(Z)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid

Details

• Internal ID: 598ed7c3-e11b-4f12-8d87-794e404fbd72
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid
• SMILES (Canonical): CC1(CCCC2(C1CC=C(C2CCC(=CC(=O)O)CO)CO)C)C
• SMILES (Isomeric): C[C@@]12CCCC([C@H]1CC=C([C@H]2CC/C(=C/C(=O)O)/CO)CO)(C)C
• InChI: InChI=1S/C20H32O4/c1-19(2)9-4-10-20(3)16(15(13-22)6-8-17(19)20)7-5-14(12-21)11-18(23)24/h6,11,16-17,21-22H,4-5,7-10,12-13H2,1-3H3,(H,23,24)/b14-11-/t16-,17-,20+/m1/s1
• InChI Key: RCTNNDKRYXNYTI-WOMDGJDESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.54
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9781	97.81%
Caco-2	+	0.5798	57.98%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7339	73.39%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.7997	79.97%
OATP1B3 inhibitior	-	0.3377	33.77%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5183	51.83%
BSEP inhibitior	-	0.5656	56.56%
P-glycoprotein inhibitior	-	0.8136	81.36%
P-glycoprotein substrate	-	0.7847	78.47%
CYP3A4 substrate	+	0.5966	59.66%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.9158	91.58%
CYP3A4 inhibition	-	0.8089	80.89%
CYP2C9 inhibition	-	0.7932	79.32%
CYP2C19 inhibition	-	0.8447	84.47%
CYP2D6 inhibition	-	0.9122	91.22%
CYP1A2 inhibition	-	0.8861	88.61%
CYP2C8 inhibition	-	0.6096	60.96%
CYP inhibitory promiscuity	-	0.7370	73.70%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6743	67.43%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.8823	88.23%
Skin irritation	-	0.7858	78.58%
Skin corrosion	-	0.9807	98.07%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3663	36.63%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6550	65.50%
skin sensitisation	+	0.5471	54.71%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6299	62.99%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7367	73.67%
Acute Oral Toxicity (c)	III	0.5033	50.33%
Estrogen receptor binding	+	0.6744	67.44%
Androgen receptor binding	+	0.6247	62.47%
Thyroid receptor binding	+	0.6392	63.92%
Glucocorticoid receptor binding	+	0.7269	72.69%
Aromatase binding	+	0.5834	58.34%
PPAR gamma	+	0.6835	68.35%
Honey bee toxicity	-	0.8626	86.26%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
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	95.44%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.37%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.31%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.94%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.31%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.55%	94.62%
CHEMBL2581	P07339	Cathepsin D	86.58%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.03%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.58%	100.00%
CHEMBL5028	O14672	ADAM10	80.40%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.03%	86.33%

Plants that contains it

• Acritopappus confertus

Cross-Links

• PubChem: 162914164
• LOTUS: LTS0062704
• wikiData: Q105233956