Spiro(azuleno(4,5-b)furan-3(2H),10'-(4H-6a,9)ethanoazuleno(4,5-b)furan)-2,2'(3'H)-dione, 4-(acetyloxy)-3a,3'a,4,5,5',6,6',6a,7,9',9a,9'a,9b,9'b-tetradecahydro-6,6'-dihydroxy-6,6',9,9'-tetramethyl-3'-methylene-, (3'aS-(3'aalpha,6'alpha,6'aa lpha,9'alpha,9'aalpha,9'bbeta,10'S*(3aS*,4R*,6S*,6aS*,9aS*,9bS*)))-

Details

• Internal ID: 34618507-a4b5-4553-a7d2-0cb5181146c5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: [(2'R,5R,6S,9'S,9bS)-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]-5-yl] acetate
• SMILES (Canonical): CC1=CCC2C1C3C(CC(C2(C)O)OC(=O)C)C4(CC56C=CC4(C5C7C(CCC6(C)O)C(=C)C(=O)O7)C)C(=O)O3
• SMILES (Isomeric): CC1=CCC2C1[C@@H]3C(C[C@H]([C@@]2(C)O)OC(=O)C)C4(CC56C=CC4(C5[C@@H]7C(CC[C@@]6(C)O)C(=C)C(=O)O7)C)C(=O)O3
• InChI: InChI=1S/C32H40O8/c1-15-7-8-19-22(15)24-20(13-21(30(19,6)37)38-17(3)33)32(27(35)40-24)14-31-12-11-28(32,4)25(31)23-18(9-10-29(31,5)36)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?/m1/s1
• InChI Key: DSNIKOZTDZBWKD-XMNJDQQWSA-N
• Popularity: 12 references 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

• ye ju-Hua
• Spiro(azuleno(4,5-b)furan-3(2H),10'-(4H-6a,9)ethanoazuleno(4,5-b)furan)-2,2'(3'H)-dione, 4-(acetyloxy)-3a,3'a,4,5,5',6,6',6a,7,9',9a,9'a,9b,9'b-tetradecahydro-6,6'-dihydroxy-6,6',9,9'-tetramethyl-3'-methylene-, (3'aS-(3'aalpha,6'alpha,6'aa lpha,9'alpha,9'aalpha,9'bbeta,10'S*(3aS*,4R*,6S*,6aS*,9aS*,9bS*)))-
• Handelin; Yejuhualactone
• DTXSID40978294
• 6,6'-Dihydroxy-6,6',9,9'-tetramethyl-3'-methylidene-2,2'-dioxo-2',3',3a,3'a,4,5,5',6,6',6a,7,9',9a,9'a,9b,9'b-hexadecahydro-2H,4'H-spiro[azuleno[4,5-b]furan-3,10'-[6a,9]ethanoazuleno[4,5-b]furan]-5-yl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9842	98.42%
Caco-2	-	0.7565	75.65%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7308	73.08%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.8499	84.99%
OATP1B3 inhibitior	+	0.8688	86.88%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8021	80.21%
BSEP inhibitior	+	0.7990	79.90%
P-glycoprotein inhibitior	+	0.6967	69.67%
P-glycoprotein substrate	+	0.5740	57.40%
CYP3A4 substrate	+	0.7265	72.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.5750	57.50%
CYP2C9 inhibition	-	0.7850	78.50%
CYP2C19 inhibition	-	0.8579	85.79%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.7083	70.83%
CYP2C8 inhibition	+	0.7367	73.67%
CYP inhibitory promiscuity	-	0.9574	95.74%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5524	55.24%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9201	92.01%
Skin irritation	+	0.5242	52.42%
Skin corrosion	-	0.9043	90.43%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7931	79.31%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.8023	80.23%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5394	53.94%
Acute Oral Toxicity (c)	III	0.3960	39.60%
Estrogen receptor binding	+	0.8106	81.06%
Androgen receptor binding	+	0.7822	78.22%
Thyroid receptor binding	+	0.5614	56.14%
Glucocorticoid receptor binding	+	0.7602	76.02%
Aromatase binding	+	0.7464	74.64%
PPAR gamma	+	0.7021	70.21%
Honey bee toxicity	-	0.6880	68.80%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9920	99.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.43%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.31%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.79%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.54%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.29%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.23%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	88.80%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.95%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.08%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.08%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.14%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.01%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.46%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.25%	95.89%
CHEMBL259	P32245	Melanocortin receptor 4	82.28%	95.38%
CHEMBL4040	P28482	MAP kinase ERK2	81.67%	83.82%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.60%	97.28%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.89%	93.04%

Plants that contains it

• Chrysanthemum indicum
• Lepidolopsis tadshikorum

Cross-Links

• PubChem: 3085251
• NPASS: NPC93984
• LOTUS: LTS0048089
• wikiData: Q72481053