(5R,6E)-5-Hydroxy-7-phenyl-2,6-heptadienoic acid methyl ester

Details

• Internal ID: 0099ce58-28dd-4d85-a1d0-0db2c7805ec1
• Taxonomy: Phenylpropanoids and polyketides > Cinnamyl alcohols
• IUPAC Name: methyl (2E,5R,6E)-5-hydroxy-7-phenylhepta-2,6-dienoate
• SMILES (Canonical): COC(=O)C=CCC(C=CC1=CC=CC=C1)O
• SMILES (Isomeric): COC(=O)/C=C/C[C@H](/C=C/C1=CC=CC=C1)O
• InChI: InChI=1S/C14H16O3/c1-17-14(16)9-5-8-13(15)11-10-12-6-3-2-4-7-12/h2-7,9-11,13,15H,8H2,1H3/b9-5+,11-10+/t13-/m1/s1
• InChI Key: VUILPHNRZJUSCY-LYITZRKNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₃
• Molecular Weight: 232.27 g/mol
• Exact Mass: 232.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.9109	91.09%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7335	73.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9032	90.32%
OATP1B3 inhibitior	+	0.9639	96.39%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6835	68.35%
P-glycoprotein inhibitior	-	0.9511	95.11%
P-glycoprotein substrate	-	0.9395	93.95%
CYP3A4 substrate	-	0.5838	58.38%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.8567	85.67%
CYP3A4 inhibition	-	0.9730	97.30%
CYP2C9 inhibition	-	0.9756	97.56%
CYP2C19 inhibition	-	0.9267	92.67%
CYP2D6 inhibition	-	0.9660	96.60%
CYP1A2 inhibition	-	0.8353	83.53%
CYP2C8 inhibition	+	0.4790	47.90%
CYP inhibitory promiscuity	-	0.9086	90.86%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.6023	60.23%
Carcinogenicity (trinary)	Non-required	0.7356	73.56%
Eye corrosion	-	0.7867	78.67%
Eye irritation	-	0.6200	62.00%
Skin irritation	+	0.7004	70.04%
Skin corrosion	-	0.8479	84.79%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7016	70.16%
Micronuclear	-	0.7179	71.79%
Hepatotoxicity	-	0.5227	52.27%
skin sensitisation	+	0.6593	65.93%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	-	0.8226	82.26%
Acute Oral Toxicity (c)	III	0.7287	72.87%
Estrogen receptor binding	+	0.6654	66.54%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.8312	83.12%
Glucocorticoid receptor binding	+	0.5657	56.57%
Aromatase binding	-	0.5061	50.61%
PPAR gamma	-	0.7126	71.26%
Honey bee toxicity	-	0.9453	94.53%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.6432	64.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.15%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.52%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.41%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.99%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	92.86%	90.17%
CHEMBL2581	P07339	Cathepsin D	92.83%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.59%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.46%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.25%	94.73%
CHEMBL5028	O14672	ADAM10	84.11%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.32%	95.50%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.79%	100.00%

Plants that contains it

• Mortonia palmeri

Cross-Links

• PubChem: 101453962
• NPASS: NPC277921