(1R,2S,3R,4R)-2,3,4-trihydroxy-3-methyl-5-methylidene-2-propan-2-ylcyclopentane-1-carboxylic acid

Details

• Internal ID: 412544d3-0b68-443e-a9e1-d4d668c9ae4d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: (1R,2S,3R,4R)-2,3,4-trihydroxy-3-methyl-5-methylidene-2-propan-2-ylcyclopentane-1-carboxylic acid
• SMILES (Canonical): CC(C)C1(C(C(=C)C(C1(C)O)O)C(=O)O)O
• SMILES (Isomeric): CC(C)[C@@]1([C@@H](C(=C)[C@H]([C@@]1(C)O)O)C(=O)O)O
• InChI: InChI=1S/C11H18O5/c1-5(2)11(16)7(9(13)14)6(3)8(12)10(11,4)15/h5,7-8,12,15-16H,3H2,1-2,4H3,(H,13,14)/t7-,8+,10+,11-/m0/s1
• InChI Key: WOKKVHZSRZBBBW-URPMGSGRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₈O₅
• Molecular Weight: 230.26 g/mol
• Exact Mass: 230.11542367 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9005	90.05%
Caco-2	-	0.8956	89.56%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7071	70.71%
OATP2B1 inhibitior	-	0.8514	85.14%
OATP1B1 inhibitior	+	0.9284	92.84%
OATP1B3 inhibitior	+	0.9373	93.73%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9555	95.55%
P-glycoprotein inhibitior	-	0.9262	92.62%
P-glycoprotein substrate	-	0.9353	93.53%
CYP3A4 substrate	-	0.5585	55.85%
CYP2C9 substrate	+	0.6045	60.45%
CYP2D6 substrate	-	0.8869	88.69%
CYP3A4 inhibition	-	0.8959	89.59%
CYP2C9 inhibition	-	0.7807	78.07%
CYP2C19 inhibition	-	0.8734	87.34%
CYP2D6 inhibition	-	0.9375	93.75%
CYP1A2 inhibition	-	0.8730	87.30%
CYP2C8 inhibition	-	0.9630	96.30%
CYP inhibitory promiscuity	-	0.9024	90.24%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.8323	83.23%
Carcinogenicity (trinary)	Non-required	0.6096	60.96%
Eye corrosion	-	0.9573	95.73%
Eye irritation	-	0.8368	83.68%
Skin irritation	-	0.5391	53.91%
Skin corrosion	-	0.8790	87.90%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7650	76.50%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5969	59.69%
Acute Oral Toxicity (c)	III	0.5089	50.89%
Estrogen receptor binding	-	0.5205	52.05%
Androgen receptor binding	+	0.5698	56.98%
Thyroid receptor binding	-	0.6444	64.44%
Glucocorticoid receptor binding	-	0.8308	83.08%
Aromatase binding	-	0.6225	62.25%
PPAR gamma	+	0.5970	59.70%
Honey bee toxicity	-	0.9076	90.76%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9532	95.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	90.52%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.51%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.40%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.04%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.83%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.66%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.95%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.71%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	80.42%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163114978
• LOTUS: LTS0077131
• wikiData: Q105309557