(4R,4aS,10aR,11aR,11bS)-4-(hydroxymethyl)-4,8,11b-trimethyl-2,3,4a,5,6,10a,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-9-one

Details

• Internal ID: 6b69596c-5598-4a5b-80c2-66f7806aacb2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (4R,4aS,10aR,11aR,11bS)-4-(hydroxymethyl)-4,8,11b-trimethyl-2,3,4a,5,6,10a,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-9-one
• InChI: InChI=1S/C20H28O3/c1-12-14-9-13-5-6-17-19(2,11-21)7-4-8-20(17,3)15(13)10-16(14)23-18(12)22/h9,15-17,21H,4-8,10-11H2,1-3H3/t15-,16-,17-,19+,20+/m1/s1
• InChI Key: NZAUOMAFRGQWRI-QKMNUUQDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.77
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.8627	86.27%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7891	78.91%
OATP2B1 inhibitior	-	0.8666	86.66%
OATP1B1 inhibitior	+	0.8017	80.17%
OATP1B3 inhibitior	+	0.9513	95.13%
MATE1 inhibitior	-	0.7812	78.12%
OCT2 inhibitior	+	0.6898	68.98%
BSEP inhibitior	+	0.6499	64.99%
P-glycoprotein inhibitior	-	0.7264	72.64%
P-glycoprotein substrate	-	0.8067	80.67%
CYP3A4 substrate	+	0.6435	64.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8876	88.76%
CYP3A4 inhibition	+	0.5221	52.21%
CYP2C9 inhibition	-	0.8218	82.18%
CYP2C19 inhibition	-	0.7880	78.80%
CYP2D6 inhibition	-	0.9315	93.15%
CYP1A2 inhibition	-	0.7652	76.52%
CYP2C8 inhibition	-	0.7333	73.33%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5473	54.73%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9495	94.95%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9472	94.72%
Ames mutagenesis	-	0.7670	76.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8025	80.25%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6318	63.18%
skin sensitisation	-	0.8549	85.49%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7765	77.65%
Acute Oral Toxicity (c)	III	0.6767	67.67%
Estrogen receptor binding	+	0.6715	67.15%
Androgen receptor binding	+	0.6402	64.02%
Thyroid receptor binding	+	0.6803	68.03%
Glucocorticoid receptor binding	+	0.8282	82.82%
Aromatase binding	+	0.5980	59.80%
PPAR gamma	+	0.6331	63.31%
Honey bee toxicity	-	0.9151	91.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9866	98.66%

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	95.40%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.93%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.44%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.98%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.74%	86.33%
CHEMBL2581	P07339	Cathepsin D	87.60%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.17%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.00%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.22%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.15%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.19%	94.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.14%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.63%	85.14%

Plants that contains it

• Phlogacanthus curviflorus

Cross-Links

• PubChem: 56945586
• LOTUS: LTS0035278
• wikiData: Q105187810