[(1S,2S,3S,4R,7R,8S,12S,13S,14S,16R,17R)-2,12,16-triacetyloxy-8-chloro-3-hydroxy-4,13-dimethyl-9-methylidene-5-oxospiro[6-oxatricyclo[11.4.0.03,7]heptadecane-17,2'-oxirane]-14-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 91898ea9-2597-4991-89b7-dd5a471db21b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1S,2S,3S,4R,7R,8S,12S,13S,14S,16R,17R)-2,12,16-triacetyloxy-8-chloro-3-hydroxy-4,13-dimethyl-9-methylidene-5-oxospiro[6-oxatricyclo[11.4.0.03,7]heptadecane-17,2'-oxirane]-14-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C2(CO2)C3C1(C(CCC(=C)C(C4C(C3OC(=O)C)(C(C(=O)O4)C)O)Cl)OC(=O)C)C)OC(=O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1C[C@H]([C@]2(CO2)[C@H]3[C@]1([C@H](CCC(=C)[C@@H]([C@H]4[C@@]([C@H]3OC(=O)C)([C@H](C(=O)O4)C)O)Cl)OC(=O)C)C)OC(=O)C
• InChI: InChI=1S/C31H43ClO12/c1-9-14(2)27(36)43-21-12-22(41-18(6)34)30(13-39-30)24-26(42-19(7)35)31(38)16(4)28(37)44-25(31)23(32)15(3)10-11-20(29(21,24)8)40-17(5)33/h14,16,20-26,38H,3,9-13H2,1-2,4-8H3/t14-,16+,20+,21+,22-,23+,24-,25+,26+,29+,30-,31-/m1/s1
• InChI Key: LRFGSFLHFBEWPF-NEXRVXEQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₃ClO₁₂
• Molecular Weight: 643.10 g/mol
• Exact Mass: 642.2443045 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 12
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	-	0.7963	79.63%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6964	69.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8139	81.39%
OATP1B3 inhibitior	+	0.8611	86.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9364	93.64%
P-glycoprotein inhibitior	+	0.7762	77.62%
P-glycoprotein substrate	+	0.5707	57.07%
CYP3A4 substrate	+	0.7038	70.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8703	87.03%
CYP3A4 inhibition	-	0.7007	70.07%
CYP2C9 inhibition	-	0.7347	73.47%
CYP2C19 inhibition	-	0.8015	80.15%
CYP2D6 inhibition	-	0.8888	88.88%
CYP1A2 inhibition	-	0.7241	72.41%
CYP2C8 inhibition	+	0.6440	64.40%
CYP inhibitory promiscuity	-	0.8798	87.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8682	86.82%
Carcinogenicity (trinary)	Non-required	0.4399	43.99%
Eye corrosion	-	0.9827	98.27%
Eye irritation	-	0.8930	89.30%
Skin irritation	-	0.5553	55.53%
Skin corrosion	-	0.9051	90.51%
Ames mutagenesis	-	0.5637	56.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4928	49.28%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5428	54.28%
skin sensitisation	-	0.8341	83.41%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5938	59.38%
Acute Oral Toxicity (c)	III	0.5646	56.46%
Estrogen receptor binding	+	0.7924	79.24%
Androgen receptor binding	+	0.6724	67.24%
Thyroid receptor binding	+	0.5364	53.64%
Glucocorticoid receptor binding	+	0.7649	76.49%
Aromatase binding	+	0.7297	72.97%
PPAR gamma	+	0.7505	75.05%
Honey bee toxicity	-	0.6591	65.91%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.83%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.33%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.49%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	91.83%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.22%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.18%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.99%	98.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.92%	89.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.55%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.17%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.94%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.50%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.41%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.13%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.73%	94.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.74%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	82.39%	92.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.38%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.24%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.19%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.03%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.56%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	80.49%	97.79%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.41%	95.71%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.03%	89.05%

Plants that contains it

• Beta vulgaris
• Sonchus arvensis
• Sonchus macrocarpus

Cross-Links

• PubChem: 163104940
• LOTUS: LTS0200028
• wikiData: Q104195685