(E)-5-[(1R,4aR,8aR)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid

Details

• Internal ID: ae73affe-81f6-45e5-8804-61b52a0c3804
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1R,4aR,8aR)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid
• SMILES (Canonical): CC1=CCC2C(CCCC2(C1CCC(=CC(=O)O)CO)C)(C)C
• SMILES (Isomeric): CC1=CC[C@H]2[C@]([C@@H]1CC/C(=C\C(=O)O)/CO)(CCCC2(C)C)C
• InChI: InChI=1S/C20H32O3/c1-14-6-9-17-19(2,3)10-5-11-20(17,4)16(14)8-7-15(13-21)12-18(22)23/h6,12,16-17,21H,5,7-11,13H2,1-4H3,(H,22,23)/b15-12+/t16-,17-,20+/m1/s1
• InChI Key: XZCAMMNTVAQDPZ-WITNYINYSA-N
• Popularity: 1 reference 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: 4.80
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9931	99.31%
Caco-2	+	0.6361	63.61%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7394	73.94%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8249	82.49%
OATP1B3 inhibitior	-	0.3107	31.07%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5593	55.93%
BSEP inhibitior	+	0.5803	58.03%
P-glycoprotein inhibitior	-	0.7907	79.07%
P-glycoprotein substrate	-	0.8207	82.07%
CYP3A4 substrate	+	0.5997	59.97%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.9158	91.58%
CYP3A4 inhibition	-	0.7748	77.48%
CYP2C9 inhibition	-	0.6508	65.08%
CYP2C19 inhibition	-	0.8003	80.03%
CYP2D6 inhibition	-	0.9134	91.34%
CYP1A2 inhibition	-	0.8583	85.83%
CYP2C8 inhibition	-	0.6079	60.79%
CYP inhibitory promiscuity	-	0.6120	61.20%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6433	64.33%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.8827	88.27%
Skin irritation	-	0.7506	75.06%
Skin corrosion	-	0.9810	98.10%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6600	66.00%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6726	67.26%
skin sensitisation	+	0.6136	61.36%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7894	78.94%
Acute Oral Toxicity (c)	III	0.5052	50.52%
Estrogen receptor binding	+	0.6915	69.15%
Androgen receptor binding	+	0.5460	54.60%
Thyroid receptor binding	+	0.6327	63.27%
Glucocorticoid receptor binding	+	0.7448	74.48%
Aromatase binding	+	0.5826	58.26%
PPAR gamma	+	0.8075	80.75%
Honey bee toxicity	-	0.9212	92.12%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.86%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.63%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.27%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.88%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.84%	94.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.27%	93.56%
CHEMBL2581	P07339	Cathepsin D	85.68%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.39%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.97%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.36%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.52%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.47%	97.09%
CHEMBL5028	O14672	ADAM10	80.27%	97.50%

Plants that contains it

• Acritopappus confertus

Cross-Links

• PubChem: 162903556
• LOTUS: LTS0160307
• wikiData: Q105344835