(Z)-5-[(1S,4aR,8aR)-2-formyl-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid

Details

• Internal ID: d37357bf-b52a-40ed-843a-09b05748d3d7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-5-[(1S,4aR,8aR)-2-formyl-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(hydroxymethyl)pent-2-enoic acid
• SMILES (Canonical): CC1(CCCC2(C1CC=C(C2CCC(=CC(=O)O)CO)C=O)C)C
• SMILES (Isomeric): C[C@@]12CCCC([C@H]1CC=C([C@H]2CC/C(=C/C(=O)O)/CO)C=O)(C)C
• InChI: InChI=1S/C20H30O4/c1-19(2)9-4-10-20(3)16(15(13-22)6-8-17(19)20)7-5-14(12-21)11-18(23)24/h6,11,13,16-17,21H,4-5,7-10,12H2,1-3H3,(H,23,24)/b14-11-/t16-,17-,20+/m1/s1
• InChI Key: NYVSMUINRJWNRV-WOMDGJDESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.75
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9823	98.23%
Caco-2	+	0.5634	56.34%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8161	81.61%
OATP2B1 inhibitior	-	0.8655	86.55%
OATP1B1 inhibitior	+	0.7651	76.51%
OATP1B3 inhibitior	-	0.3769	37.69%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5453	54.53%
BSEP inhibitior	+	0.6668	66.68%
P-glycoprotein inhibitior	-	0.6879	68.79%
P-glycoprotein substrate	-	0.7204	72.04%
CYP3A4 substrate	+	0.6025	60.25%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.9097	90.97%
CYP3A4 inhibition	-	0.6883	68.83%
CYP2C9 inhibition	-	0.7977	79.77%
CYP2C19 inhibition	-	0.8848	88.48%
CYP2D6 inhibition	-	0.9205	92.05%
CYP1A2 inhibition	-	0.8780	87.80%
CYP2C8 inhibition	-	0.6056	60.56%
CYP inhibitory promiscuity	-	0.7268	72.68%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6942	69.42%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9302	93.02%
Skin irritation	-	0.7247	72.47%
Skin corrosion	-	0.9789	97.89%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3841	38.41%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7101	71.01%
skin sensitisation	+	0.6468	64.68%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6521	65.21%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6496	64.96%
Acute Oral Toxicity (c)	III	0.5781	57.81%
Estrogen receptor binding	+	0.7086	70.86%
Androgen receptor binding	+	0.5467	54.67%
Thyroid receptor binding	+	0.6003	60.03%
Glucocorticoid receptor binding	+	0.7694	76.94%
Aromatase binding	+	0.6117	61.17%
PPAR gamma	+	0.8045	80.45%
Honey bee toxicity	-	0.8918	89.18%
Biodegradation	-	0.8500	85.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.94%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.99%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.56%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.28%	94.62%
CHEMBL2581	P07339	Cathepsin D	85.81%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.24%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.22%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.91%	95.50%
CHEMBL233	P35372	Mu opioid receptor	82.53%	97.93%
CHEMBL5028	O14672	ADAM10	82.10%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.45%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.36%	94.45%

Plants that contains it

• Acritopappus confertus

Cross-Links

• PubChem: 162957988
• LOTUS: LTS0258126
• wikiData: Q105187727