(1S,4aR,5S,8aR)-5-[2-(furan-3-yl)-2-oxoethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 1e5d21c5-b363-40b8-9d38-3144bd03550b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (1S,4aR,5S,8aR)-5-[2-(furan-3-yl)-2-oxoethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC(=C)C2CC(=O)C3=COC=C3)(C)C(=O)O
• SMILES (Isomeric): C[C@]12CCC[C@]([C@@H]1CCC(=C)[C@@H]2CC(=O)C3=COC=C3)(C)C(=O)O
• InChI: InChI=1S/C20H26O4/c1-13-5-6-17-19(2,8-4-9-20(17,3)18(22)23)15(13)11-16(21)14-7-10-24-12-14/h7,10,12,15,17H,1,4-6,8-9,11H2,2-3H3,(H,22,23)/t15-,17+,19+,20-/m0/s1
• InChI Key: UWQHIMAXZZEVJA-ZSXHRAQDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 67.50 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.72
• H-Bond Acceptor: 3
• 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	+	0.9872	98.72%
Caco-2	+	0.6876	68.76%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6324	63.24%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	-	0.3466	34.66%
OATP1B3 inhibitior	-	0.2394	23.94%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6374	63.74%
BSEP inhibitior	-	0.7315	73.15%
P-glycoprotein inhibitior	-	0.7481	74.81%
P-glycoprotein substrate	-	0.7545	75.45%
CYP3A4 substrate	+	0.6136	61.36%
CYP2C9 substrate	+	0.6187	61.87%
CYP2D6 substrate	-	0.8746	87.46%
CYP3A4 inhibition	+	0.5559	55.59%
CYP2C9 inhibition	-	0.7879	78.79%
CYP2C19 inhibition	-	0.7714	77.14%
CYP2D6 inhibition	-	0.9446	94.46%
CYP1A2 inhibition	-	0.5364	53.64%
CYP2C8 inhibition	+	0.5363	53.63%
CYP inhibitory promiscuity	-	0.7390	73.90%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5979	59.79%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9350	93.50%
Skin irritation	-	0.5684	56.84%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.7670	76.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7875	78.75%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6740	67.40%
skin sensitisation	-	0.7457	74.57%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6181	61.81%
Acute Oral Toxicity (c)	III	0.3812	38.12%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5869	58.69%
Thyroid receptor binding	+	0.5623	56.23%
Glucocorticoid receptor binding	+	0.6453	64.53%
Aromatase binding	+	0.6903	69.03%
PPAR gamma	+	0.5984	59.84%
Honey bee toxicity	-	0.9264	92.64%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
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
CHEMBL221	P23219	Cyclooxygenase-1	93.90%	90.17%
CHEMBL4040	P28482	MAP kinase ERK2	92.69%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.79%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.30%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.27%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.35%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.45%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.58%	97.09%
CHEMBL5028	O14672	ADAM10	80.97%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.91%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.18%	89.00%

Plants that contains it

• Brickellia glomerata

Cross-Links

• PubChem: 162910384
• LOTUS: LTS0058769
• wikiData: Q105280494