(1S,4aS,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(1Z,3Z)-3-methyl-5-oxopenta-1,3-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 1d826b0d-ebd3-4c6f-8b00-ca74441ffa65
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aS,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(1Z,3Z)-3-methyl-5-oxopenta-1,3-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(=CC=O)C=CC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): C/C(=C/C=O)/C=C\[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C
• InChI: InChI=1S/C20H28O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h6,8,10,13,16-17H,2,5,7,9,11-12H2,1,3-4H3,(H,22,23)/b8-6-,14-10-/t16-,17+,19+,20-/m0/s1
• InChI Key: BIKTYBKSVBXGDW-GSXFEPPTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.55
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	+	0.7301	73.01%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6949	69.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8063	80.63%
OATP1B3 inhibitior	-	0.3510	35.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	+	0.8167	81.67%
P-glycoprotein inhibitior	-	0.7765	77.65%
P-glycoprotein substrate	-	0.7615	76.15%
CYP3A4 substrate	+	0.6226	62.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9086	90.86%
CYP3A4 inhibition	-	0.6950	69.50%
CYP2C9 inhibition	-	0.6581	65.81%
CYP2C19 inhibition	-	0.7013	70.13%
CYP2D6 inhibition	-	0.9391	93.91%
CYP1A2 inhibition	-	0.8304	83.04%
CYP2C8 inhibition	-	0.6499	64.99%
CYP inhibitory promiscuity	-	0.9092	90.92%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6165	61.65%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.9597	95.97%
Skin irritation	-	0.5429	54.29%
Skin corrosion	-	0.9704	97.04%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6881	68.81%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6104	61.04%
skin sensitisation	+	0.7965	79.65%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6162	61.62%
Acute Oral Toxicity (c)	III	0.7081	70.81%
Estrogen receptor binding	+	0.5987	59.87%
Androgen receptor binding	-	0.5492	54.92%
Thyroid receptor binding	+	0.6399	63.99%
Glucocorticoid receptor binding	+	0.6432	64.32%
Aromatase binding	+	0.6874	68.74%
PPAR gamma	-	0.4875	48.75%
Honey bee toxicity	-	0.8786	87.86%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	93.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.45%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.01%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.78%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.69%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.43%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.37%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.85%	95.50%

Plants that contains it

• Thuja standishii

Cross-Links

• PubChem: 21609747
• LOTUS: LTS0119538
• wikiData: Q104936577