methyl (1R,4aS,5R,7S,7aS)-1,5,7-trihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: ba8b4571-985c-4bfb-82f5-8467bcf673ee
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: methyl (1R,4aS,5R,7S,7aS)-1,5,7-trihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(CC(C2C1C(OC=C2C(=O)OC)O)O)O
• SMILES (Isomeric): C[C@@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O)O)O
• InChI: InChI=1S/C11H16O6/c1-11(15)3-6(12)7-5(9(13)16-2)4-17-10(14)8(7)11/h4,6-8,10,12,14-15H,3H2,1-2H3/t6-,7+,8-,10-,11+/m1/s1
• InChI Key: GGZSQSUXBPYCHQ-BEBVASNESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆O₆
• Molecular Weight: 244.24 g/mol
• Exact Mass: 244.09468823 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.86
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9231	92.31%
Caco-2	-	0.7201	72.01%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5047	50.47%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8988	89.88%
OATP1B3 inhibitior	+	0.9561	95.61%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9656	96.56%
P-glycoprotein inhibitior	-	0.9328	93.28%
P-glycoprotein substrate	-	0.8063	80.63%
CYP3A4 substrate	+	0.5853	58.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8580	85.80%
CYP3A4 inhibition	-	0.6436	64.36%
CYP2C9 inhibition	-	0.8708	87.08%
CYP2C19 inhibition	-	0.8059	80.59%
CYP2D6 inhibition	-	0.8735	87.35%
CYP1A2 inhibition	-	0.7780	77.80%
CYP2C8 inhibition	-	0.8350	83.50%
CYP inhibitory promiscuity	-	0.8129	81.29%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9219	92.19%
Carcinogenicity (trinary)	Non-required	0.5122	51.22%
Eye corrosion	-	0.9743	97.43%
Eye irritation	-	0.9630	96.30%
Skin irritation	-	0.6363	63.63%
Skin corrosion	-	0.9226	92.26%
Ames mutagenesis	+	0.5963	59.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6305	63.05%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7520	75.20%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6462	64.62%
Acute Oral Toxicity (c)	III	0.3497	34.97%
Estrogen receptor binding	+	0.5789	57.89%
Androgen receptor binding	-	0.6571	65.71%
Thyroid receptor binding	-	0.4909	49.09%
Glucocorticoid receptor binding	-	0.7894	78.94%
Aromatase binding	-	0.8701	87.01%
PPAR gamma	-	0.8008	80.08%
Honey bee toxicity	-	0.8696	86.96%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.5546	55.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.95%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.26%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.37%	85.14%
CHEMBL4208	P20618	Proteasome component C5	86.57%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.96%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.87%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	82.97%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.30%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.90%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.68%	95.89%

Plants that contains it

• Phlomoides rotata

Cross-Links

• PubChem: 25026345
• LOTUS: LTS0100806
• wikiData: Q105008393