2-(Hydroxymethyl)-6-[[5-hydroxy-7-(phenylmethoxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]oxane-3,4,5-triol

Details

• Internal ID: c9b2ad0b-5c9c-4405-8b77-e33f51fb600a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-(hydroxymethyl)-6-[[5-hydroxy-7-(phenylmethoxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): C1=CC=C(C=C1)COCC2=CC(C3C2C(OC=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)COCC2=CC(C3C2C(OC=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• InChI: InChI=1S/C22H28O9/c23-9-16-18(25)19(26)20(27)22(30-16)31-21-17-13(8-15(24)14(17)6-7-29-21)11-28-10-12-4-2-1-3-5-12/h1-8,14-27H,9-11H2
• InChI Key: UWPGEJJSOSXSHN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₉
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.17333247 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.58
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5705	57.05%
Caco-2	-	0.8574	85.74%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5517	55.17%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8637	86.37%
OATP1B3 inhibitior	+	0.9608	96.08%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8024	80.24%
P-glycoprotein inhibitior	-	0.7206	72.06%
P-glycoprotein substrate	-	0.8042	80.42%
CYP3A4 substrate	+	0.5864	58.64%
CYP2C9 substrate	-	0.8103	81.03%
CYP2D6 substrate	-	0.8150	81.50%
CYP3A4 inhibition	-	0.9100	91.00%
CYP2C9 inhibition	-	0.8802	88.02%
CYP2C19 inhibition	-	0.7074	70.74%
CYP2D6 inhibition	-	0.8442	84.42%
CYP1A2 inhibition	-	0.8282	82.82%
CYP2C8 inhibition	+	0.5774	57.74%
CYP inhibitory promiscuity	-	0.6811	68.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6345	63.45%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9571	95.71%
Skin irritation	-	0.8114	81.14%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.5591	55.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.4301	43.01%
Micronuclear	-	0.6441	64.41%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8468	84.68%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5862	58.62%
Acute Oral Toxicity (c)	III	0.3988	39.88%
Estrogen receptor binding	+	0.6511	65.11%
Androgen receptor binding	+	0.5423	54.23%
Thyroid receptor binding	-	0.5460	54.60%
Glucocorticoid receptor binding	-	0.7271	72.71%
Aromatase binding	+	0.6734	67.34%
PPAR gamma	+	0.7054	70.54%
Honey bee toxicity	-	0.6968	69.68%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	-	0.3941	39.41%

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	93.73%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.29%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.34%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.09%	96.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.50%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.13%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	85.35%	94.73%
CHEMBL2581	P07339	Cathepsin D	83.77%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.65%	95.50%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	81.57%	95.48%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.47%	86.33%
CHEMBL3891	P07384	Calpain 1	80.32%	93.04%

Plants that contains it

• Melampyrum arvense

Cross-Links

• PubChem: 163010972
• LOTUS: LTS0169285
• wikiData: Q105280480