(2R)-2-[(1E,4S,6R,8R,9E)-4,6,8-trihydroxy-10-phenyldeca-1,9-dienyl]-2,3-dihydropyran-6-one

Details

• Internal ID: 845c85e4-9d19-47c7-a41f-8c6439ce8eeb
• Taxonomy: Phenylpropanoids and polyketides > Cinnamyl alcohols
• IUPAC Name: (2R)-2-[(1E,4S,6R,8R,9E)-4,6,8-trihydroxy-10-phenyldeca-1,9-dienyl]-2,3-dihydropyran-6-one
• SMILES (Canonical): C1C=CC(=O)OC1C=CCC(CC(CC(C=CC2=CC=CC=C2)O)O)O
• SMILES (Isomeric): C1C=CC(=O)O[C@H]1/C=C/C[C@@H](C[C@H](C[C@H](/C=C/C2=CC=CC=C2)O)O)O
• InChI: InChI=1S/C21H26O5/c22-17(8-4-9-20-10-5-11-21(25)26-20)14-19(24)15-18(23)13-12-16-6-2-1-3-7-16/h1-7,9,11-13,17-20,22-24H,8,10,14-15H2/b9-4+,13-12+/t17-,18-,19+,20-/m0/s1
• InChI Key: HDJDRGQCGAWPGK-KUSHCJQLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.17802393 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7590	75.90%
Caco-2	-	0.7529	75.29%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6755	67.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8548	85.48%
OATP1B3 inhibitior	+	0.9565	95.65%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5930	59.30%
P-glycoprotein inhibitior	-	0.6167	61.67%
P-glycoprotein substrate	-	0.7010	70.10%
CYP3A4 substrate	+	0.5489	54.89%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	+	0.6814	68.14%
CYP2C9 inhibition	-	0.8599	85.99%
CYP2C19 inhibition	-	0.7358	73.58%
CYP2D6 inhibition	-	0.9168	91.68%
CYP1A2 inhibition	-	0.9399	93.99%
CYP2C8 inhibition	-	0.5874	58.74%
CYP inhibitory promiscuity	-	0.7570	75.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8828	88.28%
Carcinogenicity (trinary)	Non-required	0.6518	65.18%
Eye corrosion	-	0.9796	97.96%
Eye irritation	-	0.8756	87.56%
Skin irritation	-	0.6014	60.14%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4054	40.54%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7825	78.25%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8256	82.56%
Acute Oral Toxicity (c)	III	0.6036	60.36%
Estrogen receptor binding	+	0.8124	81.24%
Androgen receptor binding	+	0.6472	64.72%
Thyroid receptor binding	-	0.5782	57.82%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6401	64.01%
PPAR gamma	+	0.7728	77.28%
Honey bee toxicity	-	0.8647	86.47%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7195	71.95%

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	96.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.80%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.98%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.05%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.61%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.91%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.10%	93.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.04%	94.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.16%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.23%	100.00%

Plants that contains it

• Cryptocarya moschata

Cross-Links

• PubChem: 101052043
• LOTUS: LTS0027163
• wikiData: Q105026379