(1S,4aS,6S,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxyoxan-2-yl]oxy-6-hydroxy-7-methylidene-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 84bcae2a-ba1d-4bcd-8012-93fc75d6d8af
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (1S,4aS,6S,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxyoxan-2-yl]oxy-6-hydroxy-7-methylidene-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): C=C1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)OC(=O)C5=CC=C(C=C5)O)O
• SMILES (Isomeric): C=C1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)OC(=O)C5=CC=C(C=C5)O)O
• InChI: InChI=1S/C32H32O15/c1-14-21(35)11-18-19(29(40)41)12-44-31(25(14)18)47-32-28(46-30(42)16-4-6-17(33)7-5-16)27(39)26(38)23(45-32)13-43-24(37)9-3-15-2-8-20(34)22(36)10-15/h2-10,12,18,21,23,25-28,31-36,38-39H,1,11,13H2,(H,40,41)/b9-3+/t18-,21+,23-,25-,26-,27+,28-,31+,32+/m1/s1
• InChI Key: HCERMAQLPHPTQE-PTWHRHFTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₂O₁₅
• Molecular Weight: 656.60 g/mol
• Exact Mass: 656.17412031 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8314	83.14%
Caco-2	-	0.9003	90.03%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6781	67.81%
OATP2B1 inhibitior	-	0.7154	71.54%
OATP1B1 inhibitior	+	0.7872	78.72%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6024	60.24%
P-glycoprotein inhibitior	+	0.6340	63.40%
P-glycoprotein substrate	-	0.5079	50.79%
CYP3A4 substrate	+	0.6799	67.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8667	86.67%
CYP3A4 inhibition	-	0.7741	77.41%
CYP2C9 inhibition	-	0.5507	55.07%
CYP2C19 inhibition	-	0.5194	51.94%
CYP2D6 inhibition	-	0.8020	80.20%
CYP1A2 inhibition	-	0.7061	70.61%
CYP2C8 inhibition	+	0.8468	84.68%
CYP inhibitory promiscuity	-	0.8270	82.70%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6690	66.90%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9016	90.16%
Skin irritation	-	0.7740	77.40%
Skin corrosion	-	0.9412	94.12%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3770	37.70%
Micronuclear	+	0.6692	66.92%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7315	73.15%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8519	85.19%
Acute Oral Toxicity (c)	III	0.3955	39.55%
Estrogen receptor binding	+	0.8017	80.17%
Androgen receptor binding	+	0.7262	72.62%
Thyroid receptor binding	+	0.5632	56.32%
Glucocorticoid receptor binding	+	0.6018	60.18%
Aromatase binding	+	0.5438	54.38%
PPAR gamma	+	0.6939	69.39%
Honey bee toxicity	-	0.6985	69.85%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9856	98.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.97%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.01%	91.11%
CHEMBL3194	P02766	Transthyretin	98.01%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.94%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.75%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.50%	97.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	94.28%	85.31%
CHEMBL4208	P20618	Proteasome component C5	93.96%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.60%	99.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.09%	97.21%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.96%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	89.76%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	89.36%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.71%	96.95%
CHEMBL206	P03372	Estrogen receptor alpha	88.48%	97.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.10%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.02%	83.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.91%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.88%	96.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.62%	80.78%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	86.46%	97.53%
CHEMBL5255	O00206	Toll-like receptor 4	86.15%	92.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.39%	89.62%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.70%	95.64%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.83%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	82.54%	95.93%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	81.97%	97.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.83%	100.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.66%	91.71%
CHEMBL3401	O75469	Pregnane X receptor	80.55%	94.73%

Plants that contains it

• Vitex altissima

Cross-Links

• PubChem: 11787128
• LOTUS: LTS0215074
• wikiData: Q105025645