Kushenol I

Details

• Internal ID: 40f4af86-9bda-41f2-82c9-af8947d1de91
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2R,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC(CC1=C2C(=C(C=C1O)OC)C(=O)C(C(O2)C3=C(C=C(C=C3)O)O)O)C(=C)C)C
• SMILES (Isomeric): CC(=CC[C@H](CC1=C2C(=C(C=C1O)OC)C(=O)[C@@H]([C@H](O2)C3=C(C=C(C=C3)O)O)O)C(=C)C)C
• InChI: InChI=1S/C26H30O7/c1-13(2)6-7-15(14(3)4)10-18-20(29)12-21(32-5)22-23(30)24(31)26(33-25(18)22)17-9-8-16(27)11-19(17)28/h6,8-9,11-12,15,24,26-29,31H,3,7,10H2,1-2,4-5H3/t15-,24+,26-/m1/s1
• InChI Key: QKEDJCCCNZWOBS-SGOPFIAHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₇
• Molecular Weight: 454.50 g/mol
• Exact Mass: 454.19915329 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.58
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• KushenolI
• 99119-69-4
• DTXSID80243958
• HY-N2286
• AKOS032946014
• MS-28270
• CS-0019614
• (2R,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-((R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl)chroman-4-one
• (2R,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9822	98.22%
Caco-2	-	0.6782	67.82%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5415	54.15%
OATP2B1 inhibitior	-	0.7160	71.60%
OATP1B1 inhibitior	+	0.8348	83.48%
OATP1B3 inhibitior	+	0.8665	86.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9261	92.61%
P-glycoprotein inhibitior	+	0.7117	71.17%
P-glycoprotein substrate	-	0.5236	52.36%
CYP3A4 substrate	+	0.6629	66.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7270	72.70%
CYP3A4 inhibition	-	0.5389	53.89%
CYP2C9 inhibition	+	0.8322	83.22%
CYP2C19 inhibition	+	0.9154	91.54%
CYP2D6 inhibition	-	0.5403	54.03%
CYP1A2 inhibition	+	0.7480	74.80%
CYP2C8 inhibition	+	0.6788	67.88%
CYP inhibitory promiscuity	+	0.9065	90.65%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7269	72.69%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.7990	79.90%
Skin irritation	-	0.7605	76.05%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6501	65.01%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.8032	80.32%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6056	60.56%
Acute Oral Toxicity (c)	III	0.6472	64.72%
Estrogen receptor binding	+	0.8865	88.65%
Androgen receptor binding	+	0.5912	59.12%
Thyroid receptor binding	+	0.7006	70.06%
Glucocorticoid receptor binding	+	0.8840	88.40%
Aromatase binding	+	0.5894	58.94%
PPAR gamma	+	0.7268	72.68%
Honey bee toxicity	-	0.7280	72.80%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	96.08%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.42%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.39%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.99%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.05%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.96%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.74%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	91.53%	94.73%
CHEMBL2535	P11166	Glucose transporter	91.43%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.02%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.42%	93.99%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.32%	89.00%
CHEMBL1255126	O15151	Protein Mdm4	87.01%	90.20%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.79%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.25%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.90%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.38%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.92%	91.19%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.75%	89.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.52%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.33%	97.21%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.28%	94.03%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 20832634
• NPASS: NPC159539
• LOTUS: LTS0146603
• wikiData: Q105223047