[(1R,2R,5R,6S,7S,8S,10S,12R)-2,6,8,10,12-pentahydroxy-3,7-dimethyl-11-methylidene-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: d7544550-8a1e-4be7-9847-26413976efbf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1R,2R,5R,6S,7S,8S,10S,12R)-2,6,8,10,12-pentahydroxy-3,7-dimethyl-11-methylidene-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(=C)C(CC3(C2(CC(=O)O4)C)O)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(=C)[C@H](C[C@@]3([C@@]2(CC(=O)O4)C)O)O)O)O)O)OC(=O)C5=CC=CN5)C(C)C
• InChI: InChI=1S/C25H31NO9/c1-11(2)17-13(4)23(32)24(33,19(17)34-20(30)14-7-6-8-26-14)21(5)10-16(28)35-25(23)18(29)12(3)15(27)9-22(21,25)31/h6-8,11,15,18-19,26-27,29,31-33H,3,9-10H2,1-2,4-5H3/t15-,18+,19+,21-,22-,23+,24+,25+/m0/s1
• InChI Key: INKREVWPFYFIDX-PNKLSOHESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₁NO₉
• Molecular Weight: 489.50 g/mol
• Exact Mass: 489.19988157 g/mol
• Topological Polar Surface Area (TPSA): 170.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): 0.11
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9259	92.59%
Caco-2	-	0.8265	82.65%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.3301	33.01%
OATP2B1 inhibitior	-	0.8512	85.12%
OATP1B1 inhibitior	+	0.8672	86.72%
OATP1B3 inhibitior	+	0.9281	92.81%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8067	80.67%
P-glycoprotein inhibitior	-	0.4891	48.91%
P-glycoprotein substrate	+	0.5293	52.93%
CYP3A4 substrate	+	0.7148	71.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8646	86.46%
CYP3A4 inhibition	-	0.7904	79.04%
CYP2C9 inhibition	-	0.8200	82.00%
CYP2C19 inhibition	-	0.7897	78.97%
CYP2D6 inhibition	-	0.8803	88.03%
CYP1A2 inhibition	-	0.7636	76.36%
CYP2C8 inhibition	+	0.5182	51.82%
CYP inhibitory promiscuity	-	0.7652	76.52%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5136	51.36%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8947	89.47%
Skin irritation	-	0.7209	72.09%
Skin corrosion	-	0.9179	91.79%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3871	38.71%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8044	80.44%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7265	72.65%
Acute Oral Toxicity (c)	III	0.6260	62.60%
Estrogen receptor binding	+	0.5817	58.17%
Androgen receptor binding	+	0.7301	73.01%
Thyroid receptor binding	-	0.5058	50.58%
Glucocorticoid receptor binding	+	0.6481	64.81%
Aromatase binding	+	0.6345	63.45%
PPAR gamma	+	0.5436	54.36%
Honey bee toxicity	-	0.7353	73.53%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.9799	97.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.34%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.51%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.78%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.51%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	91.89%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.38%	91.11%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.28%	91.07%
CHEMBL2996	Q05655	Protein kinase C delta	90.41%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.16%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.77%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.60%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	86.44%	94.75%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.05%	93.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.37%	89.67%
CHEMBL4208	P20618	Proteasome component C5	84.60%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.47%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.41%	93.99%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.23%	90.08%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.49%	96.47%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.41%	97.25%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.29%	95.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.55%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	81.30%	98.03%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.45%	97.28%

Plants that contains it

• Ryania speciosa

Cross-Links

• PubChem: 101177509
• LOTUS: LTS0266255
• wikiData: Q105116271