(4E,4aS,7E,11aR)-4-[5-hydroxy-4-(hydroxymethyl)pent-3-enylidene]-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydrocyclonona[c]pyran-1-one

Details

• Internal ID: fefdf826-27c8-449f-9246-4d9cf6a7fb41
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4E,4aS,7E,11aR)-4-[5-hydroxy-4-(hydroxymethyl)pent-3-enylidene]-7-methyl-11-methylidene-4a,5,6,9,10,11a-hexahydrocyclonona[c]pyran-1-one
• SMILES (Canonical): CC1=CCCC(=C)C2C(CC1)C(=CCC=C(CO)CO)COC2=O
• SMILES (Isomeric): C/C/1=C\CCC(=C)[C@H]2[C@H](CC1)/C(=C\CC=C(CO)CO)/COC2=O
• InChI: InChI=1S/C20H28O4/c1-14-5-3-6-15(2)19-18(10-9-14)17(13-24-20(19)23)8-4-7-16(11-21)12-22/h5,7-8,18-19,21-22H,2-4,6,9-13H2,1H3/b14-5+,17-8-/t18-,19+/m1/s1
• InChI Key: JOKXSQBLJTXDIX-XIDCNVQJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 3.08
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8438	84.38%
Caco-2	-	0.5849	58.49%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5219	52.19%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.9160	91.60%
OATP1B3 inhibitior	+	0.9287	92.87%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6419	64.19%
BSEP inhibitior	+	0.8417	84.17%
P-glycoprotein inhibitior	-	0.6603	66.03%
P-glycoprotein substrate	-	0.7506	75.06%
CYP3A4 substrate	+	0.5887	58.87%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.7441	74.41%
CYP2C9 inhibition	-	0.8466	84.66%
CYP2C19 inhibition	-	0.7455	74.55%
CYP2D6 inhibition	-	0.8613	86.13%
CYP1A2 inhibition	-	0.6174	61.74%
CYP2C8 inhibition	-	0.6470	64.70%
CYP inhibitory promiscuity	-	0.9065	90.65%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7191	71.91%
Eye corrosion	-	0.9621	96.21%
Eye irritation	-	0.7395	73.95%
Skin irritation	-	0.7288	72.88%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	-	0.6644	66.44%
Human Ether-a-go-go-Related Gene inhibition	-	0.3902	39.02%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7960	79.60%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5254	52.54%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5351	53.51%
Acute Oral Toxicity (c)	III	0.5955	59.55%
Estrogen receptor binding	+	0.6243	62.43%
Androgen receptor binding	+	0.5580	55.80%
Thyroid receptor binding	+	0.5419	54.19%
Glucocorticoid receptor binding	+	0.6747	67.47%
Aromatase binding	+	0.5490	54.90%
PPAR gamma	+	0.6347	63.47%
Honey bee toxicity	-	0.9014	90.14%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9775	97.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.82%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.10%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.18%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.90%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.51%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.77%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.22%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	82.78%	94.73%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.13%	86.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.46%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 21627148
• LOTUS: LTS0090772
• wikiData: Q105132399