(4aR,5S,8R,8aR,9aR)-8a,9a-dihydroxy-8-methoxy-3,4a,5-trimethyl-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: c52b896c-c3db-4b01-b5d8-5cf6e5bd4083
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aR,5S,8R,8aR,9aR)-8a,9a-dihydroxy-8-methoxy-3,4a,5-trimethyl-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCC(C2(C1(CC3=C(C(=O)OC3(C2)O)C)C)O)OC
• SMILES (Isomeric): C[C@H]1CC[C@H]([C@@]2([C@@]1(CC3=C(C(=O)O[C@@]3(C2)O)C)C)O)OC
• InChI: InChI=1S/C16H24O5/c1-9-5-6-12(20-4)15(18)8-16(19)11(7-14(9,15)3)10(2)13(17)21-16/h9,12,18-19H,5-8H2,1-4H3/t9-,12+,14+,15-,16+/m0/s1
• InChI Key: IWUVIUALYNGRST-BRHOPSAPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₅
• Molecular Weight: 296.36 g/mol
• Exact Mass: 296.16237386 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9821	98.21%
Caco-2	+	0.6593	65.93%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6927	69.27%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.9104	91.04%
OATP1B3 inhibitior	+	0.9136	91.36%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.8701	87.01%
P-glycoprotein inhibitior	-	0.8909	89.09%
P-glycoprotein substrate	-	0.8326	83.26%
CYP3A4 substrate	+	0.6446	64.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8816	88.16%
CYP3A4 inhibition	-	0.6809	68.09%
CYP2C9 inhibition	-	0.7993	79.93%
CYP2C19 inhibition	-	0.8047	80.47%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.6517	65.17%
CYP2C8 inhibition	-	0.8395	83.95%
CYP inhibitory promiscuity	-	0.8631	86.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4958	49.58%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.7485	74.85%
Skin irritation	+	0.5657	56.57%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4247	42.47%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5717	57.17%
skin sensitisation	-	0.8678	86.78%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6649	66.49%
Acute Oral Toxicity (c)	I	0.3798	37.98%
Estrogen receptor binding	+	0.5308	53.08%
Androgen receptor binding	+	0.5858	58.58%
Thyroid receptor binding	+	0.7371	73.71%
Glucocorticoid receptor binding	+	0.6320	63.20%
Aromatase binding	+	0.5490	54.90%
PPAR gamma	-	0.5771	57.71%
Honey bee toxicity	-	0.8465	84.65%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9747	97.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.19%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.83%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.07%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.83%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.32%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.01%	99.23%
CHEMBL1871	P10275	Androgen Receptor	85.59%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.17%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.79%	85.14%
CHEMBL1902	P62942	FK506-binding protein 1A	83.16%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.49%	95.89%

Plants that contains it

• Senecio mairetianus

Cross-Links

• PubChem: 16091628
• LOTUS: LTS0160701
• wikiData: Q105121891