(5aR,9R,9aS,9bS)-9-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: d5d8ae6c-d55b-4299-b6a0-fa4bbfb51729
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (5aR,9R,9aS,9bS)-9-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC12CCCC(C1C3C(CC2)C(=C)C(=O)O3)(C)O
• SMILES (Isomeric): C[C@]12CCC[C@@]([C@@H]1[C@@H]3C(CC2)C(=C)C(=O)O3)(C)O
• InChI: InChI=1S/C15H22O3/c1-9-10-5-8-14(2)6-4-7-15(3,17)12(14)11(10)18-13(9)16/h10-12,17H,1,4-8H2,2-3H3/t10?,11-,12+,14+,15+/m0/s1
• InChI Key: BVRDNJZFYKHRJQ-IFBZQCCDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.7400	74.00%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6757	67.57%
OATP2B1 inhibitior	-	0.8509	85.09%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	+	0.8862	88.62%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5651	56.51%
BSEP inhibitior	-	0.9740	97.40%
P-glycoprotein inhibitior	-	0.8830	88.30%
P-glycoprotein substrate	-	0.9158	91.58%
CYP3A4 substrate	+	0.5731	57.31%
CYP2C9 substrate	-	0.7872	78.72%
CYP2D6 substrate	-	0.8625	86.25%
CYP3A4 inhibition	-	0.5439	54.39%
CYP2C9 inhibition	-	0.8958	89.58%
CYP2C19 inhibition	-	0.7093	70.93%
CYP2D6 inhibition	-	0.9578	95.78%
CYP1A2 inhibition	-	0.6420	64.20%
CYP2C8 inhibition	-	0.7591	75.91%
CYP inhibitory promiscuity	-	0.9199	91.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4804	48.04%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.8186	81.86%
Skin irritation	+	0.5999	59.99%
Skin corrosion	-	0.8988	89.88%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5913	59.13%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6824	68.24%
skin sensitisation	-	0.7082	70.82%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.6349	63.49%
Acute Oral Toxicity (c)	III	0.3104	31.04%
Estrogen receptor binding	+	0.7231	72.31%
Androgen receptor binding	+	0.5731	57.31%
Thyroid receptor binding	-	0.5362	53.62%
Glucocorticoid receptor binding	+	0.6054	60.54%
Aromatase binding	-	0.5996	59.96%
PPAR gamma	-	0.6469	64.69%
Honey bee toxicity	-	0.8706	87.06%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9939	99.39%

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	96.49%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.10%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.60%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.44%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.99%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	85.77%	97.79%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.96%	93.03%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.47%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.11%	100.00%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	81.70%	88.81%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.39%	92.94%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.31%	85.14%

Plants that contains it

• Artemisia arbuscula
• Aucklandia costus

Cross-Links

• PubChem: 11086187
• NPASS: NPC279748