(2S)-2-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-hydroxy-4-methoxyphenyl]-5-hydroxy-7-methoxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 8c66974e-5e01-43ed-9eb7-f5f397fa3d26
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 2-prenylated flavans > 2-prenylated flavanones
• IUPAC Name: (2S)-2-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-hydroxy-4-methoxyphenyl]-5-hydroxy-7-methoxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C=CC(=C1O)OC)C2CC(=O)C3=C(C=C(C=C3O2)OC)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C=CC(=C1O)OC)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)OC)O)/C)C
• InChI: InChI=1S/C27H32O6/c1-16(2)7-6-8-17(3)9-10-20-19(11-12-23(32-5)27(20)30)24-15-22(29)26-21(28)13-18(31-4)14-25(26)33-24/h7,9,11-14,24,28,30H,6,8,10,15H2,1-5H3/b17-9+/t24-/m0/s1
• InChI Key: KCIUHPNLNSGZBY-CKRLVEJWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₆
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.21988874 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.06
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9828	98.28%
Caco-2	+	0.5287	52.87%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7855	78.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8877	88.77%
OATP1B3 inhibitior	+	0.8673	86.73%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7814	78.14%
BSEP inhibitior	+	0.9704	97.04%
P-glycoprotein inhibitior	+	0.8634	86.34%
P-glycoprotein substrate	-	0.6408	64.08%
CYP3A4 substrate	+	0.6466	64.66%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	-	0.6719	67.19%
CYP2C9 inhibition	-	0.5205	52.05%
CYP2C19 inhibition	+	0.6916	69.16%
CYP2D6 inhibition	-	0.7396	73.96%
CYP1A2 inhibition	+	0.8250	82.50%
CYP2C8 inhibition	+	0.6793	67.93%
CYP inhibitory promiscuity	+	0.6349	63.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7474	74.74%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.8412	84.12%
Skin irritation	-	0.7876	78.76%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6788	67.88%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8437	84.37%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5885	58.85%
Acute Oral Toxicity (c)	III	0.3469	34.69%
Estrogen receptor binding	+	0.8448	84.48%
Androgen receptor binding	+	0.6408	64.08%
Thyroid receptor binding	+	0.5595	55.95%
Glucocorticoid receptor binding	+	0.8452	84.52%
Aromatase binding	+	0.6065	60.65%
PPAR gamma	+	0.8232	82.32%
Honey bee toxicity	-	0.7511	75.11%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9964	99.64%

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	99.17%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.94%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.54%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.36%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.96%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.92%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.50%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.40%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.27%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.29%	99.23%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	89.13%	92.68%
CHEMBL3401	O75469	Pregnane X receptor	88.77%	94.73%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.61%	96.12%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	88.53%	92.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.15%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.71%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.60%	91.07%
CHEMBL2535	P11166	Glucose transporter	85.54%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.39%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.34%	90.71%
CHEMBL4208	P20618	Proteasome component C5	83.54%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.38%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	81.30%	91.19%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.86%	83.10%

Plants that contains it

• Bobgunnia madagascariensis
• Calodendrum capense
• Croton caudatus
• Elaeocarpus fuscoides
• Jacobaea adonidifolia
• Macaranga tanarius
• Meconopsis horridula
• Oxera splendida
• Stevia eupatoria
• Vitex pinnata

Cross-Links

• PubChem: 11351463
• NPASS: NPC21210
• LOTUS: LTS0022721
• wikiData: Q105138764