[(1'R,2'R,3S,3aR,4S,5'S,6R,6aR,9'S,9aR,9bR,10'S,11'R)-2',6-dihydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7'-dioxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3,15'-8-oxatetracyclo[9.2.2.01,10.05,9]pentadec-12-ene]-4-yl] acetate

Details

• Internal ID: ab29fea1-acc4-4196-a090-7b67502470e6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: [(1'R,2'R,3S,3aR,4S,5'S,6R,6aR,9'S,9aR,9bR,10'S,11'R)-2',6-dihydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7'-dioxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-3,15'-8-oxatetracyclo[9.2.2.01,10.05,9]pentadec-12-ene]-4-yl] acetate
• SMILES (Canonical): CC1=CCC2C1C3C(C(CC2(C)O)OC(=O)C)C4(CC56C=CC4(C5C7C(CCC6(C)O)C(=C)C(=O)O7)C)C(=O)O3
• SMILES (Isomeric): CC1=CC[C@@H]2[C@H]1[C@@H]3[C@@H]([C@H](C[C@@]2(C)O)OC(=O)C)[C@]4(C[C@@]56C=C[C@@]4([C@@H]5[C@@H]7[C@@H](CC[C@@]6(C)O)C(=C)C(=O)O7)C)C(=O)O3
• InChI: InChI=1S/C32H40O8/c1-15-7-8-19-21(15)24-22(20(38-17(3)33)13-29(19,5)36)32(27(35)40-24)14-31-12-11-28(32,4)25(31)23-18(9-10-30(31,6)37)16(2)26(34)39-23/h7,11-12,18-25,36-37H,2,8-10,13-14H2,1,3-6H3/t18-,19+,20-,21-,22+,23-,24+,25-,28+,29+,30+,31-,32+/m0/s1
• InChI Key: SZQWAXGDCUONOB-QFASSNHESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₀O₈
• Molecular Weight: 552.70 g/mol
• Exact Mass: 552.27231823 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9870	98.70%
Caco-2	-	0.7551	75.51%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7105	71.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8546	85.46%
OATP1B3 inhibitior	+	0.8289	82.89%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8021	80.21%
BSEP inhibitior	+	0.8420	84.20%
P-glycoprotein inhibitior	+	0.7045	70.45%
P-glycoprotein substrate	+	0.6500	65.00%
CYP3A4 substrate	+	0.7327	73.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.5547	55.47%
CYP2C9 inhibition	-	0.7717	77.17%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9599	95.99%
CYP1A2 inhibition	-	0.6526	65.26%
CYP2C8 inhibition	+	0.7240	72.40%
CYP inhibitory promiscuity	-	0.9610	96.10%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5363	53.63%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9103	91.03%
Skin irritation	+	0.5232	52.32%
Skin corrosion	-	0.8919	89.19%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8248	82.48%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.7211	72.11%
skin sensitisation	-	0.7983	79.83%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6278	62.78%
Acute Oral Toxicity (c)	II	0.3847	38.47%
Estrogen receptor binding	+	0.8194	81.94%
Androgen receptor binding	+	0.7822	78.22%
Thyroid receptor binding	+	0.5887	58.87%
Glucocorticoid receptor binding	+	0.7681	76.81%
Aromatase binding	+	0.7177	71.77%
PPAR gamma	+	0.6885	68.85%
Honey bee toxicity	-	0.6616	66.16%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	501.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.78%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.41%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.54%	99.23%
CHEMBL2581	P07339	Cathepsin D	91.61%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.56%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.53%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.43%	97.25%
CHEMBL259	P32245	Melanocortin receptor 4	89.78%	95.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.76%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	88.32%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.26%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.49%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.99%	85.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.99%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.78%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.89%	97.28%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.80%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.64%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.81%	91.07%
CHEMBL1871	P10275	Androgen Receptor	82.64%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.80%	93.04%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.05%	96.09%
CHEMBL5028	O14672	ADAM10	80.55%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.44%	95.89%

Plants that contains it

• Chrysanthemum ornatum

Cross-Links

• PubChem: 162881546
• LOTUS: LTS0261075
• wikiData: Q105264337