1-[5-Hydroxy-3-(hydroxymethyl)pent-3-enyl]-1,4a,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalene-2-carboxylic acid

Details

• Internal ID: 76503898-e02b-4735-9870-1cca4df7b390
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: 1-[5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-1,4a,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalene-2-carboxylic acid
• SMILES (Canonical): CC1=CCCC2C1(CCC(C2(C)CCC(=CCO)CO)C(=O)O)C
• SMILES (Isomeric): CC1=CCCC2C1(CCC(C2(C)CCC(=CCO)CO)C(=O)O)C
• InChI: InChI=1S/C20H32O4/c1-14-5-4-6-17-19(14,2)11-8-16(18(23)24)20(17,3)10-7-15(13-22)9-12-21/h5,9,16-17,21-22H,4,6-8,10-13H2,1-3H3,(H,23,24)
• InChI Key: CARVBZGFRUGPHE-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: 3.30
• 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	+	0.6971	69.71%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6893	68.93%
OATP2B1 inhibitior	-	0.8637	86.37%
OATP1B1 inhibitior	+	0.9077	90.77%
OATP1B3 inhibitior	-	0.2432	24.32%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5285	52.85%
BSEP inhibitior	+	0.8037	80.37%
P-glycoprotein inhibitior	-	0.7941	79.41%
P-glycoprotein substrate	-	0.7890	78.90%
CYP3A4 substrate	+	0.6097	60.97%
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	-	0.6082	60.82%
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	-	0.9313	93.13%
Skin irritation	-	0.7752	77.52%
Skin corrosion	-	0.9830	98.30%
Ames mutagenesis	-	0.6737	67.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4130	41.30%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.6082	60.82%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6410	64.10%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6485	64.85%
Acute Oral Toxicity (c)	III	0.5403	54.03%
Estrogen receptor binding	+	0.8058	80.58%
Androgen receptor binding	+	0.5923	59.23%
Thyroid receptor binding	+	0.6563	65.63%
Glucocorticoid receptor binding	+	0.7434	74.34%
Aromatase binding	+	0.6755	67.55%
PPAR gamma	+	0.6251	62.51%
Honey bee toxicity	-	0.9272	92.72%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
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	91.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.20%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.11%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.89%	93.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.75%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.51%	100.00%
CHEMBL5028	O14672	ADAM10	84.44%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.25%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.46%	97.25%
CHEMBL2581	P07339	Cathepsin D	81.96%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.69%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.64%	93.56%

Plants that contains it

• Baccharis boliviensis

Cross-Links

• PubChem: 163103629
• LOTUS: LTS0015931
• wikiData: Q104951842