5-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)-3-methylpent-2-enoic acid

Details

• Internal ID: 38128abf-ce5e-49d0-9839-94e52f58e9a1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 5-(7-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)-3-methylpent-2-enoic acid
• SMILES (Canonical): CC(=CC(=O)O)CCC1C(=C)CCC2C1(CC(CC2(C)C)O)C
• SMILES (Isomeric): CC(=CC(=O)O)CCC1C(=C)CCC2C1(CC(CC2(C)C)O)C
• InChI: InChI=1S/C20H32O3/c1-13(10-18(22)23)6-8-16-14(2)7-9-17-19(3,4)11-15(21)12-20(16,17)5/h10,15-17,21H,2,6-9,11-12H2,1,3-5H3,(H,22,23)
• InChI Key: PUWSLGIIKGDKAD-UHFFFAOYSA-N
• Popularity: 0 references 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: 4.70
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.6664	66.64%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7510	75.10%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.8479	84.79%
OATP1B3 inhibitior	+	0.8813	88.13%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.6169	61.69%
P-glycoprotein inhibitior	-	0.7533	75.33%
P-glycoprotein substrate	-	0.7661	76.61%
CYP3A4 substrate	+	0.6054	60.54%
CYP2C9 substrate	-	0.7928	79.28%
CYP2D6 substrate	-	0.9050	90.50%
CYP3A4 inhibition	-	0.6888	68.88%
CYP2C9 inhibition	-	0.9199	91.99%
CYP2C19 inhibition	-	0.8698	86.98%
CYP2D6 inhibition	-	0.9474	94.74%
CYP1A2 inhibition	-	0.9215	92.15%
CYP2C8 inhibition	-	0.6224	62.24%
CYP inhibitory promiscuity	-	0.8365	83.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6870	68.70%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.8219	82.19%
Skin irritation	+	0.6283	62.83%
Skin corrosion	-	0.9611	96.11%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3901	39.01%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7726	77.26%
skin sensitisation	+	0.5696	56.96%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6031	60.31%
Acute Oral Toxicity (c)	III	0.6820	68.20%
Estrogen receptor binding	+	0.7548	75.48%
Androgen receptor binding	+	0.6507	65.07%
Thyroid receptor binding	+	0.6343	63.43%
Glucocorticoid receptor binding	+	0.7673	76.73%
Aromatase binding	+	0.6414	64.14%
PPAR gamma	+	0.7183	71.83%
Honey bee toxicity	-	0.8471	84.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9973	99.73%

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	96.56%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.32%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.47%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.14%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.02%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.84%	97.25%
CHEMBL2061	P19793	Retinoid X receptor alpha	82.99%	91.67%
CHEMBL2581	P07339	Cathepsin D	81.90%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	81.19%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.88%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.59%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.33%	95.50%

Plants that contains it

• Leiocarpa semicalva

Cross-Links

• PubChem: 162982294
• LOTUS: LTS0083776
• wikiData: Q105215332