2-[(1S,4S,5R,6R,9S,10R,12R,14R)-7-[(4S)-5-[[(1R,2R,3aR,5S,6E,10R,11S,13R,13aS)-1,2,3a,11,13-pentaacetyloxy-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-3,5,10,11,13,13a-hexahydro-1H-cyclopenta[12]annulen-10-yl]oxy]-4-methyl-2-oxopentyl]-6-(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl]acetic acid

Details

• Internal ID: ca865c5b-6ef3-4f97-b7b8-a687557e2c7f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Jatrophane and cyclojatrophane diterpenoids
• IUPAC Name: 2-[(1S,4S,5R,6R,9S,10R,12R,14R)-7-[(4S)-5-[[(1R,2R,3aR,5S,6E,10R,11S,13R,13aS)-1,2,3a,11,13-pentaacetyloxy-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-3,5,10,11,13,13a-hexahydro-1H-cyclopenta[12]annulen-10-yl]oxy]-4-methyl-2-oxopentyl]-6-(carboxymethyl)-5-hydroxy-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl]acetic acid
• InChI: InChI=1S/C59H78O20/c1-27(18-38(65)20-37-21-39-45-42(55(45,13)14)19-30(4)57(51(39)71)24-29(3)40(22-43(66)67)59(57,73)41(37)23-44(68)69)25-74-49-48(76-33(7)61)31(5)47(75-32(6)60)46-53(77-34(8)62)56(15,78-35(9)63)26-58(46,79-36(10)64)50(70)28(2)16-17-54(11,12)52(49)72/h16-17,21,24,27-28,30,39-42,45-49,53,73H,5,18-20,22-23,25-26H2,1-4,6-15H3,(H,66,67)(H,68,69)/b17-16+/t27-,28-,30+,39-,40-,41+,42+,45-,46-,47-,48-,49+,53+,56+,57-,58+,59+/m0/s1
• InChI Key: CMLRTBRDPZXMDV-UQPPTKJNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₇₈O₂₀
• Molecular Weight: 1107.20 g/mol
• Exact Mass: 1106.50864487 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 6.02
• H-Bond Acceptor: 18
• H-Bond Donor: 3
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9825	98.25%
Caco-2	-	0.8573	85.73%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7508	75.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8166	81.66%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9457	94.57%
BSEP inhibitior	+	0.9448	94.48%
P-glycoprotein inhibitior	+	0.7520	75.20%
P-glycoprotein substrate	+	0.8341	83.41%
CYP3A4 substrate	+	0.7397	73.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.6610	66.10%
CYP2C9 inhibition	-	0.5255	52.55%
CYP2C19 inhibition	-	0.8112	81.12%
CYP2D6 inhibition	-	0.9443	94.43%
CYP1A2 inhibition	-	0.7966	79.66%
CYP2C8 inhibition	+	0.7904	79.04%
CYP inhibitory promiscuity	-	0.9335	93.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6631	66.31%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.8983	89.83%
Skin irritation	-	0.5791	57.91%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	+	0.5536	55.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6723	67.23%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5845	58.45%
skin sensitisation	-	0.7838	78.38%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5432	54.32%
Acute Oral Toxicity (c)	III	0.3711	37.11%
Estrogen receptor binding	+	0.7164	71.64%
Androgen receptor binding	+	0.7759	77.59%
Thyroid receptor binding	+	0.6526	65.26%
Glucocorticoid receptor binding	+	0.7707	77.07%
Aromatase binding	+	0.6777	67.77%
PPAR gamma	+	0.8087	80.87%
Honey bee toxicity	-	0.6275	62.75%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9962	99.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.10%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.52%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.72%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.37%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	93.67%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.15%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.10%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.71%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	90.82%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.56%	94.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.68%	93.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.24%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.51%	95.56%
CHEMBL5028	O14672	ADAM10	87.25%	97.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.04%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.62%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	84.55%	89.63%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.06%	97.21%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.55%	89.34%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.08%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.72%	89.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.67%	89.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.53%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.67%	96.90%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.15%	95.71%

Plants that contains it

• Euphorbia paralias

Cross-Links

• PubChem: 162817223
• LOTUS: LTS0178540
• wikiData: Q104964840