6-Feruloylcatalpol

Details

• Internal ID: 9ad1662b-a9e0-44d1-993a-70daa319b308
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O[C@H]2[C@@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C25H30O13/c1-33-14-8-11(2-4-13(14)28)3-5-16(29)36-21-12-6-7-34-23(17(12)25(10-27)22(21)38-25)37-24-20(32)19(31)18(30)15(9-26)35-24/h2-8,12,15,17-24,26-28,30-32H,9-10H2,1H3/b5-3+/t12-,15-,17-,18-,19+,20-,21+,22+,23+,24+,25-/m1/s1
• InChI Key: RMSKZOXJAHOIER-GGKKSNITSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₃
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.16864101 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.61
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• Picroside III
• 770721-33-0
• 64461-95-6
• 6-O-feruloylcatalpol
• CHEBI:69800
• 6-O-trans-Feruloylcatalpol
• [(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 6-O-E-Feruloylcatalpol
• MEGxp0_001245
• CHEMBL2332349
• ACon1_001535
• DTXSID001346770
• AKOS032948187
• NCGC00180405-01
• NCGC00180405-03
• AC-34418
• E88807
• Q-100737
• Q27138141
• [(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6435	64.35%
Caco-2	-	0.9130	91.30%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5653	56.53%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8276	82.76%
OATP1B3 inhibitior	+	0.9676	96.76%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5448	54.48%
P-glycoprotein inhibitior	-	0.6106	61.06%
P-glycoprotein substrate	-	0.5715	57.15%
CYP3A4 substrate	+	0.6806	68.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8609	86.09%
CYP3A4 inhibition	-	0.8901	89.01%
CYP2C9 inhibition	-	0.8604	86.04%
CYP2C19 inhibition	-	0.7030	70.30%
CYP2D6 inhibition	-	0.8722	87.22%
CYP1A2 inhibition	-	0.8509	85.09%
CYP2C8 inhibition	+	0.7053	70.53%
CYP inhibitory promiscuity	-	0.7046	70.46%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5543	55.43%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9449	94.49%
Skin irritation	-	0.7812	78.12%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6446	64.46%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.7891	78.91%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8359	83.59%
Acute Oral Toxicity (c)	III	0.5594	55.94%
Estrogen receptor binding	+	0.6974	69.74%
Androgen receptor binding	-	0.4873	48.73%
Thyroid receptor binding	+	0.5590	55.90%
Glucocorticoid receptor binding	+	0.5724	57.24%
Aromatase binding	+	0.5386	53.86%
PPAR gamma	+	0.7465	74.65%
Honey bee toxicity	-	0.7495	74.95%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.6878	68.78%

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	99.78%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.36%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.44%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.35%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.80%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.51%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.26%	85.14%
CHEMBL3194	P02766	Transthyretin	90.01%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.50%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.42%	94.45%
CHEMBL4208	P20618	Proteasome component C5	88.00%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.86%	96.21%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.60%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	85.46%	94.73%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.35%	94.08%
CHEMBL1951	P21397	Monoamine oxidase A	82.11%	91.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.82%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.54%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.04%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.78%	86.92%

Plants that contains it

• Catalpa ovata
• Gentiana kurroo
• Neopicrorhiza scrophulariiflora
• Panax quinquefolius
• Scutellaria albida
• Veronica lavaudiana
• Veronica pulvinaris

Cross-Links

• PubChem: 24121289
• NPASS: NPC229548
• LOTUS: LTS0117164
• wikiData: Q27138141