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

Details

• Internal ID: 39a699d1-3419-4817-a9a2-b6dbc6d59014
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S,4aS,5S,8aS,9aS)-8a,9a-dihydroxy-4-methoxy-3,4a,5-trimethyl-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C16H24O5/c1-9-6-5-7-15(18)8-16(19)11(10(2)13(17)21-16)12(20-4)14(9,15)3/h9,12,18-19H,5-8H2,1-4H3/t9-,12+,14-,15-,16-/m0/s1
• InChI Key: KIJIXRMZCFRLDC-KTBXZTKVSA-N
• Popularity: 2 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	+	0.9860	98.60%
Caco-2	+	0.8165	81.65%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6985	69.85%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9023	90.23%
OATP1B3 inhibitior	+	0.9078	90.78%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	-	0.8697	86.97%
P-glycoprotein inhibitior	-	0.8778	87.78%
P-glycoprotein substrate	-	0.8907	89.07%
CYP3A4 substrate	+	0.6415	64.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8816	88.16%
CYP3A4 inhibition	-	0.6492	64.92%
CYP2C9 inhibition	-	0.8021	80.21%
CYP2C19 inhibition	-	0.8673	86.73%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	-	0.6223	62.23%
CYP2C8 inhibition	-	0.7030	70.30%
CYP inhibitory promiscuity	-	0.8293	82.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5161	51.61%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.7258	72.58%
Skin irritation	+	0.5368	53.68%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6121	61.21%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5364	53.64%
skin sensitisation	-	0.8460	84.60%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.6027	60.27%
Acute Oral Toxicity (c)	I	0.4024	40.24%
Estrogen receptor binding	+	0.7358	73.58%
Androgen receptor binding	+	0.6560	65.60%
Thyroid receptor binding	+	0.7095	70.95%
Glucocorticoid receptor binding	+	0.5691	56.91%
Aromatase binding	-	0.5238	52.38%
PPAR gamma	-	0.5289	52.89%
Honey bee toxicity	-	0.8224	82.24%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9810	98.10%

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	94.64%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.48%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.51%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	88.31%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.23%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.04%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.77%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.70%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.39%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.96%	93.03%
CHEMBL2581	P07339	Cathepsin D	83.85%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.89%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.98%	99.23%

Plants that contains it

• Parasenecio roborowskii

Cross-Links

• PubChem: 15840704
• LOTUS: LTS0027779
• wikiData: Q105141540