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

Details

• Internal ID: 1fd071a8-25b3-41a4-ad74-28753060e7b2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aR,5R,8aR)-1,4a-dimethyl-5-[[(2S)-3-methyl-2,5-dihydrofuran-2-yl]methyl]-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CCOC1CC2C(=C)CCC3C2(CCCC3(C)C(=O)O)C
• SMILES (Isomeric): CC1=CCO[C@H]1C[C@@H]2C(=C)CC[C@@H]3[C@@]2(CCC[C@]3(C)C(=O)O)C
• InChI: InChI=1S/C20H30O3/c1-13-6-7-17-19(3,9-5-10-20(17,4)18(21)22)15(13)12-16-14(2)8-11-23-16/h8,15-17H,1,5-7,9-12H2,2-4H3,(H,21,22)/t15-,16+,17-,19-,20+/m1/s1
• InChI Key: FOFOBMPUEROEKT-DSJDWBEOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.59
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.7954	79.54%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6732	67.32%
OATP2B1 inhibitior	-	0.8649	86.49%
OATP1B1 inhibitior	+	0.8105	81.05%
OATP1B3 inhibitior	+	0.9055	90.55%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5648	56.48%
BSEP inhibitior	+	0.7665	76.65%
P-glycoprotein inhibitior	-	0.7261	72.61%
P-glycoprotein substrate	-	0.7928	79.28%
CYP3A4 substrate	+	0.6311	63.11%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	+	0.6038	60.38%
CYP2C9 inhibition	-	0.6517	65.17%
CYP2C19 inhibition	-	0.6671	66.71%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.6910	69.10%
CYP2C8 inhibition	+	0.4474	44.74%
CYP inhibitory promiscuity	-	0.6512	65.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6003	60.03%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.8798	87.98%
Skin irritation	-	0.5974	59.74%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6470	64.70%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6067	60.67%
skin sensitisation	-	0.7165	71.65%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7488	74.88%
Acute Oral Toxicity (c)	III	0.6653	66.53%
Estrogen receptor binding	+	0.7510	75.10%
Androgen receptor binding	-	0.4895	48.95%
Thyroid receptor binding	+	0.6359	63.59%
Glucocorticoid receptor binding	+	0.8415	84.15%
Aromatase binding	+	0.6410	64.10%
PPAR gamma	+	0.6596	65.96%
Honey bee toxicity	-	0.9183	91.83%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9966	99.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.65%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.46%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.19%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.24%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.18%	100.00%
CHEMBL5028	O14672	ADAM10	83.48%	97.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.92%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.72%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.34%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.76%	96.38%

Plants that contains it

• Chloranthus henryi

Cross-Links

• PubChem: 162991684
• LOTUS: LTS0005332
• wikiData: Q104912377