ent-3beta,18-Dihydroxylabda-8(17),13E-dien-15-oic acid

Details

• Internal ID: 517c5fd5-a088-4473-9ef5-89750a731280
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1R,4aS,5S,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-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(CCC(C2(C)CO)O)C
• SMILES (Isomeric): C/C(=C\C(=O)O)/CC[C@@H]1C(=C)CC[C@H]2[C@]1(CC[C@H]([C@]2(C)CO)O)C
• InChI: InChI=1S/C20H32O4/c1-13(11-18(23)24)5-7-15-14(2)6-8-16-19(15,3)10-9-17(22)20(16,4)12-21/h11,15-17,21-22H,2,5-10,12H2,1,3-4H3,(H,23,24)/b13-11+/t15-,16+,17-,19+,20-/m1/s1
• InChI Key: TUWYNYPQCCGTMJ-PLGAWEPZSA-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: 4.10
• Atomic LogP (AlogP): 3.54
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• ent-3beta,18-Dihydroxylabda-8(17),13E-dien-15-oic acid
• AKOS040761669

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9748	97.48%
Caco-2	+	0.6583	65.83%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7139	71.39%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8902	89.02%
OATP1B3 inhibitior	-	0.3114	31.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5894	58.94%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.8170	81.70%
P-glycoprotein substrate	-	0.7511	75.11%
CYP3A4 substrate	+	0.6555	65.55%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9065	90.65%
CYP3A4 inhibition	-	0.7361	73.61%
CYP2C9 inhibition	-	0.8552	85.52%
CYP2C19 inhibition	-	0.8902	89.02%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.8765	87.65%
CYP2C8 inhibition	-	0.6644	66.44%
CYP inhibitory promiscuity	-	0.9132	91.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7123	71.23%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.7307	73.07%
Skin irritation	+	0.5298	52.98%
Skin corrosion	-	0.9622	96.22%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7274	72.74%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.8101	81.01%
skin sensitisation	-	0.8497	84.97%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4612	46.12%
Acute Oral Toxicity (c)	III	0.6533	65.33%
Estrogen receptor binding	+	0.7438	74.38%
Androgen receptor binding	+	0.7265	72.65%
Thyroid receptor binding	+	0.6665	66.65%
Glucocorticoid receptor binding	+	0.7810	78.10%
Aromatase binding	+	0.6098	60.98%
PPAR gamma	+	0.6101	61.01%
Honey bee toxicity	-	0.8521	85.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9917	99.17%

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	97.62%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.60%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	87.81%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.38%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.64%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.35%	95.50%
CHEMBL2061	P19793	Retinoid X receptor alpha	83.36%	91.67%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.58%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.83%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	81.46%	91.19%
CHEMBL5028	O14672	ADAM10	80.44%	97.50%

Plants that contains it

• Gutierrezia solbrigii

Cross-Links

• PubChem: 124708114
• LOTUS: LTS0046881
• wikiData: Q105265091