Cimicifugic acid C

Details

• Internal ID: b01847b2-7517-458e-aa67-effbc547b867
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OC(C(=O)O)C(CC2=CC(=C(C=C2)O)O)(C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)O[C@H](C(=O)O)[C@](CC2=CC(=C(C=C2)O)O)(C(=O)O)O)O
• InChI: InChI=1S/C20H18O10/c21-13-5-1-11(2-6-13)4-8-16(24)30-17(18(25)26)20(29,19(27)28)10-12-3-7-14(22)15(23)9-12/h1-9,17,21-23,29H,10H2,(H,25,26)(H,27,28)/b8-4+/t17-,20-/m1/s1
• InChI Key: NIDSBIYSGNHVDL-ZUVWSUMTSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₁₀
• Molecular Weight: 418.30 g/mol
• Exact Mass: 418.08999677 g/mol
• Topological Polar Surface Area (TPSA): 182.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.87
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• 205114-67-6
• (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
• Butanedioic acid, 2-((3,4-dihydroxyphenyl)methyl)-2-hydroxy-3-(((2E)-3-(4-hydroxyphenyl)-1-2-propenyl)oxy)-, (2R,3S)-
• Butanedioic acid, 2-((3,4-dihydroxyphenyl)methyl)-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (S-(R*,S*-(E)))-
• CHEMBL1095595

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7918	79.18%
Caco-2	-	0.9247	92.47%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6306	63.06%
OATP2B1 inhibitior	-	0.5665	56.65%
OATP1B1 inhibitior	+	0.9099	90.99%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.8088	80.88%
BSEP inhibitior	+	0.7515	75.15%
P-glycoprotein inhibitior	-	0.6813	68.13%
P-glycoprotein substrate	-	0.8319	83.19%
CYP3A4 substrate	+	0.5083	50.83%
CYP2C9 substrate	-	0.5984	59.84%
CYP2D6 substrate	-	0.8616	86.16%
CYP3A4 inhibition	-	0.7683	76.83%
CYP2C9 inhibition	-	0.9156	91.56%
CYP2C19 inhibition	-	0.9363	93.63%
CYP2D6 inhibition	-	0.9314	93.14%
CYP1A2 inhibition	-	0.9000	90.00%
CYP2C8 inhibition	+	0.6407	64.07%
CYP inhibitory promiscuity	-	0.9243	92.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8775	87.75%
Carcinogenicity (trinary)	Non-required	0.6309	63.09%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.6474	64.74%
Skin irritation	-	0.7139	71.39%
Skin corrosion	-	0.9004	90.04%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4430	44.30%
Micronuclear	+	0.6577	65.77%
Hepatotoxicity	-	0.6748	67.48%
skin sensitisation	-	0.5798	57.98%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8264	82.64%
Acute Oral Toxicity (c)	III	0.8128	81.28%
Estrogen receptor binding	+	0.8211	82.11%
Androgen receptor binding	+	0.8294	82.94%
Thyroid receptor binding	+	0.5412	54.12%
Glucocorticoid receptor binding	+	0.7302	73.02%
Aromatase binding	+	0.5229	52.29%
PPAR gamma	+	0.6532	65.32%
Honey bee toxicity	-	0.7933	79.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9880	98.80%

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	97.72%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.78%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.59%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.58%	98.95%
CHEMBL3194	P02766	Transthyretin	92.19%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.88%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.64%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.14%	95.50%
CHEMBL1951	P21397	Monoamine oxidase A	90.08%	91.49%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	89.81%	80.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.23%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.80%	99.15%
CHEMBL4040	P28482	MAP kinase ERK2	86.74%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.87%	96.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.82%	91.71%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	83.30%	96.09%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.60%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.29%	89.00%
CHEMBL2535	P11166	Glucose transporter	81.04%	98.75%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	80.68%	92.29%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.48%	97.53%
CHEMBL3401	O75469	Pregnane X receptor	80.43%	94.73%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.32%	94.97%

Plants that contains it

• Actaea dahurica
• Actaea simplex

Cross-Links

• PubChem: 6450178
• NPASS: NPC156709
• LOTUS: LTS0032007
• wikiData: Q104389568