6-Epiharpagide

Details

• Internal ID: 480943b9-6efd-476f-bc7c-b0eda0c6ac18
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,7-triol
• SMILES (Canonical): CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O
• SMILES (Isomeric): CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O
• InChI: InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3
• InChI Key: XUWSHXDEJOOIND-UHFFFAOYSA-N
• Popularity: 51 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₁₀
• Molecular Weight: 364.34 g/mol
• Exact Mass: 364.13694696 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -3.30
• Atomic LogP (AlogP): -3.46
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• 6-Epiharpagide
• 86362-16-5
• 6926-08-5
• CID 21604821
• CID 10044294
• (1R,4Ar,5S,7R)-7-methyl-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,7-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5539	55.39%
Caco-2	-	0.8786	87.86%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5003	50.03%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9738	97.38%
P-glycoprotein inhibitior	-	0.8870	88.70%
P-glycoprotein substrate	-	0.8768	87.68%
CYP3A4 substrate	+	0.6024	60.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8372	83.72%
CYP3A4 inhibition	-	0.9212	92.12%
CYP2C9 inhibition	-	0.9430	94.30%
CYP2C19 inhibition	-	0.8888	88.88%
CYP2D6 inhibition	-	0.9291	92.91%
CYP1A2 inhibition	-	0.9110	91.10%
CYP2C8 inhibition	-	0.7917	79.17%
CYP inhibitory promiscuity	-	0.8853	88.53%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5847	58.47%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9841	98.41%
Skin irritation	-	0.7876	78.76%
Skin corrosion	-	0.9491	94.91%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5277	52.77%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8427	84.27%
skin sensitisation	-	0.8931	89.31%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.5519	55.19%
Acute Oral Toxicity (c)	III	0.4625	46.25%
Estrogen receptor binding	-	0.6379	63.79%
Androgen receptor binding	-	0.5227	52.27%
Thyroid receptor binding	+	0.6031	60.31%
Glucocorticoid receptor binding	-	0.6043	60.43%
Aromatase binding	+	0.6340	63.40%
PPAR gamma	+	0.6450	64.50%
Honey bee toxicity	-	0.8498	84.98%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.5335	53.35%

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	96.32%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.95%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.26%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.49%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	90.26%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.19%	96.61%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.84%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.18%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.82%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.72%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.09%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.83%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.48%	91.24%

Plants that contains it

• Ajuga decumbens
• Ajuga pyramidalis
• Ajuga reptans
• Ajuga taiwanensis
• Ajuga turkestancia
• Angelonia integerrima
• Clerodendrum trichotomum
• Leonurus turkestanicus
• Physostegia virginiana
• Rogeria adenophylla
• Scrophularia ningpoensis
• Scrophularia nodosa
• Stachys officinalis
• Triaenophora rupestris
• Verbascum densiflorum
• Vitex agnus-castus

Cross-Links

• PubChem: 4678529
• LOTUS: LTS0155662
• wikiData: Q105342673