4'-prenyloxyderrone - Compound Card

4'-prenyloxyderrone

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4'-prenyloxyderrone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles CC(=CCOc1ccc(cc1)c1coc2c(c1=O)c(O)cc1c2C=CC(O1)(C)C)C
InChI InChI=1S/C25H24O5/c1-15(2)10-12-28-17-7-5-16(6-8-17)19-14-29-24-18-9-11-25(3,4)30-21(18)13-20(26)22(24)23(19)27/h5-11,13-14,26H,12H2,1-4H3
InChIKey QKOGFXYWPXGZNI-UHFFFAOYSA-N
Formula C25H24O5
HBA 5
HBD 1
MW 404.46
Rotatable Bonds 4
TPSA 68.9
LogP 5.69
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 404.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia oblata Leguminosae/Fabaceae Plantae 3090232

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]
Pubchem: 102236790

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(cc2)c1c(c23)occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 404.46 g/mol

Structure

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

Level: 0

Mol. Weight: 404.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 404.46 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.49
Plasma Protein Binding
77.65
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.57
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.09
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.69
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
-22.85
Rat (Acute)
2.84
Rat (Chronic Oral)
1.78
Fathead Minnow
5.65
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
495.75
Hydration Free Energy
-5.5
Log(D) at pH=7.4
4.6
Log(P)
6.66
Log S
-6.55
Log(Vapor Pressure)
-9.25
Melting Point
192.19
pKa Acid
8.58
pKa Basic
5.68
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 0.8980
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8980
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8945
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8945
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8942
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8942
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8766
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8766
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8759
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8759
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8530
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8530
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8523
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8523
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8498
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8498
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8480
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8480
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8423
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8423
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8388
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8388
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8350
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8350
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8146
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8146
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8101
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8101
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8098
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8098
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8038
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8038
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8020
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8020
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8009
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8009
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7995
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7995
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7959
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7959
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7897
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7897
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7853
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7853
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7765
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7765
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7749
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7749
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7692
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7692
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7678
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7678
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7667
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7667
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7623
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7623
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7597
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7597
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7578
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7578
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7559
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7559
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7558
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7558
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7532
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7532
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7531
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7531
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7530
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7530
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7524
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7524
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7447
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7447
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7443
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7443
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7442
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7442
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7437
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7437
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7431
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7431
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7421
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7421
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7410
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7410
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7374
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7374
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7373
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7373
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7364
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7364
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7339
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7339
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7318
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7318
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7315
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7315
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7301
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7301
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7300
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7300
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7280
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7280
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7237
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7237
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7232
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7232
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7226
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7226
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7224
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7224
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7217
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7217
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7215
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7215
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7204
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7204
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7196
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7196
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7190
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7190
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7186
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7186
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7174
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7174
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7157
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7157
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7141
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7141
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7130
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7130
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7119
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7119
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7118
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7118
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7109
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7109
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7081
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7081
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7066
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7066
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7062
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7062
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7058
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7058
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7054
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7054
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7046
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7046
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7038
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7038
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7027
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7027
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7019
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7019

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