4-[2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-2-oxoethyl]-2H-furan-5-one

Details

• Internal ID: 323ff63c-b985-4fbf-9aaa-55838ab9be23
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 4-[2-[6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-2-oxoethyl]-2H-furan-5-one
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2C(=O)CC3=CCOC3=O)(C)CO)O
• SMILES (Isomeric): CC12CCC(C(C1CCC(=C)C2C(=O)CC3=CCOC3=O)(C)CO)O
• InChI: InChI=1S/C20H28O5/c1-12-4-5-15-19(2,8-6-16(23)20(15,3)11-21)17(12)14(22)10-13-7-9-25-18(13)24/h7,15-17,21,23H,1,4-6,8-11H2,2-3H3
• InChI Key: WZHWNAKOQGIEEB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.17
• H-Bond Acceptor: 5
• 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	+	0.9418	94.18%
Caco-2	+	0.5854	58.54%
Blood Brain Barrier	+	0.6527	65.27%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7387	73.87%
OATP2B1 inhibitior	-	0.8658	86.58%
OATP1B1 inhibitior	+	0.8946	89.46%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	+	0.5640	56.40%
BSEP inhibitior	+	0.7690	76.90%
P-glycoprotein inhibitior	-	0.6765	67.65%
P-glycoprotein substrate	-	0.7701	77.01%
CYP3A4 substrate	+	0.6730	67.30%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.7092	70.92%
CYP2C9 inhibition	-	0.9115	91.15%
CYP2C19 inhibition	-	0.9282	92.82%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9092	90.92%
CYP2C8 inhibition	-	0.6970	69.70%
CYP inhibitory promiscuity	-	0.9078	90.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5856	58.56%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8861	88.61%
Skin irritation	+	0.5057	50.57%
Skin corrosion	-	0.9330	93.30%
Ames mutagenesis	-	0.6240	62.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.6569	65.69%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7327	73.27%
skin sensitisation	-	0.8998	89.98%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6711	67.11%
Acute Oral Toxicity (c)	III	0.5137	51.37%
Estrogen receptor binding	+	0.6023	60.23%
Androgen receptor binding	+	0.6873	68.73%
Thyroid receptor binding	+	0.6278	62.78%
Glucocorticoid receptor binding	+	0.7582	75.82%
Aromatase binding	+	0.5918	59.18%
PPAR gamma	-	0.5133	51.33%
Honey bee toxicity	-	0.8928	89.28%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9897	98.97%

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	94.90%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.70%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.56%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.61%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.87%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.80%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.44%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.06%	94.45%
CHEMBL5028	O14672	ADAM10	83.11%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.11%	86.33%
CHEMBL2581	P07339	Cathepsin D	82.02%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.58%	82.69%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 5316570
• LOTUS: LTS0021696
• wikiData: Q105323183