3-[(3S)-5-[(6aR,7R,8S,9R,10aS)-9-hydroxy-7,8-dimethyl-3-oxo-5,6,6a,8,9,10-hexahydro-1H-benzo[d][2]benzofuran-7-yl]-3-methylpentoxy]-3-oxopropanoic acid

Details

• Internal ID: 171b3760-5812-4fe7-83c7-695e14f094a9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 3-[(3S)-5-[(6aR,7R,8S,9R,10aS)-9-hydroxy-7,8-dimethyl-3-oxo-5,6,6a,8,9,10-hexahydro-1H-benzo[d][2]benzofuran-7-yl]-3-methylpentoxy]-3-oxopropanoic acid
• SMILES (Canonical): CC1C(CC23COC(=O)C2=CCCC3C1(C)CCC(C)CCOC(=O)CC(=O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H](C[C@@]23COC(=O)C2=CCC[C@@H]3[C@@]1(C)CC[C@H](C)CCOC(=O)CC(=O)O)O
• InChI: InChI=1S/C23H34O7/c1-14(8-10-29-20(27)11-19(25)26)7-9-22(3)15(2)17(24)12-23-13-30-21(28)16(23)5-4-6-18(22)23/h5,14-15,17-18,24H,4,6-13H2,1-3H3,(H,25,26)/t14-,15+,17+,18+,22-,23+/m0/s1
• InChI Key: CCAVMGBTZLRHDV-GWPPXWQZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₇
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.23045342 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9786	97.86%
Caco-2	-	0.5699	56.99%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8263	82.63%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.8968	89.68%
OATP1B3 inhibitior	+	0.9707	97.07%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5271	52.71%
BSEP inhibitior	+	0.7162	71.62%
P-glycoprotein inhibitior	+	0.5917	59.17%
P-glycoprotein substrate	+	0.5468	54.68%
CYP3A4 substrate	+	0.6717	67.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9031	90.31%
CYP3A4 inhibition	-	0.6290	62.90%
CYP2C9 inhibition	-	0.8923	89.23%
CYP2C19 inhibition	-	0.9269	92.69%
CYP2D6 inhibition	-	0.9349	93.49%
CYP1A2 inhibition	-	0.7504	75.04%
CYP2C8 inhibition	-	0.6526	65.26%
CYP inhibitory promiscuity	-	0.8700	87.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4358	43.58%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9470	94.70%
Skin irritation	+	0.6498	64.98%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.7178	71.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6584	65.84%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5241	52.41%
skin sensitisation	-	0.9157	91.57%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5648	56.48%
Acute Oral Toxicity (c)	III	0.5493	54.93%
Estrogen receptor binding	+	0.8093	80.93%
Androgen receptor binding	+	0.5523	55.23%
Thyroid receptor binding	+	0.6573	65.73%
Glucocorticoid receptor binding	+	0.8420	84.20%
Aromatase binding	+	0.7721	77.21%
PPAR gamma	-	0.4892	48.92%
Honey bee toxicity	-	0.8696	86.96%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9913	99.13%

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	98.42%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.93%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.04%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.60%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.33%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.61%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.33%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.22%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.00%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	85.15%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.13%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.02%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.90%	90.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.88%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.45%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.71%	100.00%
CHEMBL5028	O14672	ADAM10	81.69%	97.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.35%	93.03%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.16%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.29%	96.00%

Plants that contains it

• Olearia teretifolia

Cross-Links

• PubChem: 162865524
• LOTUS: LTS0017370
• wikiData: Q104953035