(Z)-5-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid

Details

• Internal ID: 9925ae03-dfe1-423e-8914-cb55d185e501
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (Z)-5-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC(=CC(=O)O)CO)CCC=C2C)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC/C(=C/C(=O)O)/CO)CCC=C2C)C
• InChI: InChI=1S/C20H32O3/c1-14-6-5-7-17-19(14,3)10-8-15(2)20(17,4)11-9-16(13-21)12-18(22)23/h6,12,15,17,21H,5,7-11,13H2,1-4H3,(H,22,23)/b16-12-/t15-,17+,19+,20+/m1/s1
• InChI Key: RHULDSMZUNDRJY-DQLOYZPXSA-N
• Popularity: 1 reference 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: 4.90
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	+	0.7436	74.36%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	0.8659	86.59%
OATP1B1 inhibitior	+	0.8925	89.25%
OATP1B3 inhibitior	-	0.2274	22.74%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5741	57.41%
BSEP inhibitior	-	0.5294	52.94%
P-glycoprotein inhibitior	-	0.6405	64.05%
P-glycoprotein substrate	-	0.8280	82.80%
CYP3A4 substrate	+	0.5845	58.45%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.9158	91.58%
CYP3A4 inhibition	-	0.6882	68.82%
CYP2C9 inhibition	-	0.6578	65.78%
CYP2C19 inhibition	-	0.7964	79.64%
CYP2D6 inhibition	-	0.9042	90.42%
CYP1A2 inhibition	-	0.8061	80.61%
CYP2C8 inhibition	-	0.6439	64.39%
CYP inhibitory promiscuity	-	0.6529	65.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6282	62.82%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9100	91.00%
Skin irritation	-	0.7480	74.80%
Skin corrosion	-	0.9832	98.32%
Ames mutagenesis	-	0.6737	67.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3794	37.94%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5733	57.33%
skin sensitisation	-	0.5294	52.94%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7439	74.39%
Acute Oral Toxicity (c)	III	0.5748	57.48%
Estrogen receptor binding	+	0.8363	83.63%
Androgen receptor binding	+	0.6116	61.16%
Thyroid receptor binding	+	0.7372	73.72%
Glucocorticoid receptor binding	+	0.7628	76.28%
Aromatase binding	+	0.7585	75.85%
PPAR gamma	+	0.7227	72.27%
Honey bee toxicity	-	0.9073	90.73%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
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	92.78%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.50%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.09%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.70%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.76%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.39%	97.09%
CHEMBL5028	O14672	ADAM10	83.08%	97.50%
CHEMBL2581	P07339	Cathepsin D	82.49%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.06%	94.45%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162919417
• LOTUS: LTS0048022
• wikiData: Q105236625