(1R,2S,3S)-2-[(2R)-butan-2-yl]-2,3-dihydroxy-3-methyl-5-methylidene-4-oxocyclopentane-1-carboxylic acid

Details

• Internal ID: 6d7df123-71c3-4bfe-8d11-be8eb6745abb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Monocyclic monoterpenoids
• IUPAC Name: (1R,2S,3S)-2-[(2R)-butan-2-yl]-2,3-dihydroxy-3-methyl-5-methylidene-4-oxocyclopentane-1-carboxylic acid
• SMILES (Canonical): CCC(C)C1(C(C(=C)C(=O)C1(C)O)C(=O)O)O
• SMILES (Isomeric): CC[C@@H](C)[C@@]1([C@@H](C(=C)C(=O)[C@@]1(C)O)C(=O)O)O
• InChI: InChI=1S/C12H18O5/c1-5-6(2)12(17)8(10(14)15)7(3)9(13)11(12,4)16/h6,8,16-17H,3,5H2,1-2,4H3,(H,14,15)/t6-,8+,11-,12+/m1/s1
• InChI Key: HOGXTIRQAZXVHU-ONUNSANNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₈O₅
• Molecular Weight: 242.27 g/mol
• Exact Mass: 242.11542367 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8351	83.51%
Caco-2	-	0.6770	67.70%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6134	61.34%
OATP2B1 inhibitior	-	0.8506	85.06%
OATP1B1 inhibitior	+	0.8704	87.04%
OATP1B3 inhibitior	+	0.9274	92.74%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9407	94.07%
P-glycoprotein inhibitior	-	0.9196	91.96%
P-glycoprotein substrate	-	0.9169	91.69%
CYP3A4 substrate	-	0.5579	55.79%
CYP2C9 substrate	+	0.6171	61.71%
CYP2D6 substrate	-	0.8991	89.91%
CYP3A4 inhibition	-	0.7963	79.63%
CYP2C9 inhibition	-	0.7623	76.23%
CYP2C19 inhibition	-	0.7800	78.00%
CYP2D6 inhibition	-	0.9025	90.25%
CYP1A2 inhibition	-	0.8604	86.04%
CYP2C8 inhibition	-	0.9282	92.82%
CYP inhibitory promiscuity	-	0.8926	89.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8766	87.66%
Carcinogenicity (trinary)	Non-required	0.5954	59.54%
Eye corrosion	-	0.9800	98.00%
Eye irritation	-	0.8718	87.18%
Skin irritation	-	0.5838	58.38%
Skin corrosion	-	0.8919	89.19%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6083	60.83%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6139	61.39%
skin sensitisation	-	0.6051	60.51%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4597	45.97%
Estrogen receptor binding	+	0.7291	72.91%
Androgen receptor binding	+	0.5261	52.61%
Thyroid receptor binding	-	0.5944	59.44%
Glucocorticoid receptor binding	-	0.7580	75.80%
Aromatase binding	-	0.6307	63.07%
PPAR gamma	-	0.4849	48.49%
Honey bee toxicity	-	0.9536	95.36%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9865	98.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.90%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.08%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.95%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.01%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.45%	96.47%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.31%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	85.28%	90.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.36%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.77%	95.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163109395
• LOTUS: LTS0033935
• wikiData: Q105031272