(1S,4aS,5R,6S,7R)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,6,7-tetrol

Details

• Internal ID: 696a3825-b5d9-44b9-b67e-e1badd36498c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,5R,6S,7R)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,6,7-tetrol
• SMILES (Canonical): CC1(C2C(OC=CC2(C(C1O)O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C[C@@]1([C@H]([C@H]([C@]2(C1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C15H24O11/c1-14(22)9-13(24-3-2-15(9,23)11(21)10(14)20)26-12-8(19)7(18)6(17)5(4-16)25-12/h2-3,5-13,16-23H,4H2,1H3/t5-,6-,7+,8-,9?,10+,11-,12+,13+,14-,15+/m1/s1
• InChI Key: DCMBJUSPXCDZSO-OSBKVORJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₁₁
• Molecular Weight: 380.34 g/mol
• Exact Mass: 380.13186158 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: -4.20
• Atomic LogP (AlogP): -4.49
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6493	64.93%
Caco-2	-	0.8819	88.19%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6124	61.24%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8611	86.11%
OATP1B3 inhibitior	+	0.9658	96.58%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9659	96.59%
P-glycoprotein inhibitior	-	0.8675	86.75%
P-glycoprotein substrate	-	0.9041	90.41%
CYP3A4 substrate	+	0.5848	58.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8472	84.72%
CYP3A4 inhibition	-	0.9429	94.29%
CYP2C9 inhibition	-	0.9393	93.93%
CYP2C19 inhibition	-	0.8656	86.56%
CYP2D6 inhibition	-	0.9368	93.68%
CYP1A2 inhibition	-	0.9079	90.79%
CYP2C8 inhibition	-	0.8237	82.37%
CYP inhibitory promiscuity	-	0.7839	78.39%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5951	59.51%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9806	98.06%
Skin irritation	-	0.8208	82.08%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4155	41.55%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8920	89.20%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6501	65.01%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	-	0.6428	64.28%
Androgen receptor binding	-	0.5119	51.19%
Thyroid receptor binding	+	0.5785	57.85%
Glucocorticoid receptor binding	-	0.5551	55.51%
Aromatase binding	+	0.6097	60.97%
PPAR gamma	+	0.6645	66.45%
Honey bee toxicity	-	0.8402	84.02%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.6235	62.35%

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	95.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.82%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.13%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.67%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	81.75%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	81.30%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.36%	89.00%
CHEMBL2581	P07339	Cathepsin D	80.19%	98.95%

Plants that contains it

• Cymbalaria muralis

Cross-Links

• PubChem: 102066446
• LOTUS: LTS0267410
• wikiData: Q104975589