5-[(1S,4aR,5R,6R,8aR)-5-hydroxy-5,6,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 636a25c4-6b9c-4ccb-a9d2-4eb5e511b6bb
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Medium-chain fatty acids
• IUPAC Name: 5-[(1S,4aR,5R,6R,8aR)-5-hydroxy-5,6,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)O)CCC(=C)C2CCC(=CC(=O)O)C)C
• SMILES (Isomeric): C[C@@H]1CC[C@]2([C@H]([C@]1(C)O)CCC(=C)[C@@H]2CCC(=CC(=O)O)C)C
• InChI: InChI=1S/C20H32O3/c1-13(12-18(21)22)6-8-16-14(2)7-9-17-19(16,4)11-10-15(3)20(17,5)23/h12,15-17,23H,2,6-11H2,1,3-5H3,(H,21,22)/t15-,16+,17-,19-,20-/m1/s1
• InChI Key: KKSRPYFDSRXBHV-JEIKXUOUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.7340	73.40%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7574	75.74%
OATP2B1 inhibitior	-	0.8635	86.35%
OATP1B1 inhibitior	+	0.8526	85.26%
OATP1B3 inhibitior	+	0.8213	82.13%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7014	70.14%
P-glycoprotein inhibitior	-	0.7448	74.48%
P-glycoprotein substrate	-	0.7824	78.24%
CYP3A4 substrate	+	0.6385	63.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9217	92.17%
CYP3A4 inhibition	-	0.6734	67.34%
CYP2C9 inhibition	-	0.7970	79.70%
CYP2C19 inhibition	-	0.7951	79.51%
CYP2D6 inhibition	-	0.9290	92.90%
CYP1A2 inhibition	-	0.8301	83.01%
CYP2C8 inhibition	-	0.6821	68.21%
CYP inhibitory promiscuity	-	0.7638	76.38%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6299	62.99%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8836	88.36%
Skin irritation	+	0.5392	53.92%
Skin corrosion	-	0.9665	96.65%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7303	73.03%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6351	63.51%
skin sensitisation	+	0.5605	56.05%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8452	84.52%
Acute Oral Toxicity (c)	III	0.7573	75.73%
Estrogen receptor binding	+	0.7653	76.53%
Androgen receptor binding	+	0.6296	62.96%
Thyroid receptor binding	+	0.7111	71.11%
Glucocorticoid receptor binding	+	0.7541	75.41%
Aromatase binding	+	0.6300	63.00%
PPAR gamma	+	0.7378	73.78%
Honey bee toxicity	-	0.8848	88.48%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	93.62%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.47%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	88.32%	90.17%
CHEMBL2061	P19793	Retinoid X receptor alpha	87.09%	91.67%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.06%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.98%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	84.93%	83.82%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.57%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.53%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.34%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.31%	91.19%

Plants that contains it

• Metasequoia glyptostroboides

Cross-Links

• PubChem: 163069463
• LOTUS: LTS0056037
• wikiData: Q105142346