(1aS,6R,6aR,7S,7aS)-7-(2-hydroxypropan-2-yl)-6,6a-dimethyl-5,6,7,7a-tetrahydro-1aH-naphtho[2,3-b]oxirene-2,4-dione

Details

• Internal ID: 6456a1db-7579-45aa-a82e-32d89aed0109
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1aS,6R,6aR,7S,7aS)-7-(2-hydroxypropan-2-yl)-6,6a-dimethyl-5,6,7,7a-tetrahydro-1aH-naphtho[2,3-b]oxirene-2,4-dione
• SMILES (Canonical): CC1CC(=O)C=C2C1(C(C3C(C2=O)O3)C(C)(C)O)C
• SMILES (Isomeric): C[C@@H]1CC(=O)C=C2[C@]1([C@@H]([C@H]3[C@@H](C2=O)O3)C(C)(C)O)C
• InChI: InChI=1S/C15H20O4/c1-7-5-8(16)6-9-10(17)11-12(19-11)13(14(2,3)18)15(7,9)4/h6-7,11-13,18H,5H2,1-4H3/t7-,11-,12-,13+,15+/m1/s1
• InChI Key: GYTISTMGTHKMCE-RMHXPDDSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.90 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.27
• H-Bond Acceptor: 4
• 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	+	0.9937	99.37%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6481	64.81%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8864	88.64%
OATP1B3 inhibitior	+	0.9668	96.68%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9454	94.54%
P-glycoprotein inhibitior	-	0.8189	81.89%
P-glycoprotein substrate	-	0.8353	83.53%
CYP3A4 substrate	+	0.5679	56.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	-	0.8093	80.93%
CYP2C9 inhibition	-	0.8561	85.61%
CYP2C19 inhibition	-	0.8247	82.47%
CYP2D6 inhibition	-	0.8951	89.51%
CYP1A2 inhibition	-	0.8226	82.26%
CYP2C8 inhibition	-	0.9260	92.60%
CYP inhibitory promiscuity	-	0.8788	87.88%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5255	52.55%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9138	91.38%
Skin irritation	-	0.5739	57.39%
Skin corrosion	-	0.9114	91.14%
Ames mutagenesis	-	0.7127	71.27%
Human Ether-a-go-go-Related Gene inhibition	-	0.5089	50.89%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.5844	58.44%
skin sensitisation	-	0.6032	60.32%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5746	57.46%
Acute Oral Toxicity (c)	III	0.4643	46.43%
Estrogen receptor binding	+	0.6050	60.50%
Androgen receptor binding	+	0.5944	59.44%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5702	57.02%
Aromatase binding	-	0.6409	64.09%
PPAR gamma	-	0.6198	61.98%
Honey bee toxicity	-	0.8159	81.59%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9671	96.71%

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	97.02%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.58%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.06%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.20%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.35%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.19%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.46%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.11%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.01%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.75%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.57%	85.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.99%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.04%	86.33%

Plants that contains it

• Nardostachys jatamansi

Cross-Links

• PubChem: 14164976
• LOTUS: LTS0237660
• wikiData: Q105024145