4-[(1R,2R,4R)-2-hydroxy-1-methyl-4-prop-1-en-2-ylcyclopentanecarbonyl]pent-4-enoic acid

Details

• Internal ID: c693bce7-5abc-4fbb-a54c-39a8589b566f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Monocyclic monoterpenoids
• IUPAC Name: 4-[(1R,2R,4R)-2-hydroxy-1-methyl-4-prop-1-en-2-ylcyclopentanecarbonyl]pent-4-enoic acid
• InChI: InChI=1S/C15H22O4/c1-9(2)11-7-12(16)15(4,8-11)14(19)10(3)5-6-13(17)18/h11-12,16H,1,3,5-8H2,2,4H3,(H,17,18)/t11-,12+,15+/m0/s1
• InChI Key: RTIKAOAEFATPRE-YWPYICTPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.33
• 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	+	0.9604	96.04%
Caco-2	+	0.5188	51.88%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7934	79.34%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.9149	91.49%
OATP1B3 inhibitior	+	0.8917	89.17%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6661	66.61%
BSEP inhibitior	-	0.8530	85.30%
P-glycoprotein inhibitior	-	0.9297	92.97%
P-glycoprotein substrate	-	0.7710	77.10%
CYP3A4 substrate	+	0.5424	54.24%
CYP2C9 substrate	-	0.6107	61.07%
CYP2D6 substrate	-	0.8905	89.05%
CYP3A4 inhibition	-	0.9180	91.80%
CYP2C9 inhibition	-	0.9002	90.02%
CYP2C19 inhibition	-	0.8938	89.38%
CYP2D6 inhibition	-	0.9415	94.15%
CYP1A2 inhibition	-	0.8996	89.96%
CYP2C8 inhibition	-	0.9262	92.62%
CYP inhibitory promiscuity	-	0.9765	97.65%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8628	86.28%
Carcinogenicity (trinary)	Non-required	0.6637	66.37%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.6542	65.42%
Skin irritation	+	0.5622	56.22%
Skin corrosion	-	0.9422	94.22%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6991	69.91%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5574	55.74%
skin sensitisation	-	0.7277	72.77%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6934	69.34%
Acute Oral Toxicity (c)	II	0.3552	35.52%
Estrogen receptor binding	-	0.5114	51.14%
Androgen receptor binding	-	0.7225	72.25%
Thyroid receptor binding	-	0.5338	53.38%
Glucocorticoid receptor binding	+	0.6376	63.76%
Aromatase binding	-	0.5428	54.28%
PPAR gamma	+	0.5598	55.98%
Honey bee toxicity	-	0.8466	84.66%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9937	99.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.00%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.59%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.25%	96.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.96%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.29%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	92.48%	83.82%
CHEMBL340	P08684	Cytochrome P450 3A4	89.43%	91.19%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.34%	97.21%
CHEMBL2581	P07339	Cathepsin D	86.23%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.08%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.10%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.80%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.42%	99.17%

Plants that contains it

• Artemisia alba

Cross-Links

• PubChem: 101958930
• LOTUS: LTS0148436
• wikiData: Q105245159