Ixoside

Details

• Internal ID: e4fea83d-25bb-4bde-a474-1d4214a7a489
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4,7-dicarboxylic acid
• SMILES (Canonical): C1C=C(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)C(=O)O
• SMILES (Isomeric): C1C=C([C@@H]2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)C(=O)O
• InChI: InChI=1S/C16H20O11/c17-3-8-10(18)11(19)12(20)16(26-8)27-15-9-5(1-2-6(9)13(21)22)7(4-25-15)14(23)24/h2,4-5,8-12,15-20H,1,3H2,(H,21,22)(H,23,24)/t5-,8-,9+,10-,11+,12-,15+,16+/m1/s1
• InChI Key: AYRQUPRKTDTPEN-SQQPMCIGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₁₁
• Molecular Weight: 388.32 g/mol
• Exact Mass: 388.10056145 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.23
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• CHEMBL498244

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.9250	92.50%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6886	68.86%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.7553	75.53%
OATP1B3 inhibitior	+	0.9666	96.66%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9069	90.69%
P-glycoprotein inhibitior	-	0.8982	89.82%
P-glycoprotein substrate	-	0.9319	93.19%
CYP3A4 substrate	-	0.5110	51.10%
CYP2C9 substrate	-	0.6093	60.93%
CYP2D6 substrate	-	0.8811	88.11%
CYP3A4 inhibition	-	0.9096	90.96%
CYP2C9 inhibition	-	0.8881	88.81%
CYP2C19 inhibition	-	0.8765	87.65%
CYP2D6 inhibition	-	0.9195	91.95%
CYP1A2 inhibition	-	0.8957	89.57%
CYP2C8 inhibition	-	0.7912	79.12%
CYP inhibitory promiscuity	-	0.8290	82.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7174	71.74%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.8699	86.99%
Skin irritation	-	0.7804	78.04%
Skin corrosion	-	0.9527	95.27%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7183	71.83%
Micronuclear	-	0.5941	59.41%
Hepatotoxicity	-	0.8391	83.91%
skin sensitisation	-	0.8824	88.24%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6171	61.71%
Acute Oral Toxicity (c)	IV	0.3718	37.18%
Estrogen receptor binding	-	0.5283	52.83%
Androgen receptor binding	-	0.5060	50.60%
Thyroid receptor binding	-	0.6215	62.15%
Glucocorticoid receptor binding	-	0.6149	61.49%
Aromatase binding	-	0.5175	51.75%
PPAR gamma	-	0.5461	54.61%
Honey bee toxicity	-	0.8650	86.50%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7850	78.50%
Fish aquatic toxicity	+	0.6611	66.11%

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	95.22%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.15%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.96%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.97%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.28%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.03%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	81.01%	94.73%

Plants that contains it

• Alibertia edulis
• Antonia ovata
• Dolichandrone serrulata
• Leonotis nepetifolia
• Tecoma stans var. velutina

Cross-Links

• PubChem: 44583801
• LOTUS: LTS0050094
• wikiData: Q104399232