Fukinolic acid

Details

• Internal ID: b6518251-a31f-4f36-ac4d-276756e161e4
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-2-hydroxybutanedioic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)(C(=O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@@]([C@@H](C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)(C(=O)O)O)O)O
• InChI: InChI=1S/C20H18O11/c21-12-4-1-10(7-14(12)23)3-6-16(25)31-17(18(26)27)20(30,19(28)29)9-11-2-5-13(22)15(24)8-11/h1-8,17,21-24,30H,9H2,(H,26,27)(H,28,29)/b6-3+/t17-,20-/m1/s1
• InChI Key: ACYXDIZTQDLTCB-UVIKLTKHSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₁₁
• Molecular Weight: 434.30 g/mol
• Exact Mass: 434.08491139 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.58
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 50982-40-6
• UNII-OLL8DU5J30
• OLL8DU5J30
• (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-2-hydroxybutanedioic acid
• Butanedioic acid, 2-((3,4-dihydroxyphenyl)methyl)-3-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-2-hydroxy-, (2R,3S)-
• (2R,3S)-2-(3,4-Dihydroxybenzyl)-3-(((2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl)oxy)-2-hydroxysuccinic acid
• BUTANEDIOIC ACID, 2-((3,4-DIHYDROXYPHENYL)METHYL)-3-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-2-HYDROXY-, (2R,3S)-
• BUTANEDIOIC ACID, 2-((3,4-DIHYDROXYPHENYL)METHYL)-3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-2-HYDROXY-, (S-(R*,S*-(E)))-
• CHEMBL487192
• MEGxp0_000157
• SCHEMBL18371556
• ACon1_000044
• CHEBI:177596
• DTXSID401317189
• NCGC00168846-01
• Q27285721
• NCGC00168846-02!(2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-2-hydroxybutanedioic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7918	79.18%
Caco-2	-	0.9307	93.07%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6306	63.06%
OATP2B1 inhibitior	-	0.5623	56.23%
OATP1B1 inhibitior	+	0.9220	92.20%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.8088	80.88%
BSEP inhibitior	+	0.8398	83.98%
P-glycoprotein inhibitior	-	0.6289	62.89%
P-glycoprotein substrate	-	0.8737	87.37%
CYP3A4 substrate	-	0.5239	52.39%
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	+	0.4699	46.99%
CYP inhibitory promiscuity	-	0.9243	92.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8775	87.75%
Carcinogenicity (trinary)	Non-required	0.6309	63.09%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.7051	70.51%
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	-	0.4448	44.48%
Micronuclear	+	0.6577	65.77%
Hepatotoxicity	-	0.5426	54.26%
skin sensitisation	-	0.5798	57.98%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8959	89.59%
Acute Oral Toxicity (c)	III	0.8128	81.28%
Estrogen receptor binding	+	0.8652	86.52%
Androgen receptor binding	+	0.8031	80.31%
Thyroid receptor binding	+	0.5914	59.14%
Glucocorticoid receptor binding	+	0.7354	73.54%
Aromatase binding	+	0.5663	56.63%
PPAR gamma	+	0.6733	67.33%
Honey bee toxicity	-	0.8323	83.23%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
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	98.32%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.82%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.79%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.31%	99.17%
CHEMBL2581	P07339	Cathepsin D	93.37%	98.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	92.11%	80.78%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.93%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.64%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.27%	96.00%
CHEMBL3194	P02766	Transthyretin	89.64%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.60%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.91%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.23%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.27%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	81.39%	94.73%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.32%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	81.03%	83.82%

Plants that contains it

• Acacia paradoxa
• Actaea cimicifuga
• Actaea dahurica
• Actaea racemosa
• Actaea simplex
• Adonis sutchuenensis
• Astragalus ernestii
• Berneuxia thibetica
• Bongardia chrysogonum
• Eragrostis curvula
• Fritillaria meleagris
• Isophysis tasmanica
• Matricaria discoidea
• Metasequoia glyptostroboides
• Petasites japonicus
• Philenoptera laxiflora
• Plantago lundborgii
• Sideritis arborescens
• Solanum pseudoquina
• Triadica sebifera

Cross-Links

• PubChem: 6441059
• NPASS: NPC179505
• ChEMBL: CHEMBL487192
• LOTUS: LTS0045840
• wikiData: Q27285721