(2R,5S)-2-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-hydroxy-2,5-dihydrofuran-3-carboxylic acid

Details

• Internal ID: 10bf78e0-d5bc-4d01-93ca-e64705972f5f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (2R,5S)-2-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-hydroxy-2,5-dihydrofuran-3-carboxylic acid
• SMILES (Canonical): CC1(CCCC2(C1CCC(=C)C2CC3C(=CC(O3)O)C(=O)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CCC(=C)[C@@H]2C[C@@H]3C(=C[C@H](O3)O)C(=O)O)(C)C
• InChI: InChI=1S/C20H30O4/c1-12-6-7-16-19(2,3)8-5-9-20(16,4)14(12)11-15-13(18(22)23)10-17(21)24-15/h10,14-17,21H,1,5-9,11H2,2-4H3,(H,22,23)/t14-,15+,16-,17-,20+/m0/s1
• InChI Key: WMUHHECWRXDARQ-YPLULLRNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.90
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9822	98.22%
Caco-2	+	0.5495	54.95%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6280	62.80%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.8106	81.06%
OATP1B3 inhibitior	-	0.2529	25.29%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7581	75.81%
P-glycoprotein inhibitior	-	0.7592	75.92%
P-glycoprotein substrate	-	0.8600	86.00%
CYP3A4 substrate	+	0.6132	61.32%
CYP2C9 substrate	-	0.7936	79.36%
CYP2D6 substrate	-	0.9031	90.31%
CYP3A4 inhibition	-	0.6046	60.46%
CYP2C9 inhibition	-	0.8750	87.50%
CYP2C19 inhibition	-	0.7878	78.78%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.6175	61.75%
CYP2C8 inhibition	-	0.6208	62.08%
CYP inhibitory promiscuity	-	0.7600	76.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5657	56.57%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8809	88.09%
Skin irritation	+	0.6283	62.83%
Skin corrosion	-	0.9229	92.29%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4398	43.98%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5976	59.76%
skin sensitisation	-	0.7106	71.06%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6777	67.77%
Acute Oral Toxicity (c)	I	0.6081	60.81%
Estrogen receptor binding	+	0.8199	81.99%
Androgen receptor binding	+	0.5810	58.10%
Thyroid receptor binding	+	0.7399	73.99%
Glucocorticoid receptor binding	+	0.7941	79.41%
Aromatase binding	+	0.7427	74.27%
PPAR gamma	+	0.7206	72.06%
Honey bee toxicity	-	0.9020	90.20%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	97.41%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.64%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.48%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.66%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.65%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.64%	86.33%
CHEMBL2581	P07339	Cathepsin D	85.62%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.86%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.52%	94.45%
CHEMBL5028	O14672	ADAM10	82.28%	97.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.44%	96.38%

Plants that contains it

• Renealmia alpinia

Cross-Links

• PubChem: 163088768
• LOTUS: LTS0276203
• wikiData: Q105308851