UCSF

ZINC03860715

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
October 3rd, 2005 29 Yes

Popular Name: Rotenone Rotenone

Find On: PubMed — Wikipedia — Google

CAS Numbers: 83-79-4 , [83-79-4]

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 3.59 8.74 -11.43 0 6 0 63 394.423 3 ↓

Vendor Notes

Note Type Comments Provided By
biological_source Constit. of the root of Derris elliptica . Widely distrib. in the Leguminosae (Papilionoideae) e.g. in many other Derris spp. Lonchocarpus spp. Millettia spp., Tephrosia spp. ZereneX Building Blocks
mp 153 MolMall (formerly Molecular Diversity Preservation International)
mp 159 MolMall (formerly Molecular Diversity Preservation International)
Purity 95% Fluorochem
Therapy acaricide, ectoparasiticide, antineoplastic, mitochondrial poison SMDC MicroSource
biological_use Antineoplastic agent IBScreen Bioactives IBScreen Bioactives
UniProt Database Links AOX1A_ARATH; NDB2_ARATH; NDB4_ARATH; NDI1_YEAST; TI171_ARATH; TI172_ARATH; TI173_ARATH; TI221_ARATH; TI223_ARATH; TI442_ARATH; TIM50_ARATH; TO204_ARATH; TO401_ARATH; TO402_ARATH; TOM72_ARATH ChEBI
biological_use Contact insecticide and pesticide IBScreen Bioactives
Patent Database Links EP1700845; US2004053786; US2004235959; US2005085555; US2006111403; US2007225336; US2007264299; US2008275061; WO2005118552; WO2006023783; WO2006055922; WO2007099151; WO2008150393; WO2008154528 ChEBI
mechanism Inhibits the transfer of electrons from Fe-S centers in Complex I to ubiquinone IBScreen Bioactives
biological_use Potent mitochondrial poison IBScreen Bioactives
PUBCHEM_PATENT_ID US4196073 IBM Patent Data

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
DUOX2-2-E Thyroid Oxidase 2 (cluster #2 Of 2), Eukaryotic Eukaryotes 5 0.40 Binding ≤ 10μM
NDUA4-2-E NADH-ubiquinone Oxidoreductase MLRQ Subunit (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUA6-2-E NADH-ubiquinone Oxidoreductase B14 Subunit (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUA8-2-E NADH-ubiquinone Oxidoreductase 19 KDa Subunit (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUAA-2-E NADH-ubiquinone Oxidoreductase 42 KDa Subunit (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUAB-2-E NADH-ubiquinone Oxidoreductase Subunit B14.7 (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUB5-2-E NADH-ubiquinone Oxidoreductase SGDH Subunit (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUB6-2-E NADH-ubiquinone Oxidoreductase B17 Subunit (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUB7-2-E NADH-ubiquinone Oxidoreductase B18 Subunit (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUS2-2-E NADH-ubiquinone Oxidoreductase 49 KDa Subunit (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NDUS8-2-E NADH-ubiquinone Oxidoreductase 23 KDa Subunit, (cluster #2 Of 2), Eukaryotic Eukaryotes 29 0.36 Binding ≤ 10μM
NU1M-1-E NADH-ubiquinone Oxidoreductase Chain 1 (cluster #1 Of 1), Eukaryotic Eukaryotes 2 0.42 Binding ≤ 10μM
NU2M-1-E NADH-ubiquinone Oxidoreductase Chain 2 (cluster #1 Of 1), Eukaryotic Eukaryotes 2 0.42 Binding ≤ 10μM
NU3M-1-E NADH-ubiquinone Oxidoreductase Chain 3 (cluster #1 Of 1), Eukaryotic Eukaryotes 2 0.42 Binding ≤ 10μM
NU4M-1-E NADH-ubiquinone Oxidoreductase Chain 4 (cluster #1 Of 1), Eukaryotic Eukaryotes 4 0.41 Binding ≤ 10μM
NU5M-1-E NADH-ubiquinone Oxidoreductase Chain 5 (cluster #1 Of 1), Eukaryotic Eukaryotes 2 0.42 Binding ≤ 10μM
NU6M-1-E NADH-ubiquinone Oxidoreductase Chain 6 (cluster #1 Of 1), Eukaryotic Eukaryotes 2 0.42 Binding ≤ 10μM
Z101775-1-O Drosophila (cluster #1 Of 1), Other Other 10000 0.24 Functional ≤ 10μM
Z50425-3-O Plasmodium Falciparum (cluster #3 Of 22), Other Other 10000 0.24 Functional ≤ 10μM
Z50531-3-O Caenorhabditis Elegans (cluster #3 Of 3), Other Other 2000 0.28 Functional ≤ 10μM
Z50531-1-O Caenorhabditis Elegans (cluster #1 Of 1), Other Other 2000 0.28 ADME/T ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
NDUA8_HUMAN P51970 NADH-ubiquinone Oxidoreductase 19 KDa Subunit, Human 28.8 0.36 Binding ≤ 1μM
NDUS8_HUMAN O00217 NADH-ubiquinone Oxidoreductase 23 KDa Subunit,, Human 28.8 0.36 Binding ≤ 1μM
NDUAA_HUMAN O95299 NADH-ubiquinone Oxidoreductase 42 KDa Subunit, Human 28.8 0.36 Binding ≤ 1μM
NDUS2_HUMAN O75306 NADH-ubiquinone Oxidoreductase 49 KDa Subunit, Human 28.8 0.36 Binding ≤ 1μM
NDUA6_HUMAN P56556 NADH-ubiquinone Oxidoreductase B14 Subunit, Human 28.8 0.36 Binding ≤ 1μM
NDUB6_HUMAN O95139 NADH-ubiquinone Oxidoreductase B17 Subunit, Human 28.8 0.36 Binding ≤ 1μM
NDUB7_HUMAN P17568 NADH-ubiquinone Oxidoreductase B18 Subunit, Human 28.8 0.36 Binding ≤ 1μM
NU1M_HUMAN P03886 NADH-ubiquinone Oxidoreductase Chain 1, Human 1.99526231 0.42 Binding ≤ 1μM
NU2M_HUMAN P03891 NADH-ubiquinone Oxidoreductase Chain 2, Human 1.99526231 0.42 Binding ≤ 1μM
NU3M_HUMAN P03897 NADH-ubiquinone Oxidoreductase Chain 3, Human 1.99526231 0.42 Binding ≤ 1μM
NU4M_HUMAN P03905 NADH-ubiquinone Oxidoreductase Chain 4, Human 1.99526231 0.42 Binding ≤ 1μM
NU5M_HUMAN P03915 NADH-ubiquinone Oxidoreductase Chain 5, Human 1.99526231 0.42 Binding ≤ 1μM
NU6M_HUMAN P03923 NADH-ubiquinone Oxidoreductase Chain 6, Human 1.99526231 0.42 Binding ≤ 1μM
NDUA4_HUMAN O00483 NADH-ubiquinone Oxidoreductase MLRQ Subunit, Human 28.8 0.36 Binding ≤ 1μM
NDUB5_HUMAN O43674 NADH-ubiquinone Oxidoreductase SGDH Subunit, Human 28.8 0.36 Binding ≤ 1μM
NDUAB_HUMAN Q86Y39 NADH-ubiquinone Oxidoreductase Subunit B14.7, Human 28.8 0.36 Binding ≤ 1μM
DUOX2_HUMAN Q9NRD8 Thyroid Oxidase 2, Human 5.1 0.40 Binding ≤ 1μM
NDUA8_HUMAN P51970 NADH-ubiquinone Oxidoreductase 19 KDa Subunit, Human 28.8 0.36 Binding ≤ 10μM
NDUS8_HUMAN O00217 NADH-ubiquinone Oxidoreductase 23 KDa Subunit,, Human 28.8 0.36 Binding ≤ 10μM
NDUAA_HUMAN O95299 NADH-ubiquinone Oxidoreductase 42 KDa Subunit, Human 28.8 0.36 Binding ≤ 10μM
NDUS2_HUMAN O75306 NADH-ubiquinone Oxidoreductase 49 KDa Subunit, Human 28.8 0.36 Binding ≤ 10μM
NDUA6_HUMAN P56556 NADH-ubiquinone Oxidoreductase B14 Subunit, Human 28.8 0.36 Binding ≤ 10μM
NDUB6_HUMAN O95139 NADH-ubiquinone Oxidoreductase B17 Subunit, Human 28.8 0.36 Binding ≤ 10μM
NDUB7_HUMAN P17568 NADH-ubiquinone Oxidoreductase B18 Subunit, Human 28.8 0.36 Binding ≤ 10μM
NU1M_HUMAN P03886 NADH-ubiquinone Oxidoreductase Chain 1, Human 1.99526231 0.42 Binding ≤ 10μM
NU2M_HUMAN P03891 NADH-ubiquinone Oxidoreductase Chain 2, Human 1.99526231 0.42 Binding ≤ 10μM
NU3M_HUMAN P03897 NADH-ubiquinone Oxidoreductase Chain 3, Human 1.99526231 0.42 Binding ≤ 10μM
NU4M_HUMAN P03905 NADH-ubiquinone Oxidoreductase Chain 4, Human 1.99526231 0.42 Binding ≤ 10μM
NU5M_HUMAN P03915 NADH-ubiquinone Oxidoreductase Chain 5, Human 1.99526231 0.42 Binding ≤ 10μM
NU6M_HUMAN P03923 NADH-ubiquinone Oxidoreductase Chain 6, Human 1.99526231 0.42 Binding ≤ 10μM
NDUA4_HUMAN O00483 NADH-ubiquinone Oxidoreductase MLRQ Subunit, Human 28.8 0.36 Binding ≤ 10μM
NDUB5_HUMAN O43674 NADH-ubiquinone Oxidoreductase SGDH Subunit, Human 28.8 0.36 Binding ≤ 10μM
NDUAB_HUMAN Q86Y39 NADH-ubiquinone Oxidoreductase Subunit B14.7, Human 28.8 0.36 Binding ≤ 10μM
DUOX2_HUMAN Q9NRD8 Thyroid Oxidase 2, Human 5.1 0.40 Binding ≤ 10μM
Z50531 Z50531 Caenorhabditis Elegans 2000 0.28 Functional ≤ 10μM
Z101775 Z101775 Drosophila 10000 0.24 Functional ≤ 10μM
Z50425 Z50425 Plasmodium Falciparum 10000 0.24 Functional ≤ 10μM
Z50531 Z50531 Caenorhabditis Elegans 2000 0.28 ADME/T ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
Respiratory electron transport

Analogs ( Draw Identity 99% 90% 80% 70% )