(1R,4aS,6S,8R,8aS)-8-hydroxy-6,8a-dimethyl-5-methylidene-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde

Details

• Internal ID: 84dfd8f9-4633-4e74-8583-29e94d68f2e1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1R,4aS,6S,8R,8aS)-8-hydroxy-6,8a-dimethyl-5-methylidene-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde
• SMILES (Canonical): CC1CC(C2(C(C1=C)CC=C(C2C=O)C=O)C)O
• SMILES (Isomeric): C[C@H]1C[C@H]([C@]2([C@H](C1=C)CC=C([C@@H]2C=O)C=O)C)O
• InChI: InChI=1S/C15H20O3/c1-9-6-14(18)15(3)12(10(9)2)5-4-11(7-16)13(15)8-17/h4,7-9,12-14,18H,2,5-6H2,1,3H3/t9-,12-,13-,14+,15-/m0/s1
• InChI Key: AKSBEXNBIJAHCH-MKJLKUPLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.91
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.7591	75.91%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6816	68.16%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8631	86.31%
OATP1B3 inhibitior	+	0.9532	95.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7552	75.52%
BSEP inhibitior	-	0.8837	88.37%
P-glycoprotein inhibitior	-	0.9395	93.95%
P-glycoprotein substrate	-	0.7624	76.24%
CYP3A4 substrate	+	0.5650	56.50%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.8618	86.18%
CYP3A4 inhibition	-	0.5736	57.36%
CYP2C9 inhibition	-	0.8795	87.95%
CYP2C19 inhibition	-	0.8263	82.63%
CYP2D6 inhibition	-	0.9108	91.08%
CYP1A2 inhibition	-	0.9029	90.29%
CYP2C8 inhibition	-	0.8800	88.00%
CYP inhibitory promiscuity	-	0.8814	88.14%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9013	90.13%
Carcinogenicity (trinary)	Non-required	0.5385	53.85%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8803	88.03%
Skin irritation	+	0.5589	55.89%
Skin corrosion	-	0.9202	92.02%
Ames mutagenesis	-	0.8164	81.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4157	41.57%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	+	0.5715	57.15%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5362	53.62%
Acute Oral Toxicity (c)	III	0.6609	66.09%
Estrogen receptor binding	-	0.6105	61.05%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.6497	64.97%
Glucocorticoid receptor binding	-	0.6832	68.32%
Aromatase binding	-	0.5664	56.64%
PPAR gamma	-	0.6126	61.26%
Honey bee toxicity	-	0.8134	81.34%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9925	99.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.58%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.12%	91.11%
CHEMBL1871	P10275	Androgen Receptor	88.69%	96.43%
CHEMBL221	P23219	Cyclooxygenase-1	88.18%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.89%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	87.80%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.91%	100.00%
CHEMBL2581	P07339	Cathepsin D	82.97%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.60%	86.33%
CHEMBL4208	P20618	Proteasome component C5	80.80%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.57%	97.09%

Plants that contains it

• Pseudowintera axillaris

Cross-Links

• PubChem: 11536109
• LOTUS: LTS0152574
• wikiData: Q104913819