Rotenonic acid

Details

• Internal ID: a612609d-c782-4335-991d-fc081063e7b3
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one
• InChI: InChI=1S/C23H24O6/c1-12(2)5-6-13-16(24)8-7-14-22(25)21-15-9-18(26-3)19(27-4)10-17(15)28-11-20(21)29-23(13)14/h5,7-10,20-21,24H,6,11H2,1-4H3/t20-,21+/m1/s1
• InChI Key: GBVCHRDRVDOMQV-RTWAWAEBSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₆
• Molecular Weight: 396.40 g/mol
• Exact Mass: 396.15728848 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 70191-71-8
• (6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one
• (6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-chromeno(3,4-b)chromen-12-one
• RefChem:179948
• (6aS,12aS)-6a,12a-Dihydro-9-hydroxy-2,3-dimethoxy-8-(3-methyl-2-buten-1-yl)[1]benzopyrano[3,4-b][1]benzopyran-12(6H)-one
• KBio2_001127
• Spectrum_000647
• SpecPlus_000073
• Spectrum2_000396
• Spectrum3_000195
• Spectrum4_001512
• Spectrum5_000303
• BSPBio_001749
• KBioGR_002203
• KBioSS_001127
• SPECTRUM200851
• DivK1c_006169
• SCHEMBL752362
• SPBio_000611
• CHEMBL2181295
• SCHEMBL30772485
• CHEBI:92599
• KBio1_001113
• KBio2_003695
• KBio2_006263
• KBio3_001249
• GBVCHRDRVDOMQV-RTWAWAEBSA-N
• CCG-38667
• MSK181238
• SDCCGMLS-0066410.P001
• H41633
• BRD-K34330170-001-01-8
• Q27164316
• (6aS,12aS)-9-Hydroxy-2,3-dimethoxy-8-(3-methyl-2-butenyl)-6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one
• (6aS,12aS)-9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-[1]benzopyrano[3,4-b][1]benzopyran-12-one
• Rotenonic acid; Rot-2'-enonic acid; 6a,12a-Dihydro-9-hydroxy-2,3-dimethoxy-8-(3-methyl-2-buten-1-yl)[1]benzopyrano[3,4-b][1]benzopyran-12(6H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.7777	77.77%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7494	74.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8745	87.45%
P-glycoprotein inhibitior	+	0.8607	86.07%
P-glycoprotein substrate	-	0.5466	54.66%
CYP3A4 substrate	+	0.6192	61.92%
CYP2C9 substrate	-	0.7880	78.80%
CYP2D6 substrate	-	0.7350	73.50%
CYP3A4 inhibition	-	0.6921	69.21%
CYP2C9 inhibition	-	0.5928	59.28%
CYP2C19 inhibition	+	0.8334	83.34%
CYP2D6 inhibition	-	0.6506	65.06%
CYP1A2 inhibition	+	0.7750	77.50%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.5920	59.20%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7729	77.29%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.7392	73.92%
Skin irritation	-	0.7973	79.73%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7005	70.05%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.7469	74.69%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6028	60.28%
Acute Oral Toxicity (c)	III	0.6268	62.68%
Estrogen receptor binding	+	0.9571	95.71%
Androgen receptor binding	+	0.7439	74.39%
Thyroid receptor binding	+	0.6956	69.56%
Glucocorticoid receptor binding	+	0.8202	82.02%
Aromatase binding	-	0.5572	55.72%
PPAR gamma	+	0.8285	82.85%
Honey bee toxicity	+	0.5959	59.59%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9577	95.77%

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	99.12%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.96%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.63%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.30%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.01%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.47%	93.40%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.60%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.50%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.74%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.63%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.14%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.15%	92.62%
CHEMBL2535	P11166	Glucose transporter	84.13%	98.75%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.54%	82.67%
CHEMBL3401	O75469	Pregnane X receptor	83.38%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.09%	99.15%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.10%	92.38%

Plants that contains it

• Derris taiwaniana

Cross-Links

• PubChem: 6708539
• LOTUS: LTS0088181
• wikiData: Q27164316