[(1S,2S,3aR,5R,6Z,9S,10S,11S,13R,13aS)-10-acetyloxy-1-(3-hydroperoxy-2-methylidenebutanoyl)oxy-3a,5,13-trihydroxy-2,5,8,8-tetramethyl-11-[(Z)-2-methylbut-2-enoyl]oxy-12-methylidene-4-oxo-1,2,3,9,10,11,13,13a-octahydrocyclopenta[12]annulen-9-yl] pyridine-3-carboxylate

Details

• Internal ID: 7d8501b1-656e-4db4-a5dc-12e2490ddeb4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Jatrophane and cyclojatrophane diterpenoids
• IUPAC Name: [(1S,2S,3aR,5R,6Z,9S,10S,11S,13R,13aS)-10-acetyloxy-1-(3-hydroperoxy-2-methylidenebutanoyl)oxy-3a,5,13-trihydroxy-2,5,8,8-tetramethyl-11-[(Z)-2-methylbut-2-enoyl]oxy-12-methylidene-4-oxo-1,2,3,9,10,11,13,13a-octahydrocyclopenta[12]annulen-9-yl] pyridine-3-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(C(C=CC(C(=O)C2(CC(C(C2C(C1=C)O)OC(=O)C(=C)C(C)OO)C)O)(C)O)(C)C)OC(=O)C3=CN=CC=C3)OC(=O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@H]([C@H](C(/C=C\[C@@](C(=O)[C@]2(C[C@@H]([C@@H]([C@@H]2[C@H](C1=C)O)OC(=O)C(=C)C(C)OO)C)O)(C)O)(C)C)OC(=O)C3=CN=CC=C3)OC(=O)C
• InChI: InChI=1S/C38H49NO14/c1-11-19(2)32(42)51-29-22(5)27(41)26-28(50-33(43)21(4)23(6)53-48)20(3)17-38(26,47)35(45)37(10,46)15-14-36(8,9)31(30(29)49-24(7)40)52-34(44)25-13-12-16-39-18-25/h11-16,18,20,23,26-31,41,46-48H,4-5,17H2,1-3,6-10H3/b15-14-,19-11-/t20-,23?,26-,27-,28-,29-,30+,31+,37+,38+/m0/s1
• InChI Key: UYWMRBXGOAEPNN-CTWYLCLXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₉NO₁₄
• Molecular Weight: 743.80 g/mol
• Exact Mass: 743.31530524 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 15
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8597	85.97%
Caco-2	-	0.8596	85.96%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4910	49.10%
OATP2B1 inhibitior	-	0.5740	57.40%
OATP1B1 inhibitior	+	0.8539	85.39%
OATP1B3 inhibitior	+	0.9303	93.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9612	96.12%
P-glycoprotein inhibitior	+	0.8065	80.65%
P-glycoprotein substrate	+	0.6889	68.89%
CYP3A4 substrate	+	0.7046	70.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8977	89.77%
CYP3A4 inhibition	-	0.7192	71.92%
CYP2C9 inhibition	-	0.7496	74.96%
CYP2C19 inhibition	-	0.7279	72.79%
CYP2D6 inhibition	-	0.8956	89.56%
CYP1A2 inhibition	-	0.7268	72.68%
CYP2C8 inhibition	+	0.7245	72.45%
CYP inhibitory promiscuity	-	0.7438	74.38%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.5093	50.93%
Eye corrosion	-	0.9807	98.07%
Eye irritation	-	0.9067	90.67%
Skin irritation	-	0.7202	72.02%
Skin corrosion	-	0.9119	91.19%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6413	64.13%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6699	66.99%
skin sensitisation	-	0.7653	76.53%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.4792	47.92%
Acute Oral Toxicity (c)	III	0.5102	51.02%
Estrogen receptor binding	+	0.7883	78.83%
Androgen receptor binding	+	0.6711	67.11%
Thyroid receptor binding	+	0.6582	65.82%
Glucocorticoid receptor binding	+	0.7640	76.40%
Aromatase binding	+	0.6313	63.13%
PPAR gamma	+	0.7470	74.70%
Honey bee toxicity	-	0.6692	66.92%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8828	88.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	98.14%	89.34%
CHEMBL2581	P07339	Cathepsin D	98.05%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.92%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.61%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.19%	91.49%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.82%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	93.38%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.93%	99.23%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	91.73%	92.88%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.73%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.16%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	90.83%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.55%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.89%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.89%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.73%	98.75%
CHEMBL2535	P11166	Glucose transporter	86.21%	98.75%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.93%	95.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.40%	93.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.77%	100.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.98%	91.38%
CHEMBL4208	P20618	Proteasome component C5	82.15%	90.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.07%	96.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.25%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.08%	100.00%

Plants that contains it

• Euphorbia amygdaloides

Cross-Links

• PubChem: 102511220
• LOTUS: LTS0046847
• wikiData: Q105281998