Cimicifugic acid E

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	9e5e0f11-7048-4a9e-b050-e8266cf007f6
Taxonomy	Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name	(2R,3S)-2-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid
SMILES (Canonical)	COC1=C(C=CC(=C1)C=CC(=O)OC(C(=O)O)C(CC2=CC=C(C=C2)O)(C(=O)O)O)O
SMILES (Isomeric)	COC1=C(C=CC(=C1)/C=C/C(=O)O[C@H](C(=O)O)[C@](CC2=CC=C(C=C2)O)(C(=O)O)O)O
InChI	InChI=1S/C21H20O10/c1-30-16-10-12(4-8-15(16)23)5-9-17(24)31-18(19(25)26)21(29,20(27)28)11-13-2-6-14(22)7-3-13/h2-10,18,22-23,29H,11H2,1H3,(H,25,26)(H,27,28)/b9-5+/t18-,21-/m1/s1
InChI Key	CAIGUMKGQLGFBR-PZTMCFHLSA-N
Popularity	2 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₁H₂₀O₁₀
Molecular Weight	432.40 g/mol
Exact Mass	432.10564683 g/mol
Topological Polar Surface Area (TPSA)	171.00 Å²
XlogP	1.80
Atomic LogP (AlogP)	1.17
H-Bond Acceptor	8
H-Bond Donor	5
Rotatable Bonds	9

Synonyms

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2-E-Feruloylpiscidic acid

R8K7J9Q7VA

UNII-R8K7J9Q7VA

219986-67-1

CIMICIFUGIC ACID E, (+)-

Butanedioic acid, 2-hydroxy-3-(((2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl)oxy)-2-((4-hydroxyphenyl)methyl)-, (2R,3S)-

(2R,3S)-2-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

BUTANEDIOIC ACID, 2-HYDROXY-3-(((2E)-3-(4-HYDROXY-3-METHOXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-2-((4-HYDROXYPHENYL)METHYL)-, (2R,3S)-

CHEMBL1095920

Q27287973

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8331	83.31%
Caco-2	-	0.8891	88.91%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6473	64.73%
OATP2B1 inhibitior	+	0.5677	56.77%
OATP1B1 inhibitior	+	0.8907	89.07%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7588	75.88%
BSEP inhibitior	+	0.8868	88.68%
P-glycoprotein inhibitior	-	0.5566	55.66%
P-glycoprotein substrate	-	0.6929	69.29%
CYP3A4 substrate	+	0.5548	55.48%
CYP2C9 substrate	-	0.5984	59.84%
CYP2D6 substrate	-	0.8478	84.78%
CYP3A4 inhibition	-	0.7866	78.66%
CYP2C9 inhibition	-	0.8579	85.79%
CYP2C19 inhibition	-	0.8984	89.84%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	-	0.8001	80.01%
CYP2C8 inhibition	+	0.8139	81.39%
CYP inhibitory promiscuity	-	0.9272	92.72%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8775	87.75%
Carcinogenicity (trinary)	Non-required	0.6469	64.69%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8191	81.91%
Skin irritation	-	0.7373	73.73%
Skin corrosion	-	0.8666	86.66%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5256	52.56%
Micronuclear	+	0.6577	65.77%
Hepatotoxicity	-	0.7801	78.01%
skin sensitisation	-	0.7693	76.93%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9117	91.17%
Acute Oral Toxicity (c)	III	0.7563	75.63%
Estrogen receptor binding	+	0.8148	81.48%
Androgen receptor binding	+	0.7510	75.10%
Thyroid receptor binding	+	0.5658	56.58%
Glucocorticoid receptor binding	+	0.7210	72.10%
Aromatase binding	+	0.5246	52.46%
PPAR gamma	+	0.6387	63.87%
Honey bee toxicity	-	0.8425	84.25%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9769	97.69%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	97.29%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.03%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.68%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.43%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.02%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.65%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	92.57%	90.20%
CHEMBL2581	P07339	Cathepsin D	91.99%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.95%	94.45%
CHEMBL3194	P02766	Transthyretin	89.72%	90.71%
CHEMBL2535	P11166	Glucose transporter	89.48%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.98%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.37%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.53%	89.62%
CHEMBL4040	P28482	MAP kinase ERK2	81.52%	83.82%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.38%	91.71%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	81.35%	92.29%
CHEMBL3401	O75469	Pregnane X receptor	80.71%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.41%	90.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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