Tephrosin - Compound Card

Tephrosin

Select a section from the left sidebar

Tephrosin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2c(cc1OC)OC[C@@H]1[C@@]2(O)C(=O)c2c(O1)c1C=CC(Oc1cc2)(C)C
InChI InChI=1S/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1
InChIKey AQBZCCQCDWNNJQ-AUSIDOKSSA-N
Formula C23H22O7
HBA 7
HBD 1
MW 410.42
Rotatable Bonds 2
TPSA 83.45
LogP 3.11
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 410.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia dura Leguminosae/Fabaceae Plantae 62119
2 Millettia dura Leguminosae/Fabaceae Plantae 62119
3 Milletia dura Leguminosae/Fabaceae Plantae 1369122
4 Derris trifoliata Leguminosae/Fabaceae Plantae 185716
5 Derris trifoliata Leguminosae/Fabaceae Plantae 185716
6 Derris trifoliata Leguminosae/Fabaceae Plantae 185716
7 Tephrosia vogelii Leguminosae/Fabaceae Plantae 1157238
8 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]
  • Yenesew A, Midiwo JO, et al. (1997). 6-Methoxycalpogonium Isoflavone A: A New Isoflavone from the Seed Pods of Millettia dura.. Journal of Natural Products,1997,60(8),806–807. [View] [PubMed]
  • Yenesew AB, Twinomuhwezi H, et al. (2009). Antiplasmodial and larvicidal flavonoids from Derris trifoliata.. Bulletin of the Chemical Society of Ethiopia,2009,23(3),409-414. [View] [PubMed]
  • Stevenson PC, Kite GC, et al. (2012). Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment.. Phytochemistry,2012(78),135-146. [View] [PubMed]
  • Yenesew A, Derese S, et al. (2003). Effect of rotenoids from the seeds of Millettia dura on larvae of Aedes aegypti.. Pest Management Science,2003,59(10),1159-1161. [View] [PubMed]
  • Yenesew A, Kiplagat JT Mushibe EK Derese S, et al. (2005). Rotenoid derivatives from Kenyan Millettia and Derris species as larvicidal agents. Natural products and drug discovery, Proceedings of the 11th NAPRECA Symposium August 9-12, 2005, Hôtel Panorama, Antananarivo, Madagascar. [View] [PubMed]
  • Yenesew A1, Kiplagat JT, et al. (2006). Two unusual rotenoid derivatives, 7a-O-methyl-12a-hydroxydeguelol and spiro-13-homo-13-oxaelliptone, from the seeds of Derris trifoliata.. Phytochemistry,2006,67(10):988-991. [View] [PubMed]
Pubchem: 114909
Kegg Ligand: C10535
Chebi: 9442
Nmrshiftdb2: 60069148
Metabolights: MTBLC9442
Bindingdb: 50505206
CPRiL: 74579
Structure

SMILES: C1=CCOc2ccc(c3c12)C(=O)C4c5c(OCC4O3)cccc5

Level: 0

Mol. Weight: 410.42 g/mol

Anti-plasmodial
Larvicidal

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.230
Plasma Protein Binding
79.16
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.970
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.230
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.300
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.320
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
-34.420
Rat (Acute)
3.030
Rat (Chronic Oral)
1.760
Fathead Minnow
4.900
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
463.350
Hydration Free Energy
-4.540
Log(D) at pH=7.4
3.190
Log(P)
3.22
Log S
-4.56
Log(Vapor Pressure)
-8.64
Melting Point
202.49
pKa Acid
8.16
pKa Basic
1.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9577
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9577
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8853
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8853
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8176
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8176
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8134
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8134
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7912
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7912
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7852
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7852
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7799
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7799
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7793
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7793
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7762
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7762
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7755
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7755
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7449
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7449
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7291
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7291
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7253
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7253
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7243
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7243
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7223
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7223
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7210
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7210
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7187
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7187
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7160
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7160
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7156
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7156
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7129
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7129
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7068
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7068
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7067
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7067

Download SDF