantae 62119

Showing of synonyms

  • Derese S, Barasa L, et al. (2014). 4'-Prenyloxyderrone from the stem bark of Millettia oblata ssp. teitensis and the antiplasmodial activities of isoflavones from some Millettia species.. Phytochemistry Letters,2014,31(8),69-72. [View] [PubMed]
  • Derese S, Yenesew A, et al. (2003). A new isoflavone from stem bark of Millettia dura. Bulletin of the Chemical Society of Ethiopia,2003,17(1),113-115. [View] [PubMed]
  • Buyinza D, Chalo DM, et al. (2020). Flavonoids and Isoflavonoids of Millettia dura and Millettia ferruginea: Phytochemical review and chemotaxonomic values. Biochemical Systematics and Ecology, 2020, 91, 104053. [View]
  • Yenesew A, Midiwo JO, et al. (1996). Four isoflavones from seed pods of Millettia dura. Phytochemistry,1996,41(3),951-955. [View] [PubMed]
  • Marco M, Deyou T, et al. (2016). Pterocarpans and Isoflavones from the Root Bark of Millettia micans and of Millettia dura. Advances in Drug Discovery and Development,2016,1,1-8. [View] [PubMed]
  • Marco M, Deyou T, et al. (2017). Pterocarpans and isoflavones from the root bark of Millettia micans and of Millettia dura.. Phytochemistry Letters,2017,21,216-220.. [View] [PubMed]
  • Marco M, Deyou T, et al. (2016). Pterocarpans and isoflavones from the root bark of Millettia micans and of Millettia dura.. Advances in Drug Discovery and Development, 2016, 1-8. [View] [PubMed]
Pubchem: 7330539
Nmrshiftdb2: 70035644

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(cc2)c1c(c23)occ(c3=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

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.96
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.66
Plasma Protein Binding
79.77
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.24
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.96
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
-14.47
Rat (Acute)
2.55
Rat (Chronic Oral)
1.54
Fathead Minnow
5.75
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
485.11
Hydration Free Energy
-5.94
Log(D) at pH=7.4
4.36
Log(P)
6.49
Log S
-6.63
Log(Vapor Pressure)
-8.51
Melting Point
149.97
pKa Acid
9.81
pKa Basic
5.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8856
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8856
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8853
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8853
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8461
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8461
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8433
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8433
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8422
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8422
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8135
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8135
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8049
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8049
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8036
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8036
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7915
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7915
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7914
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7914
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7815
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7815
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7789
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7789
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7745
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7745
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7690
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7690
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7690
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7690
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7654
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7654
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7653
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7653
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7609
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7609
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7604
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7604
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7596
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7596
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7575
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7575
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7510
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7510
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7483
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7483
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7470
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7470
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7451
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7451
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7442
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7442
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7428
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7428
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7425
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7425
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7414
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7414
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7408
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7408
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7381
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7381
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7379
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7379
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7377
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7377
Poly [ADP-ribose] polymerase tankyrase-1 O95271 TNKS1_HUMAN Homo sapiens 4 0.7376
Poly [ADP-ribose] polymerase tankyrase-1 O95271 TNKS1_HUMAN Homo sapiens 4 0.7376
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7374
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7374
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7366
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7366
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7334
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7334
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7333
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7333
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7322
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7322
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7296
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7296
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7287
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7287
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7282
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7282
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7264
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7264
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7251
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7251
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7244
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7244
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7241
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7241
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7241
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7241
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7232
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7232
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7226
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7226
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7204
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7204
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7158
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7158
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7147
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7147
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7144
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7144
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7129
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7129
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7121
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7121
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7105
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7105
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7080
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7080
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7042
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7042
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7030
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7030
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7025
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7025
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7023
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7023
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7014
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7014

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