5-[5-Hydroxy-3-(hydroxymethyl)pent-3-enyl]-1,4a,6-trimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: e28e049d-8b59-43ab-ae55-cd1b8fb257a3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 5-[5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-1,4a,6-trimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CCC2C(C1CCC(=CCO)CO)(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): CC1=CCC2C(C1CCC(=CCO)CO)(CCCC2(C)C(=O)O)C
• InChI: InChI=1S/C20H32O4/c1-14-5-8-17-19(2,10-4-11-20(17,3)18(23)24)16(14)7-6-15(13-22)9-12-21/h5,9,16-17,21-22H,4,6-8,10-13H2,1-3H3,(H,23,24)
• InChI Key: NVNBXFPYJOINAR-UHFFFAOYSA-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: 3.10
• 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	+	0.9741	97.41%
Caco-2	+	0.7313	73.13%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6893	68.93%
OATP2B1 inhibitior	-	0.8654	86.54%
OATP1B1 inhibitior	+	0.7716	77.16%
OATP1B3 inhibitior	-	0.2432	24.32%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5285	52.85%
BSEP inhibitior	+	0.7706	77.06%
P-glycoprotein inhibitior	-	0.8459	84.59%
P-glycoprotein substrate	-	0.7580	75.80%
CYP3A4 substrate	+	0.6106	61.06%
CYP2C9 substrate	-	0.6197	61.97%
CYP2D6 substrate	-	0.8732	87.32%
CYP3A4 inhibition	-	0.7348	73.48%
CYP2C9 inhibition	-	0.8087	80.87%
CYP2C19 inhibition	-	0.8462	84.62%
CYP2D6 inhibition	-	0.9036	90.36%
CYP1A2 inhibition	-	0.8526	85.26%
CYP2C8 inhibition	-	0.6345	63.45%
CYP inhibitory promiscuity	-	0.7577	75.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6602	66.02%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.8964	89.64%
Skin irritation	-	0.7752	77.52%
Skin corrosion	-	0.9830	98.30%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5083	50.83%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.7015	70.15%
skin sensitisation	-	0.6082	60.82%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6410	64.10%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7340	73.40%
Acute Oral Toxicity (c)	III	0.5403	54.03%
Estrogen receptor binding	+	0.6836	68.36%
Androgen receptor binding	-	0.5301	53.01%
Thyroid receptor binding	+	0.6632	66.32%
Glucocorticoid receptor binding	+	0.7931	79.31%
Aromatase binding	+	0.6926	69.26%
PPAR gamma	+	0.6245	62.45%
Honey bee toxicity	-	0.9308	93.08%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
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	93.11%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.39%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.63%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.63%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.14%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.20%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.24%	97.25%
CHEMBL2581	P07339	Cathepsin D	82.24%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.04%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.32%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.11%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.25%	93.00%

Plants that contains it

• Gutierrezia resinosa

Cross-Links

• PubChem: 162848675
• LOTUS: LTS0255121
• wikiData: Q105186328