(2E)-5-[(1R,2R,4aR,5R,8aS)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 05f788ae-ff4a-4ee0-b210-1773ed8e113a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1R,2R,4aR,5R,8aS)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
• SMILES (Canonical): CC(=CC(=O)O)CCC1C2(CCCC(C2CCC1(C)O)(C)CO)C
• SMILES (Isomeric): C/C(=C\C(=O)O)/CC[C@@H]1[C@]2(CCC[C@@]([C@@H]2CC[C@@]1(C)O)(C)CO)C
• InChI: InChI=1S/C20H34O4/c1-14(12-17(22)23)6-7-16-19(3)10-5-9-18(2,13-21)15(19)8-11-20(16,4)24/h12,15-16,21,24H,5-11,13H2,1-4H3,(H,22,23)/b14-12+/t15-,16+,18-,19-,20+/m0/s1
• InChI Key: IYSBWLRXTOIYFZ-KBLZDMJYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.50 g/mol
• Exact Mass: 338.24570956 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.76
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 8alpha-19-dihydroxylabd-13E-ene-15-oic acid
• (2E)-5-[(1R,2R,4aR,5R,8aS)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
• CHEMBL507405
• PD183250
• 8alpha,19-dihydroxylabd-13E-ene-15-oic acid
• Q27134279
• (E)-5-[(1R,2R,4aR,5R,8aS)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9907	99.07%
Caco-2	+	0.5473	54.73%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8378	83.78%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8031	80.31%
OATP1B3 inhibitior	+	0.8559	85.59%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5173	51.73%
BSEP inhibitior	+	0.6862	68.62%
P-glycoprotein inhibitior	-	0.8517	85.17%
P-glycoprotein substrate	-	0.8272	82.72%
CYP3A4 substrate	+	0.6117	61.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9209	92.09%
CYP3A4 inhibition	-	0.6323	63.23%
CYP2C9 inhibition	-	0.9251	92.51%
CYP2C19 inhibition	-	0.9480	94.80%
CYP2D6 inhibition	-	0.9335	93.35%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	-	0.6698	66.98%
CYP inhibitory promiscuity	-	0.8946	89.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7033	70.33%
Eye corrosion	-	0.9953	99.53%
Eye irritation	-	0.8324	83.24%
Skin irritation	+	0.5357	53.57%
Skin corrosion	-	0.9760	97.60%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3978	39.78%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7976	79.76%
skin sensitisation	-	0.8116	81.16%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7368	73.68%
Acute Oral Toxicity (c)	III	0.7891	78.91%
Estrogen receptor binding	+	0.8221	82.21%
Androgen receptor binding	+	0.5374	53.74%
Thyroid receptor binding	+	0.5878	58.78%
Glucocorticoid receptor binding	+	0.7250	72.50%
Aromatase binding	+	0.7292	72.92%
PPAR gamma	+	0.7246	72.46%
Honey bee toxicity	-	0.8901	89.01%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9880	98.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	94.70%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.44%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.90%	96.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.63%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	88.09%	91.19%
CHEMBL2061	P19793	Retinoid X receptor alpha	87.89%	91.67%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.17%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.76%	94.45%
CHEMBL206	P03372	Estrogen receptor alpha	82.65%	97.64%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.58%	96.38%
CHEMBL2581	P07339	Cathepsin D	82.32%	98.95%
CHEMBL233	P35372	Mu opioid receptor	81.86%	97.93%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.58%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.26%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.23%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.01%	92.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.39%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.37%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.01%	91.24%

Plants that contains it

• Acmella ciliata
• Solanecio mannii

Cross-Links

• PubChem: 24899923
• LOTUS: LTS0205548
• wikiData: Q105216187