Stypoldione

Details

• Internal ID: bf90063c-a6e9-4249-934b-c9af6aadb7cd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: (1S,2S,4aR,4bS,7S,8aR,10aR)-7-hydroxy-2,4b,7',8,8,10a-hexamethylspiro[2,3,4,4a,5,6,7,8a,9,10-decahydrophenanthrene-1,2'-3H-1-benzofuran]-4',5'-dione
• SMILES (Canonical): CC1CCC2C3(CCC(C(C3CCC2(C14CC5=C(O4)C(=CC(=O)C5=O)C)C)(C)C)O)C
• SMILES (Isomeric): C[C@H]1CC[C@@H]2[C@]3(CC[C@@H](C([C@@H]3CC[C@]2([C@]14CC5=C(O4)C(=CC(=O)C5=O)C)C)(C)C)O)C
• InChI: InChI=1S/C27H38O4/c1-15-13-18(28)22(30)17-14-27(31-23(15)17)16(2)7-8-20-25(5)11-10-21(29)24(3,4)19(25)9-12-26(20,27)6/h13,16,19-21,29H,7-12,14H2,1-6H3/t16-,19-,20+,21-,25-,26+,27-/m0/s1
• InChI Key: LLWMPGSQZXZZAE-JZFVXYNCSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₄
• Molecular Weight: 426.60 g/mol
• Exact Mass: 426.27700969 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 5.15
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 71103-05-4
• Y7JZ2J63Q7
• NSC339672
• NSC 339672
• (1S,2S,4aR,4bS,7S,8aR,10aR)-7-hydroxy-2,4b,7',8,8,10a-hexamethylspiro[2,3,4,4a,5,6,7,8a,9,10-decahydrophenanthrene-1,2'-3H-1-benzofuran]-4',5'-dione
• NSC-339672
• UNII-Y7JZ2J63Q7
• XS177357
• (1S,2S,4aR,4bS,7S,8aR,10aR)-7-hydroxy-2,4b,7',8,8,10a-hexamethyl-spiro[2,3,4,4a,5,6,7,8a,9,10-decahydrophenanthrene-1,2'-3H-benzofuran]-4',5'-dione
• 16,24-Cyclo-13,17-secochola-16,20(22)-diene-23,24-dione, 14,17-epoxy-3-hydroxy-4,4,8-trimethyl-, (3beta,5alpha,13alpha)-
• Spiro[benzofuran-2(3H),1'(2'H)-phenanthrene]-4,5-dione, 3',4',4'a,4'b,5',6',7',8',8'a,9',10',10'a-dodecahydro-7'-hydroxy-2',4'b,7,8',8',10'a-hexamethyl-, (1'S,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-
• Spiro[benzofuran-2(3H),1'(2'H)-phenanthrene]-4,5-dione, 3',4',4'a,4'b,5',6',7',8',8'a,9',10',10'a-dodecahydro-7'-hydroxy-2',4'b,7,8',8',10'a-hexamethyl-, (2S,2'S,4b'S,7'S,10a'R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.5583	55.83%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8137	81.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8913	89.13%
OATP1B3 inhibitior	+	0.9165	91.65%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.6583	65.83%
BSEP inhibitior	+	0.9398	93.98%
P-glycoprotein inhibitior	-	0.4432	44.32%
P-glycoprotein substrate	-	0.7806	78.06%
CYP3A4 substrate	+	0.6807	68.07%
CYP2C9 substrate	-	0.7752	77.52%
CYP2D6 substrate	-	0.8623	86.23%
CYP3A4 inhibition	-	0.6969	69.69%
CYP2C9 inhibition	-	0.8149	81.49%
CYP2C19 inhibition	-	0.7495	74.95%
CYP2D6 inhibition	-	0.9484	94.84%
CYP1A2 inhibition	-	0.7686	76.86%
CYP2C8 inhibition	-	0.7995	79.95%
CYP inhibitory promiscuity	-	0.9224	92.24%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5086	50.86%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9102	91.02%
Skin irritation	+	0.6334	63.34%
Skin corrosion	-	0.9053	90.53%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6761	67.61%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6592	65.92%
skin sensitisation	-	0.7907	79.07%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7762	77.62%
Acute Oral Toxicity (c)	III	0.3997	39.97%
Estrogen receptor binding	+	0.8684	86.84%
Androgen receptor binding	+	0.7607	76.07%
Thyroid receptor binding	+	0.6409	64.09%
Glucocorticoid receptor binding	+	0.8355	83.55%
Aromatase binding	+	0.7715	77.15%
PPAR gamma	+	0.7123	71.23%
Honey bee toxicity	-	0.7967	79.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9887	98.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1937	Q92769	Histone deacetylase 2	94.25%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.86%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.64%	98.95%
CHEMBL325	Q13547	Histone deacetylase 1	90.75%	95.92%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.04%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.43%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	88.84%	86.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.36%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.92%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.82%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.94%	96.61%
CHEMBL1871	P10275	Androgen Receptor	84.66%	96.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.49%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.03%	92.94%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.42%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.01%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.98%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.31%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.78%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.61%	82.69%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.17%	90.71%

Plants that contains it

• Catunaregam spinosa
• Polygala sibirica
• Solanum lycopersicum

Cross-Links

• PubChem: 3034636
• NPASS: NPC120096
• LOTUS: LTS0255611
• wikiData: Q104252448