[(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,17S)-2,12-diacetyloxy-8-chloro-3-hydroxy-4,13-dimethyl-9-methylidene-5-oxospiro[6-oxatricyclo[11.4.0.03,7]heptadec-10-ene-17,2'-oxirane]-14-yl] acetate

Details

• Internal ID: 21b0e752-8a48-49aa-968e-4f805737fe2b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,17S)-2,12-diacetyloxy-8-chloro-3-hydroxy-4,13-dimethyl-9-methylidene-5-oxospiro[6-oxatricyclo[11.4.0.03,7]heptadec-10-ene-17,2'-oxirane]-14-yl] acetate
• SMILES (Canonical): CC1C(=O)OC2C1(C(C3C(C(CCC34CO4)OC(=O)C)(C(C=CC(=C)C2Cl)OC(=O)C)C)OC(=O)C)O
• SMILES (Isomeric): C[C@H]1C(=O)O[C@@H]2[C@@]1([C@H]([C@@H]3[C@]([C@H](CC[C@@]34CO4)OC(=O)C)([C@H](/C=C\C(=C)[C@@H]2Cl)OC(=O)C)C)OC(=O)C)O
• InChI: InChI=1S/C26H33ClO10/c1-12-7-8-17(34-14(3)28)24(6)18(35-15(4)29)9-10-25(11-33-25)20(24)22(36-16(5)30)26(32)13(2)23(31)37-21(26)19(12)27/h7-8,13,17-22,32H,1,9-11H2,2-6H3/b8-7-/t13-,17-,18-,19-,20+,21-,22-,24-,25+,26-/m0/s1
• InChI Key: GTHKEJRKRGQZPU-PCNNKYCXSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₃ClO₁₀
• Molecular Weight: 541.00 g/mol
• Exact Mass: 540.1762249 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	-	0.7385	73.85%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7608	76.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8280	82.80%
OATP1B3 inhibitior	+	0.8924	89.24%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7678	76.78%
P-glycoprotein inhibitior	+	0.7432	74.32%
P-glycoprotein substrate	-	0.5458	54.58%
CYP3A4 substrate	+	0.7046	70.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8818	88.18%
CYP3A4 inhibition	-	0.8996	89.96%
CYP2C9 inhibition	-	0.8051	80.51%
CYP2C19 inhibition	-	0.8438	84.38%
CYP2D6 inhibition	-	0.9157	91.57%
CYP1A2 inhibition	-	0.6814	68.14%
CYP2C8 inhibition	+	0.5376	53.76%
CYP inhibitory promiscuity	-	0.9404	94.04%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8782	87.82%
Carcinogenicity (trinary)	Non-required	0.4353	43.53%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.9221	92.21%
Skin irritation	-	0.6177	61.77%
Skin corrosion	-	0.8928	89.28%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6728	67.28%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5019	50.19%
skin sensitisation	-	0.7935	79.35%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.8424	84.24%
Acute Oral Toxicity (c)	III	0.5507	55.07%
Estrogen receptor binding	+	0.8177	81.77%
Androgen receptor binding	+	0.6611	66.11%
Thyroid receptor binding	+	0.5847	58.47%
Glucocorticoid receptor binding	+	0.7718	77.18%
Aromatase binding	+	0.6599	65.99%
PPAR gamma	+	0.7542	75.42%
Honey bee toxicity	-	0.6096	60.96%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	95.63%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.37%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.82%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.51%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.79%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.63%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.68%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.85%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.41%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.40%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.04%	94.80%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.92%	97.14%
CHEMBL1937	Q92769	Histone deacetylase 2	84.58%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.00%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.37%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.28%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.19%	97.09%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.33%	94.42%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.29%	94.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.04%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.29%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.22%	92.94%

Plants that contains it

• Anisomeles indica

Cross-Links

• PubChem: 11786042
• NPASS: NPC79012