[(1R,2R,5R,6S,7S,8S,11S,12R)-2,6,8,11,12-pentahydroxy-11-(hydroxymethyl)-3,7-dimethyl-14-oxo-4-propan-2-yl-13-oxatetracyclo[5.5.3.01,8.02,6]pentadec-3-en-5-yl] 1H-pyrrole-2-carboxylate

Details

• Internal ID: a736733c-25a5-4f5b-a411-3a108d7e47da
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1R,2R,5R,6S,7S,8S,11S,12R)-2,6,8,11,12-pentahydroxy-11-(hydroxymethyl)-3,7-dimethyl-14-oxo-4-propan-2-yl-13-oxatetracyclo[5.5.3.01,8.02,6]pentadec-3-en-5-yl] 1H-pyrrole-2-carboxylate
• SMILES (Canonical): CC1=C(C(C2(C1(C34C(C(CCC3(C2(CC(=O)O4)C)O)(CO)O)O)O)O)OC(=O)C5=CC=CN5)C(C)C
• SMILES (Isomeric): CC1=C([C@H]([C@@]2([C@]1([C@@]34[C@@H]([C@](CC[C@@]3([C@@]2(CC(=O)O4)C)O)(CO)O)O)O)O)OC(=O)C5=CC=CN5)C(C)C
• InChI: InChI=1S/C25H33NO10/c1-12(2)16-13(3)23(33)24(34,17(16)35-18(29)14-6-5-9-26-14)20(4)10-15(28)36-25(23)19(30)21(31,11-27)7-8-22(20,25)32/h5-6,9,12,17,19,26-27,30-34H,7-8,10-11H2,1-4H3/t17-,19-,20+,21+,22+,23-,24-,25-/m1/s1
• InChI Key: JBYNLPJMCTVJAE-HEYMRSJXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₃NO₁₀
• Molecular Weight: 507.50 g/mol
• Exact Mass: 507.21044625 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -0.70
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8643	86.43%
Caco-2	-	0.8116	81.16%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5278	52.78%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.8502	85.02%
OATP1B3 inhibitior	+	0.9211	92.11%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5447	54.47%
P-glycoprotein inhibitior	-	0.4581	45.81%
P-glycoprotein substrate	+	0.5531	55.31%
CYP3A4 substrate	+	0.7094	70.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8665	86.65%
CYP3A4 inhibition	-	0.7065	70.65%
CYP2C9 inhibition	-	0.8091	80.91%
CYP2C19 inhibition	-	0.8676	86.76%
CYP2D6 inhibition	-	0.9244	92.44%
CYP1A2 inhibition	-	0.7646	76.46%
CYP2C8 inhibition	+	0.4521	45.21%
CYP inhibitory promiscuity	-	0.7508	75.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5570	55.70%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9124	91.24%
Skin irritation	-	0.6786	67.86%
Skin corrosion	-	0.9301	93.01%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4694	46.94%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5478	54.78%
skin sensitisation	-	0.8516	85.16%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8094	80.94%
Acute Oral Toxicity (c)	III	0.7120	71.20%
Estrogen receptor binding	+	0.7086	70.86%
Androgen receptor binding	+	0.7471	74.71%
Thyroid receptor binding	-	0.5126	51.26%
Glucocorticoid receptor binding	+	0.6632	66.32%
Aromatase binding	+	0.7033	70.33%
PPAR gamma	-	0.5085	50.85%
Honey bee toxicity	-	0.7853	78.53%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6550	65.50%
Fish aquatic toxicity	+	0.9510	95.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.44%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.02%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.60%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	95.93%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	95.13%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.42%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.95%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.88%	97.25%
CHEMBL299	P17252	Protein kinase C alpha	92.14%	98.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.93%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.07%	95.89%
CHEMBL4208	P20618	Proteasome component C5	88.63%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.80%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.06%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.43%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.28%	82.69%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.97%	89.67%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.51%	95.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.42%	93.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.83%	97.28%

Plants that contains it

• Ryania speciosa

Cross-Links

• PubChem: 163195219
• LOTUS: LTS0032064
• wikiData: Q105124654