Rotenolone

Details

• Internal ID: 8147e79d-85dc-4edc-a49d-83f1ef8d42ff
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (1R,6R,13R)-13-hydroxy-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=C5C4(C3=O)O)OC)OC
• SMILES (Isomeric): CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@]4(C3=O)O)OC)OC
• InChI: InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1
• InChI Key: JFVKWCYZKMUTLH-AYPBNUJASA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.40 g/mol
• Exact Mass: 410.13655304 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 12a-Hydroxyrotenone
• Rotenalone
• Rotenolone I
• 509-96-6
• Rotenolon I
• 6a-beta,12a-beta-Rotenolone
• (-)-cis-Rotenolone
• 6ab,12ab-Rotenolone
• CHEBI:68051
• HN2R8MKH6Y
• (-)-cis-12a-Hydroxyrotenone
• 12-Hydroxyrotenone
• (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6ah)-one, 1,2,12,12a-alpha-tetrahydro-6a-alpha-hydroxy-2-alpha-isopropenyl-8,9-dimethoxy-
• (1R,6R,13R)-13-hydroxy-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
• [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aR,12aR)-
• 12alpha-Hydroxyrotenone
• UNII-HN2R8MKH6Y
• (-)-12alpha-Hydroxyrotenone
• CHEMBL240545
• BDBM50480247
• hydroxy-isopropenyl-dimethoxy-[?]one
• AKOS040753816
• LS-39367
• HY-119694
• C10464
• Q27104952
• (1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one
• (2R,6aR,12aR)-1,2,12,12a-Tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
• 1,2,12,12a-Tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6aR,12aR)-[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.5300	53.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7360	73.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7934	79.34%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6307	63.07%
P-glycoprotein inhibitior	+	0.7598	75.98%
P-glycoprotein substrate	+	0.5344	53.44%
CYP3A4 substrate	+	0.6477	64.77%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.7161	71.61%
CYP3A4 inhibition	+	0.6499	64.99%
CYP2C9 inhibition	-	0.7352	73.52%
CYP2C19 inhibition	+	0.7237	72.37%
CYP2D6 inhibition	-	0.9080	90.80%
CYP1A2 inhibition	+	0.6705	67.05%
CYP2C8 inhibition	-	0.6041	60.41%
CYP inhibitory promiscuity	-	0.5178	51.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6777	67.77%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.5403	54.03%
Skin irritation	-	0.7537	75.37%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.7354	73.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7770	77.70%
Micronuclear	+	0.5459	54.59%
Hepatotoxicity	-	0.5051	50.51%
skin sensitisation	-	0.6691	66.91%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.6006	60.06%
Acute Oral Toxicity (c)	II	0.5041	50.41%
Estrogen receptor binding	+	0.8547	85.47%
Androgen receptor binding	+	0.5652	56.52%
Thyroid receptor binding	+	0.8037	80.37%
Glucocorticoid receptor binding	+	0.7605	76.05%
Aromatase binding	+	0.5626	56.26%
PPAR gamma	+	0.8686	86.86%
Honey bee toxicity	+	0.5884	58.84%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9784	97.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.09%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.63%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.49%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.52%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.21%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.35%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.27%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.36%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.94%	89.00%
CHEMBL4208	P20618	Proteasome component C5	87.00%	90.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.85%	97.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.53%	97.14%
CHEMBL1951	P21397	Monoamine oxidase A	86.33%	91.49%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	86.01%	96.86%
CHEMBL2535	P11166	Glucose transporter	85.88%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.86%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.95%	91.19%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.83%	89.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.91%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.73%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.27%	93.40%

Plants that contains it

• Achillea cretica
• Ageratina riparia
• Amorpha fruticosa
• Antheroporum pierrei
• Cordia americana
• Derris trifoliata
• Erycibe expansa
• Glycosmis lanceolata
• Indigofera spicata
• Lonchocarpus subglaucescens
• Millettia ferruginea
• Millettia pachycarpa
• Mundulea chapelieri
• Neorautanenia mitis
• Patrinia scabra
• Pedicularis semitorta
• Pongamiopsis pervilleana
• Sarcolobus globosus
• Scopolia japonica
• Tephrosia candida
• Tephrosia praecana
• Tephrosia vogelii

Cross-Links

• PubChem: 68184
• NPASS: NPC152477
• ChEMBL: CHEMBL240545
• LOTUS: LTS0095984
• wikiData: Q27104952