Derrone - Compound Card

Derrone

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Derrone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylated Isoflavonoid
Canonical Smiles Oc1ccc(cc1)c1coc2c(c1=O)c(O)cc1c2C=CC(O1)(C)C
InChI InChI=1S/C20H16O5/c1-20(2)8-7-13-16(25-20)9-15(22)17-18(23)14(10-24-19(13)17)11-3-5-12(21)6-4-11/h3-10,21-22H,1-2H3
InChIKey ZSYPWSSGRVZENH-UHFFFAOYSA-N
Formula C20H16O5
HBA 5
HBD 2
MW 336.34
Rotatable Bonds 1
TPSA 79.9
LogP 4.06
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 336.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354
2 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354
3 Bolusanthus speciosus Leguminosae/Fabaceae Plantae 53838

Showing of synonyms

  • Muiva-Mutisya L, Macharia B, et al. (2014). 6α-Hydroxy-α-toxicarol and (+)-tephrodin with antiplasmodial activities from Tephrosia species.. Phytochemistry Letters,2014,10,179-183. [View] [PubMed]
  • Erasto P, Bojase-Moleta G, et al. (2004). Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus.. Phytochemistry,2004,65(7),875-880. [View] [PubMed]
  • Atilaw Y, Muiva-Mutisya L, et al. (2017). Four Prenylflavone Derivatives with Antiplasmodial Activities from the Stem of Tephrosia purpurea subsp. Leptostachya. Molecules, 2017, 22(9), 1514. [View]
CPRiL: 248173
Structure

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

Level: 1

Mol. Weight: 336.34 g/mol

Structure

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

Level: 0

Mol. Weight: 336.34 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 336.34 g/mol

Anti-plasmodial
Antimicrobial
Radical scavenging against dpph

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.690
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.330
Plasma Protein Binding
71.94
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.090
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.680
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.960
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.630
Micronucleos
Toxic
NR-AhR
Toxic
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
Toxic
T. Pyriformis
2.450
Rat (Acute)
2.530
Rat (Chronic Oral)
2.260
Fathead Minnow
4.870
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
464.630
Hydration Free Energy
-10.690
Log(D) at pH=7.4
4.020
Log(P)
4.42
Log S
-5.7
Log(Vapor Pressure)
-8.91
Melting Point
274.23
pKa Acid
8.29
pKa Basic
5.04
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 0.9670
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9670
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9499
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9499
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9422
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9422
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9199
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9199
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9163
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9163
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9100
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9100
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9062
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9062
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8912
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8912
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8758
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8758
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8746
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8746
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8631
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8631
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
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8442
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8442
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8374
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8374
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8290
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8290
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8275
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8275
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8069
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8069
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8064
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8064
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8052
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8052
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8035
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8035
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7980
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7980
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7944
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7944
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7925
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7925
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7900
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7900
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7834
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7834
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7823
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7823
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7780
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7780
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7714
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7714
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7700
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.7700
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7665
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7665
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7659
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7659
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7606
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7606
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7604
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7604
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7563
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7563
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7557
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7557
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7547
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7547
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7539
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7539
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7536
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7536
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7521
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7521
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7464
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7464
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7409
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7409
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7408
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7408
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7397
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7397
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7370
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7370
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7350
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7350
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7340
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7340
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7313
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7313
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7307
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7307
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7298
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7298
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7287
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7287
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7266
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7266
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7236
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7236
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7233
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7233
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7228
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7228
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7204
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7204
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7187
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7187
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7185
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7185
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7185
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7185
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7181
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7181
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7160
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7160
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7155
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7155
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7149
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7149
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7115
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7115
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7098
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7098
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7074
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7074
Calmodulin-like domain protein kinase isoenzyme gamma, related F0V9W9 F0V9W9_NEOCL Neospora caninum 3 0.7071
Calmodulin-like domain protein kinase isoenzyme gamma, related F0V9W9 F0V9W9_NEOCL Neospora caninum 3 0.7071
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7060
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7060
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7051
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7051
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7048
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7048
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7042
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7042
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7042
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7042
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7039
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7039
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7034
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7034
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7002
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7002

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