Sumatrol - Compound Card

Sumatrol

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Sumatrol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2OC[C@@H]3[C@H](c2cc1OC)C(=O)c1c(O3)c2C[C@@H](Oc2cc1O)C(=C)C
InChI InChI=1S/C23H22O7/c1-10(2)14-6-12-16(29-14)7-13(24)21-22(25)20-11-5-17(26-3)18(27-4)8-15(11)28-9-19(20)30-23(12)21/h5,7-8,14,19-20,24H,1,6,9H2,2-4H3/t14-,19-,20+/m1/s1
InChIKey ZPEHYKMRUBEPSQ-XMCHAPAWSA-N
Formula C23H22O7
HBA 7
HBD 1
MW 410.42
Rotatable Bonds 3
TPSA 83.45
LogP 3.41
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 Tephrosia villosa Leguminosae/Fabaceae Plantae 62125

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: 442824
Kegg Ligand: C10532
Chebi: 9358
Nmrshiftdb2: 60062052

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)ccc3c2OC4C(C3=O)c5c(OC4)cccc5

Level: 0

Mol. Weight: 410.42 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.89
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.340
Plasma Protein Binding
79.41
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
13.720
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.940
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.260
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.990
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
-50.910
Rat (Acute)
2.960
Rat (Chronic Oral)
2.050
Fathead Minnow
5.010
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
482.780
Hydration Free Energy
-4.060
Log(D) at pH=7.4
3.390
Log(P)
4.29
Log S
-5.87
Log(Vapor Pressure)
-9.23
Melting Point
211.09
pKa Acid
8.09
pKa Basic
2.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8974
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8974
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8963
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8963
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8932
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8932
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8845
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8845
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8593
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8593
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8515
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8515
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8410
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8410
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8403
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8403
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8338
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8338
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8299
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8299
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8267
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8267
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8127
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8127
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7984
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7984
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7957
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7957
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7952
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7952
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7879
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7879
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7719
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7719
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7668
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7668
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7667
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7667
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7644
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7644
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7615
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7615
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7577
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7577
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7567
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7567
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7534
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7534
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7532
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7532
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7528
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 4 0.7528
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7528
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 4 0.7528
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7517
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7517
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7434
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7434
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7424
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7424
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7374
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7374
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7347
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7347
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7324
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7324
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7294
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7294
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7268
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7268
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7212
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7212
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 4 0.7202
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 4 0.7202
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7137
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7137
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7097
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7097
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7066
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7066
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7041
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7041
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7022
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7022
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7012
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7012

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