(5R,7S)-1,3,5-trimethoxy-7-methyl-3,4,4a,5,6,7a-hexahydro-1H-cyclopenta[c]pyran-7-ol

Details

• Internal ID: df567510-8a21-4bbf-afb0-cb5547636ecf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: (5R,7S)-1,3,5-trimethoxy-7-methyl-3,4,4a,5,6,7a-hexahydro-1H-cyclopenta[c]pyran-7-ol
• SMILES (Canonical): CC1(CC(C2C1C(OC(C2)OC)OC)OC)O
• SMILES (Isomeric): C[C@@]1(C[C@H](C2C1C(OC(C2)OC)OC)OC)O
• InChI: InChI=1S/C12H22O5/c1-12(13)6-8(14-2)7-5-9(15-3)17-11(16-4)10(7)12/h7-11,13H,5-6H2,1-4H3/t7?,8-,9?,10?,11?,12+/m1/s1
• InChI Key: AFKZZDROSIVIDQ-MUFLBICUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₂O₅
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.14672380 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• CHEBI:229174
• (5R,7S)-1,3,5-trimethoxy-7-methyl-3,4,4a,5,6,7a-hexahydro-1H-cyclopenta[c]pyran-7-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9461	94.61%
Caco-2	+	0.6860	68.60%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.5632	56.32%
OATP2B1 inhibitior	-	0.8502	85.02%
OATP1B1 inhibitior	+	0.9425	94.25%
OATP1B3 inhibitior	+	0.9094	90.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9650	96.50%
P-glycoprotein inhibitior	-	0.9153	91.53%
P-glycoprotein substrate	-	0.8679	86.79%
CYP3A4 substrate	+	0.5877	58.77%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.7933	79.33%
CYP3A4 inhibition	-	0.8895	88.95%
CYP2C9 inhibition	-	0.8794	87.94%
CYP2C19 inhibition	-	0.8774	87.74%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.7176	71.76%
CYP2C8 inhibition	-	0.8923	89.23%
CYP inhibitory promiscuity	-	0.9808	98.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8632	86.32%
Carcinogenicity (trinary)	Non-required	0.6669	66.69%
Eye corrosion	-	0.9762	97.62%
Eye irritation	-	0.7332	73.32%
Skin irritation	-	0.6428	64.28%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5227	52.27%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8482	84.82%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5857	58.57%
Acute Oral Toxicity (c)	III	0.4787	47.87%
Estrogen receptor binding	-	0.7727	77.27%
Androgen receptor binding	-	0.6878	68.78%
Thyroid receptor binding	+	0.5536	55.36%
Glucocorticoid receptor binding	-	0.8259	82.59%
Aromatase binding	-	0.6572	65.72%
PPAR gamma	-	0.6023	60.23%
Honey bee toxicity	-	0.6932	69.32%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.3808	38.08%

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	95.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.92%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.69%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.55%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.03%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	83.90%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.19%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.03%	97.28%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.82%	96.95%
CHEMBL259	P32245	Melanocortin receptor 4	82.73%	95.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.59%	85.14%

Plants that contains it

• Rehmannia glutinosa

Cross-Links

• PubChem: 5319847
• NPASS: NPC72993