5'beta-Rotenone

Details

• Internal ID: e4c65159-c372-4b4b-9ab8-20df051f91b1
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• SMILES (Canonical): CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC
• SMILES (Isomeric): CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC
• InChI: InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3
• InChI Key: JUVIOZPCNVVQFO-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₆
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.14163842 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 4.10

Synonyms

• Rotenona
• 12679-58-2
• 16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• Rotacide E.C.
• 5'.beta.-Rotenone
• [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2.alpha.,6a.alpha.,12a.alpha.)]-
• [2R-(2alpha,6a-alpha,12a-alpha)]-1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
• 7701-84-0
• Green cross warble
• (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6a.alpha.H)-one, 1,2,12,12a.alpha.-tetrahydro-2.alpha.-isopropenyl-8,9-dimethoxy-
• [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6a.alpha.H)-one, 1,2,12,12a.alpha.-tetrahydro-2.alpha.-isopropenyl-8,9-dimethoxy-
• Neuro_000013
• MLS006011865
• CHEMBL418710
• SCHEMBL9815546
• DTXSID10859127
• JUVIOZPCNVVQFO-UHFFFAOYSA-N
• NP139
• MFCD09025614
• NSC115907
• AKOS025247996
• NSC-115907
• NCGC00015901-02
• NCGC00095765-01
• SMR000444453
• SY102181
• VS-12311
• FT-0774778
• A864212
• (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-.alpha.-isopropenyl-8,9-dimethoxy-
• (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one,1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-,(2R,6aS,12aS)-
• (2R,2.alpha.,6a.alpha.,12a.alpha.)-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6aH)-one
• 16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0(3),(1)(1).0?,?.0(1)?,(1)?]henicosa-3,8,10,14,16,18-hexaen-12-one
• 2,6a,12,12a-tetrahydro-8,9-di methoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo [2,3-h][1]benzopyran-6 (1h)-one
• 2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-H]chromen-6(6ah)-one, (6R,-(6a.alpha.,12a.alpha.)-
• 8,9-Dimethoxy-2-(1-propen-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	79.4 nM	Potency	via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	794.3 nM	Potency	via Super-PRED
CHEMBL1293298	Q01453	Peripheral myelin protein 22	47.8 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	501.2 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	46.5 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	63.1 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	31.6 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	794.3 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	5 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.23%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.18%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.79%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.49%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.02%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.99%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.57%	94.80%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.56%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.90%	92.94%
CHEMBL2535	P11166	Glucose transporter	87.80%	98.75%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.28%	82.67%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.01%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.85%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.67%	97.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.49%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.22%	95.78%

Plants that contains it

• Antheroporum pierrei
• Derris elliptica
• Derris trifoliata
• Gardenia jasminoides
• Lonchocarpus salvadorensis
• Millettia pachycarpa
• Millettia pachyloba
• Mundulea chapelieri
• Pachyrhizus tuberosus
• Piscidia piscipula
• Spatholobus parviflorus
• Tephrosia macropoda
• Tephrosia strigosa
• Tephrosia villosa
• Tephrosia vogelii

Cross-Links

• PubChem: 5102
• LOTUS: LTS0222230
• wikiData: Q105031354