Methyl 1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 5b47d93c-2951-42ad-af46-9b80fe412986
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: methyl 1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)OC)O)O
• SMILES (Isomeric): CC1C(CC2C1C(OC=C2C(=O)OC)O)O
• InChI: InChI=1S/C11H16O5/c1-5-8(12)3-6-7(10(13)15-2)4-16-11(14)9(5)6/h4-6,8-9,11-12,14H,3H2,1-2H3
• InChI Key: XWOHZIIPBYAMJX-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆O₅
• Molecular Weight: 228.24 g/mol
• Exact Mass: 228.09977361 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.03
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9664	96.64%
Caco-2	-	0.5607	56.07%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5634	56.34%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.7693	76.93%
OATP1B3 inhibitior	+	0.9618	96.18%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9640	96.40%
P-glycoprotein inhibitior	-	0.9572	95.72%
P-glycoprotein substrate	-	0.8145	81.45%
CYP3A4 substrate	+	0.5567	55.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8512	85.12%
CYP3A4 inhibition	-	0.7877	78.77%
CYP2C9 inhibition	-	0.8993	89.93%
CYP2C19 inhibition	-	0.8430	84.30%
CYP2D6 inhibition	-	0.8838	88.38%
CYP1A2 inhibition	-	0.6710	67.10%
CYP2C8 inhibition	-	0.7289	72.89%
CYP inhibitory promiscuity	-	0.8051	80.51%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9438	94.38%
Carcinogenicity (trinary)	Non-required	0.5845	58.45%
Eye corrosion	-	0.9751	97.51%
Eye irritation	-	0.9159	91.59%
Skin irritation	-	0.5906	59.06%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	+	0.5146	51.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.5542	55.42%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8153	81.53%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6684	66.84%
Acute Oral Toxicity (c)	I	0.3564	35.64%
Estrogen receptor binding	-	0.7486	74.86%
Androgen receptor binding	-	0.6440	64.40%
Thyroid receptor binding	-	0.5807	58.07%
Glucocorticoid receptor binding	-	0.6269	62.69%
Aromatase binding	-	0.8565	85.65%
PPAR gamma	-	0.8130	81.30%
Honey bee toxicity	-	0.8917	89.17%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.6477	64.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.77%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.06%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.40%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.21%	85.14%
CHEMBL4208	P20618	Proteasome component C5	85.93%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.52%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	83.64%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.43%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.19%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.50%	91.19%

Plants that contains it

• Calycophyllum spruceanum
• Cordiera macrophylla
• Dipsacus laciniatus
• Gentiana verna
• Neonauclea sessilifolia
• Scaevola floribunda
• Strychnos lucida

Cross-Links

• PubChem: 12769685
• LOTUS: LTS0183554
• wikiData: Q104201406