(+)-tephrodin - Compound Card

(+)-tephrodin

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(+)-tephrodin

Structure
Zoomed Structure
  • Family: Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles COc1cc2OC[C@@H]3[C@@](c2c2c1c(=O)cc(o2)c1ccccc1)(OC(=O)C)C(=O)C(O3)(C)C
InChI InChI=1S/C25H22O8/c1-13(26)32-25-19(33-24(2,3)23(25)28)12-30-18-11-17(29-4)20-15(27)10-16(31-22(20)21(18)25)14-8-6-5-7-9-14/h5-11,19H,12H2,1-4H3/t19-,25+/m1/s1
InChIKey WIYBTPVLDULURO-CLOONOSVSA-N
Formula C25H22O8
HBA 8
HBD 0
MW 450.44
Rotatable Bonds 3
TPSA 101.27
LogP 3.37
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 450.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354

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]
Pubchem: 101821118

No compound-protein relationship available.

Structure

SMILES: O=C1COC(C12)COc3c2c4c(cc3)c(=O)cc(o4)-c5ccccc5

Level: 1

Mol. Weight: 334.33 g/mol

Structure

SMILES: O=C1COC(C12)COc3c2c4c(cc3)c(=O)cco4

Level: 0

Mol. Weight: 258.23 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.410
Plasma Protein Binding
96.89
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.410
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.380
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.870
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.830
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
Safe
T. Pyriformis
-156.100
Rat (Acute)
3.120
Rat (Chronic Oral)
1.590
Fathead Minnow
5.500
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
514.380
Hydration Free Energy
-2.880
Log(D) at pH=7.4
2.830
Log(P)
3.31
Log S
-5.22
Log(Vapor Pressure)
-9.07
Melting Point
214.1
pKa Acid
7.13
pKa Basic
2.41
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9561
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9561
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9317
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9317
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8986
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8986
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8984
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8984
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8867
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8867
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8818
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8818
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8750
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8750
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8597
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8597
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8507
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8507
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8506
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8506
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8446
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8446
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8341
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8341
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8336
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8336
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8195
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8195
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8026
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8026
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7907
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7907
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7791
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7791
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7782
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7782
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7778
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7778
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7701
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7701
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7678
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7678
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7662
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7662
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7615
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7615
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7579
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7579
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7513
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7513
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7506
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7506
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7461
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7461
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7402
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7402
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7392
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7392
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7311
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7311
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7309
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7309
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7306
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7306
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7254
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7254
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7222
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7222
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7187
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7187
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7152
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7152
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7151
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7151
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7148
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7148
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7122
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7122
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7119
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7119
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7118
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7118
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7080
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7080
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7049
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7049
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7033
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7033
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7027
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7027
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7012
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7012
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7003
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7003

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