[5-formyl-4,8-dihydroxy-3-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] 2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 49a42fe6-8f14-4f58-a330-0f53dd50564e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [5-formyl-4,8-dihydroxy-3-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] 2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC=C(CO)C(=O)OC1CC2(C(CCC(C2C(C1C(=C)C(=O)OC)O)C=O)O)C
• SMILES (Isomeric): CC=C(CO)C(=O)OC1CC2(C(CCC(C2C(C1C(=C)C(=O)OC)O)C=O)O)C
• InChI: InChI=1S/C21H30O8/c1-5-12(9-22)20(27)29-14-8-21(3)15(24)7-6-13(10-23)17(21)18(25)16(14)11(2)19(26)28-4/h5,10,13-18,22,24-25H,2,6-9H2,1,3-4H3
• InChI Key: SJDLIJHKRINTTQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₈
• Molecular Weight: 410.50 g/mol
• Exact Mass: 410.19406791 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.54
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9818	98.18%
Caco-2	-	0.6289	62.89%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8384	83.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.8105	81.05%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.5512	55.12%
P-glycoprotein substrate	+	0.5516	55.16%
CYP3A4 substrate	+	0.6850	68.50%
CYP2C9 substrate	-	0.7952	79.52%
CYP2D6 substrate	-	0.8979	89.79%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8266	82.66%
CYP2C19 inhibition	-	0.8660	86.60%
CYP2D6 inhibition	-	0.9509	95.09%
CYP1A2 inhibition	-	0.7622	76.22%
CYP2C8 inhibition	-	0.5891	58.91%
CYP inhibitory promiscuity	-	0.9283	92.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7140	71.40%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9573	95.73%
Skin irritation	-	0.5407	54.07%
Skin corrosion	-	0.9658	96.58%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4201	42.01%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6146	61.46%
skin sensitisation	-	0.8901	89.01%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6027	60.27%
Acute Oral Toxicity (c)	III	0.5430	54.30%
Estrogen receptor binding	+	0.8023	80.23%
Androgen receptor binding	+	0.5380	53.80%
Thyroid receptor binding	+	0.5299	52.99%
Glucocorticoid receptor binding	+	0.7947	79.47%
Aromatase binding	+	0.5526	55.26%
PPAR gamma	+	0.5461	54.61%
Honey bee toxicity	-	0.7076	70.76%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9919	99.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.07%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.10%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.03%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.49%	94.45%
CHEMBL1871	P10275	Androgen Receptor	90.62%	96.43%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	90.23%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.68%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	88.86%	91.19%
CHEMBL4040	P28482	MAP kinase ERK2	86.97%	83.82%
CHEMBL204	P00734	Thrombin	86.08%	96.01%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.85%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.77%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.52%	92.88%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.33%	99.17%
CHEMBL5028	O14672	ADAM10	85.27%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.10%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.06%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.91%	91.07%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	83.31%	88.81%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.21%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.13%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.09%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.47%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.79%	97.47%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.96%	96.47%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.90%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.85%	95.89%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.82%	86.67%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.39%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.34%	95.56%

Plants that contains it

• Onopordum illyricum

Cross-Links

• PubChem: 73819268
• LOTUS: LTS0105031
• wikiData: Q105254231