4-[2-[(1R,4aS,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one

Details

• Internal ID: 75678cf6-8d48-4d18-9fb7-2354c0a95878
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 4-[2-[(1R,4aS,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one
• SMILES (Canonical): CC12CCC(=O)C(C1CCC(=C)C2CCC3=CCOC3=O)(C)CO
• SMILES (Isomeric): C[C@@]12CCC(=O)[C@@]([C@H]1CCC(=C)[C@H]2CCC3=CCOC3=O)(C)CO
• InChI: InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h9,15-16,21H,1,4-8,10-12H2,2-3H3/t15-,16+,19+,20+/m1/s1
• InChI Key: ROPZFDGMJDAXOR-LPWQTFTOSA-N
• Popularity: 2 references 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): 63.60 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 4
• 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	+	0.9632	96.32%
Caco-2	+	0.6742	67.42%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7441	74.41%
OATP2B1 inhibitior	-	0.8661	86.61%
OATP1B1 inhibitior	+	0.8880	88.80%
OATP1B3 inhibitior	+	0.9383	93.83%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	+	0.6412	64.12%
BSEP inhibitior	+	0.6291	62.91%
P-glycoprotein inhibitior	-	0.6139	61.39%
P-glycoprotein substrate	-	0.7608	76.08%
CYP3A4 substrate	+	0.6389	63.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9084	90.84%
CYP3A4 inhibition	-	0.6477	64.77%
CYP2C9 inhibition	-	0.9135	91.35%
CYP2C19 inhibition	-	0.8917	89.17%
CYP2D6 inhibition	-	0.9434	94.34%
CYP1A2 inhibition	-	0.7769	77.69%
CYP2C8 inhibition	-	0.6641	66.41%
CYP inhibitory promiscuity	-	0.8903	89.03%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5423	54.23%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.8190	81.90%
Skin irritation	+	0.5403	54.03%
Skin corrosion	-	0.9187	91.87%
Ames mutagenesis	-	0.6724	67.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.3646	36.46%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6976	69.76%
skin sensitisation	-	0.8787	87.87%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5406	54.06%
Acute Oral Toxicity (c)	III	0.6412	64.12%
Estrogen receptor binding	+	0.6452	64.52%
Androgen receptor binding	+	0.6783	67.83%
Thyroid receptor binding	+	0.7205	72.05%
Glucocorticoid receptor binding	+	0.7926	79.26%
Aromatase binding	+	0.6363	63.63%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8843	88.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9935	99.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.66%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.13%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.13%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.37%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.05%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.38%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.25%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.25%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.68%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.73%	92.62%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 44577190
• NPASS: NPC51486
• ChEMBL: CHEMBL511890
• LOTUS: LTS0135055
• wikiData: Q105242398