[(2S)-2-[(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-15-oxo-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-5-yl]propyl] acetate

Details

• Internal ID: de8afa09-de50-4179-b31b-672b35b6537b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(2S)-2-[(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-15-oxo-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-5-yl]propyl] acetate
• SMILES (Canonical): CC(COC(=O)C)C1=C(C(=C2C(=C1)C3CC4C2(CCCC4(C)C)C(=O)O3)O)O
• SMILES (Isomeric): C[C@H](COC(=O)C)C1=C(C(=C2C(=C1)[C@@H]3C[C@@H]4[C@@]2(CCCC4(C)C)C(=O)O3)O)O
• InChI: InChI=1S/C22H28O6/c1-11(10-27-12(2)23)13-8-14-15-9-16-21(3,4)6-5-7-22(16,20(26)28-15)17(14)19(25)18(13)24/h8,11,15-16,24-25H,5-7,9-10H2,1-4H3/t11-,15+,16+,22-/m1/s1
• InChI Key: LEGUIGFYWUCHAY-VXQXEOLMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₆
• Molecular Weight: 388.50 g/mol
• Exact Mass: 388.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.83
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8508	85.08%
Caco-2	-	0.6059	60.59%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.9179	91.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8154	81.54%
OATP1B3 inhibitior	+	0.8639	86.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7834	78.34%
P-glycoprotein inhibitior	-	0.7077	70.77%
P-glycoprotein substrate	-	0.6974	69.74%
CYP3A4 substrate	+	0.6718	67.18%
CYP2C9 substrate	-	0.5858	58.58%
CYP2D6 substrate	-	0.8130	81.30%
CYP3A4 inhibition	-	0.8040	80.40%
CYP2C9 inhibition	-	0.7903	79.03%
CYP2C19 inhibition	-	0.7625	76.25%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	+	0.6081	60.81%
CYP2C8 inhibition	-	0.6268	62.68%
CYP inhibitory promiscuity	-	0.9003	90.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7261	72.61%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8922	89.22%
Skin irritation	-	0.7802	78.02%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8468	84.68%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5059	50.59%
skin sensitisation	-	0.9178	91.78%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7506	75.06%
Acute Oral Toxicity (c)	III	0.5824	58.24%
Estrogen receptor binding	+	0.7956	79.56%
Androgen receptor binding	+	0.6796	67.96%
Thyroid receptor binding	+	0.6483	64.83%
Glucocorticoid receptor binding	+	0.8595	85.95%
Aromatase binding	+	0.5881	58.81%
PPAR gamma	+	0.7022	70.22%
Honey bee toxicity	-	0.8100	81.00%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	99.26%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.94%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.33%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.20%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.71%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.96%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.86%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.31%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.38%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.14%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	87.23%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.77%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.74%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.43%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.40%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.39%	92.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.20%	89.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.84%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.80%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.07%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.38%	93.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.25%	89.67%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.16%	93.04%

Plants that contains it

• Salvia canariensis

Cross-Links

• PubChem: 162844585
• LOTUS: LTS0097483
• wikiData: Q105150558