methyl (1S,4R,4aR,7R,7aS)-4'-[(1R)-1-hydroxyethyl]-5'-oxo-1-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,4,4a,7a-tetrahydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate

Details

• Internal ID: 7c30c6f0-30f6-4448-98e2-127feeba87ae
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4R,4aR,7R,7aS)-4'-[(1R)-1-hydroxyethyl]-5'-oxo-1-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,4,4a,7a-tetrahydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
• SMILES (Canonical): CC(C1=CC2(C=CC3C2C(OCC3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)OC1=O)O
• SMILES (Isomeric): C[C@H](C1=C[C@@]2(C=C[C@@H]3[C@@H]2[C@@H](OC[C@@H]3C(=O)OC)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC1=O)O
• InChI: InChI=1S/C21H28O12/c1-8(23)10-5-21(33-18(10)28)4-3-9-11(17(27)29-2)7-30-19(13(9)21)32-20-16(26)15(25)14(24)12(6-22)31-20/h3-5,8-9,11-16,19-20,22-26H,6-7H2,1-2H3/t8-,9+,11+,12-,13-,14-,15+,16+,19+,20-,21-/m1/s1
• InChI Key: GBCAZNAWDUIISE-NYEFWXDXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₁₂
• Molecular Weight: 472.40 g/mol
• Exact Mass: 472.15807632 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -2.65
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5216	52.16%
Caco-2	-	0.8518	85.18%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7394	73.94%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.8113	81.13%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8672	86.72%
P-glycoprotein inhibitior	-	0.7424	74.24%
P-glycoprotein substrate	-	0.5473	54.73%
CYP3A4 substrate	+	0.6705	67.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8928	89.28%
CYP3A4 inhibition	-	0.9115	91.15%
CYP2C9 inhibition	-	0.8852	88.52%
CYP2C19 inhibition	-	0.8745	87.45%
CYP2D6 inhibition	-	0.9344	93.44%
CYP1A2 inhibition	-	0.9194	91.94%
CYP2C8 inhibition	-	0.6952	69.52%
CYP inhibitory promiscuity	-	0.7734	77.34%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5664	56.64%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9481	94.81%
Skin irritation	-	0.7491	74.91%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5833	58.33%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.7957	79.57%
skin sensitisation	-	0.8428	84.28%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5877	58.77%
Acute Oral Toxicity (c)	III	0.5135	51.35%
Estrogen receptor binding	+	0.6955	69.55%
Androgen receptor binding	+	0.5501	55.01%
Thyroid receptor binding	-	0.5178	51.78%
Glucocorticoid receptor binding	+	0.6139	61.39%
Aromatase binding	+	0.6003	60.03%
PPAR gamma	+	0.5382	53.82%
Honey bee toxicity	-	0.6698	66.98%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.4077	40.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.23%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.97%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.86%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.11%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.72%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.70%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.31%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.07%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.07%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.96%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	83.60%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.66%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.60%	95.83%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.74%	91.24%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.65%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.29%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.35%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.10%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.08%	92.62%

Plants that contains it

• Allamanda schottii

Cross-Links

• PubChem: 162943489
• LOTUS: LTS0239551
• wikiData: Q105005759