(1S,4S,4aS,6S,8aS)-1,4-dihydroxy-6,8a-dimethyl-5-methylene-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde

Details

• Internal ID: a831c229-40bc-4cd2-b636-c6668d632f3c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1S,4S,4aS,6S,8aS)-1,4-dihydroxy-6,8a-dimethyl-5-methylidene-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde
• SMILES (Canonical): CC1CCC2(C(C1=C)C(C=C(C2(C=O)O)C=O)O)C
• SMILES (Isomeric): C[C@H]1CC[C@]2([C@H](C1=C)[C@H](C=C([C@@]2(C=O)O)C=O)O)C
• InChI: InChI=1S/C15H20O4/c1-9-4-5-14(3)13(10(9)2)12(18)6-11(7-16)15(14,19)8-17/h6-9,12-13,18-19H,2,4-5H2,1,3H3/t9-,12-,13+,14-,15+/m0/s1
• InChI Key: LFSPEOPTWSAZEP-FRDLFTECSA-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): 74.60 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.02
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• (1S,4S,4aS,6S,8aS)-1,4-dihydroxy-6,8a-dimethyl-5-methylene-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9850	98.50%
Caco-2	-	0.5483	54.83%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7576	75.76%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.7989	79.89%
OATP1B3 inhibitior	+	0.9087	90.87%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6518	65.18%
BSEP inhibitior	-	0.9413	94.13%
P-glycoprotein inhibitior	-	0.9485	94.85%
P-glycoprotein substrate	-	0.8342	83.42%
CYP3A4 substrate	+	0.6187	61.87%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.8550	85.50%
CYP3A4 inhibition	-	0.7460	74.60%
CYP2C9 inhibition	-	0.7718	77.18%
CYP2C19 inhibition	-	0.8899	88.99%
CYP2D6 inhibition	-	0.8336	83.36%
CYP1A2 inhibition	-	0.7456	74.56%
CYP2C8 inhibition	-	0.6622	66.22%
CYP inhibitory promiscuity	-	0.8376	83.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9411	94.11%
Carcinogenicity (trinary)	Non-required	0.5722	57.22%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.9342	93.42%
Skin irritation	+	0.5104	51.04%
Skin corrosion	-	0.8613	86.13%
Ames mutagenesis	-	0.6423	64.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.6193	61.93%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5306	53.06%
skin sensitisation	-	0.5480	54.80%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4939	49.39%
Acute Oral Toxicity (c)	III	0.5104	51.04%
Estrogen receptor binding	-	0.5591	55.91%
Androgen receptor binding	+	0.5247	52.47%
Thyroid receptor binding	-	0.6117	61.17%
Glucocorticoid receptor binding	-	0.4885	48.85%
Aromatase binding	+	0.6221	62.21%
PPAR gamma	-	0.7066	70.66%
Honey bee toxicity	-	0.8523	85.23%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9920	99.20%

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	94.20%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.77%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.30%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.08%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.71%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	83.67%	94.75%
CHEMBL2581	P07339	Cathepsin D	83.07%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.77%	97.25%

Plants that contains it

• Warburgia ugandensis

Cross-Links

• PubChem: 11587024
• LOTUS: LTS0182518
• wikiData: Q105151160