(1S,4aS,5R,8aS)-1,4a-dimethyl-6-methylidene-5-[(2Z)-3-methylpenta-2,4-dienyl]-3-oxo-2,4,5,7,8,8a-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: 91a1eb86-dcf4-4892-904a-f23d6812fa1e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aS,5R,8aS)-1,4a-dimethyl-6-methylidene-5-[(2Z)-3-methylpenta-2,4-dienyl]-3-oxo-2,4,5,7,8,8a-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC(=CCC1C(=C)CCC2C1(CC(=O)CC2(C)C(=O)O)C)C=C
• SMILES (Isomeric): C/C(=C/C[C@@H]1C(=C)CC[C@H]2[C@]1(CC(=O)C[C@]2(C)C(=O)O)C)/C=C
• InChI: InChI=1S/C20H28O3/c1-6-13(2)7-9-16-14(3)8-10-17-19(16,4)11-15(21)12-20(17,5)18(22)23/h6-7,16-17H,1,3,8-12H2,2,4-5H3,(H,22,23)/b13-7-/t16-,17+,19+,20+/m1/s1
• InChI Key: JHPRIWZCNRYXGI-BCLYJQJYSA-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: 4.00
• 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	+	0.9934	99.34%
Caco-2	+	0.7009	70.09%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8336	83.36%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8836	88.36%
OATP1B3 inhibitior	+	0.8301	83.01%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6283	62.83%
P-glycoprotein inhibitior	-	0.8335	83.35%
P-glycoprotein substrate	-	0.7616	76.16%
CYP3A4 substrate	+	0.6380	63.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8844	88.44%
CYP3A4 inhibition	-	0.5731	57.31%
CYP2C9 inhibition	-	0.8832	88.32%
CYP2C19 inhibition	-	0.8343	83.43%
CYP2D6 inhibition	-	0.9548	95.48%
CYP1A2 inhibition	-	0.8948	89.48%
CYP2C8 inhibition	-	0.6920	69.20%
CYP inhibitory promiscuity	-	0.9139	91.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6288	62.88%
Eye corrosion	-	0.9937	99.37%
Eye irritation	-	0.9082	90.82%
Skin irritation	+	0.5985	59.85%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7694	76.94%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5518	55.18%
skin sensitisation	-	0.5383	53.83%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7277	72.77%
Acute Oral Toxicity (c)	III	0.7872	78.72%
Estrogen receptor binding	-	0.6007	60.07%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5278	52.78%
Glucocorticoid receptor binding	+	0.6049	60.49%
Aromatase binding	+	0.6473	64.73%
PPAR gamma	+	0.5421	54.21%
Honey bee toxicity	-	0.8724	87.24%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
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	93.98%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	89.18%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.75%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.25%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.45%	91.19%
CHEMBL2581	P07339	Cathepsin D	86.83%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	86.28%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.51%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.40%	93.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.88%	89.34%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.41%	100.00%

Plants that contains it

• Ichthyothere terminalis

Cross-Links

• PubChem: 163026611
• LOTUS: LTS0091593
• wikiData: Q105128150