4-[2-[(1R,4aR,6R,8aS)-6-hydroxy-5,5-bis(hydroxymethyl)-8a-methyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one

Details

• Internal ID: 422c694c-88d0-4738-bf0d-e9cbcfab31c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 4-[2-[(1R,4aR,6R,8aS)-6-hydroxy-5,5-bis(hydroxymethyl)-8a-methyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2CCC3=CCOC3=O)(CO)CO)O
• SMILES (Isomeric): C[C@@]12CC[C@H](C([C@@H]1CCC(=C)[C@H]2CCC3=CCOC3=O)(CO)CO)O
• InChI: InChI=1S/C20H30O5/c1-13-3-6-16-19(2,9-7-17(23)20(16,11-21)12-22)15(13)5-4-14-8-10-25-18(14)24/h8,15-17,21-23H,1,3-7,9-12H2,2H3/t15-,16-,17-,19+/m1/s1
• InChI Key: RQPNDCVTRUVOKO-MTNOOBJLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.20932405 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.96
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9550	95.50%
Caco-2	+	0.5465	54.65%
Blood Brain Barrier	+	0.5277	52.77%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6457	64.57%
OATP2B1 inhibitior	-	0.8626	86.26%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	+	0.5261	52.61%
BSEP inhibitior	+	0.6948	69.48%
P-glycoprotein inhibitior	-	0.7764	77.64%
P-glycoprotein substrate	-	0.7528	75.28%
CYP3A4 substrate	+	0.6717	67.17%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8794	87.94%
CYP3A4 inhibition	-	0.8484	84.84%
CYP2C9 inhibition	-	0.9061	90.61%
CYP2C19 inhibition	-	0.8678	86.78%
CYP2D6 inhibition	-	0.9314	93.14%
CYP1A2 inhibition	-	0.8759	87.59%
CYP2C8 inhibition	-	0.7105	71.05%
CYP inhibitory promiscuity	-	0.8741	87.41%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5671	56.71%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8118	81.18%
Skin irritation	-	0.5346	53.46%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4010	40.10%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6726	67.26%
skin sensitisation	-	0.8844	88.44%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4867	48.67%
Acute Oral Toxicity (c)	III	0.5333	53.33%
Estrogen receptor binding	+	0.6797	67.97%
Androgen receptor binding	+	0.7262	72.62%
Thyroid receptor binding	+	0.6525	65.25%
Glucocorticoid receptor binding	+	0.8321	83.21%
Aromatase binding	+	0.6391	63.91%
PPAR gamma	-	0.5488	54.88%
Honey bee toxicity	-	0.8500	85.00%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9827	98.27%

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	97.13%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.08%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.01%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.26%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.31%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.84%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.27%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.54%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.44%	82.69%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 162880770
• LOTUS: LTS0253316
• wikiData: Q105243503