[(2R,3R,3aR,4S,7S,7aR)-3-acetyloxy-7,7a-dimethyl-4'-methylidene-2'-oxospiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane]-4-yl] 3-hydroxy-2-methylidenebutanoate

Details

• Internal ID: 6297c2d5-77e7-4de1-b148-1036a3a5b3fe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(2R,3R,3aR,4S,7S,7aR)-3-acetyloxy-7,7a-dimethyl-4'-methylidene-2'-oxospiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane]-4-yl] 3-hydroxy-2-methylidenebutanoate
• SMILES (Canonical): CC1CCC(C2C1(CC3(C2OC(=O)C)C(=C)COC3=O)C)OC(=O)C(=C)C(C)O
• SMILES (Isomeric): C[C@H]1CC[C@@H]([C@H]2[C@@]1(C[C@]3([C@@H]2OC(=O)C)C(=C)COC3=O)C)OC(=O)C(=C)C(C)O
• InChI: InChI=1S/C22H30O7/c1-11-7-8-16(29-19(25)13(3)14(4)23)17-18(28-15(5)24)22(10-21(11,17)6)12(2)9-27-20(22)26/h11,14,16-18,23H,2-3,7-10H2,1,4-6H3/t11-,14?,16-,17+,18+,21+,22+/m0/s1
• InChI Key: JYHIRKVWRPNDHA-PMHKWGJISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₇
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.19915329 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	-	0.5506	55.06%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7596	75.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8966	89.66%
OATP1B3 inhibitior	+	0.8964	89.64%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5521	55.21%
BSEP inhibitior	-	0.8846	88.46%
P-glycoprotein inhibitior	-	0.5108	51.08%
P-glycoprotein substrate	-	0.6492	64.92%
CYP3A4 substrate	+	0.6560	65.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8795	87.95%
CYP3A4 inhibition	-	0.7097	70.97%
CYP2C9 inhibition	-	0.8476	84.76%
CYP2C19 inhibition	-	0.9031	90.31%
CYP2D6 inhibition	-	0.9593	95.93%
CYP1A2 inhibition	+	0.5210	52.10%
CYP2C8 inhibition	-	0.6374	63.74%
CYP inhibitory promiscuity	-	0.9495	94.95%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5964	59.64%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.9102	91.02%
Skin irritation	+	0.5480	54.80%
Skin corrosion	-	0.9207	92.07%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6353	63.53%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.7181	71.81%
skin sensitisation	-	0.8327	83.27%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.8239	82.39%
Acute Oral Toxicity (c)	III	0.4986	49.86%
Estrogen receptor binding	+	0.7941	79.41%
Androgen receptor binding	+	0.6090	60.90%
Thyroid receptor binding	+	0.5527	55.27%
Glucocorticoid receptor binding	+	0.7534	75.34%
Aromatase binding	+	0.6608	66.08%
PPAR gamma	+	0.6749	67.49%
Honey bee toxicity	-	0.6200	62.00%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5750	57.50%
Fish aquatic toxicity	+	0.9942	99.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.65%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.49%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.55%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.51%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.49%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	91.87%	91.19%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.16%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.84%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.32%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.72%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.50%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.81%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.74%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.07%	95.89%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	83.74%	92.78%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.19%	89.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.78%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.76%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.24%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.03%	96.38%

Plants that contains it

• Petasites formosanus

Cross-Links

• PubChem: 10811313
• LOTUS: LTS0184340
• wikiData: Q105137013