8-O-Acetylharpagide

Details

• Internal ID: e865223b-73fe-46a8-9e5b-fa35d994d31b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-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-7-yl] acetate
• SMILES (Canonical): CC(=O)OC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)C
• SMILES (Isomeric): CC(=O)O[C@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)C
• InChI: InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1
• InChI Key: CAFTUQNGDROXEZ-XBDCZORHSA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₁₁
• Molecular Weight: 406.40 g/mol
• Exact Mass: 406.14751164 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -2.89
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 6926-14-3
• 8-Acetylharpagide
• Acetylharpagide
• 8-?O-?Acetylharpagide
• CHEMBL523290
• 3-Acetylharpagide
• 8-OAc-harpagide
• 8--cetylharpagide
• MLS002473158
• MEGxp0_000602
• ACon1_000486
• DTXSID101346466
• HMS2198M04
• HY-N0757
• BDBM50250347
• MFCD03700750
• s9474
• AKOS030530356
• NCGC00169032-01
• NCGC00169032-03
• AC-34969
• BS-17945
• SMR001397250
• 8-Acetylharpagide, >=85% (LC/MS-ELSD)
• CS-0009785
• NCGC00169032-03_C17H26O11_(1S,4aS,5R,7S,7aS)-1-(beta-D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5457	54.57%
Caco-2	-	0.8603	86.03%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6137	61.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8796	87.96%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9042	90.42%
P-glycoprotein inhibitior	-	0.8550	85.50%
P-glycoprotein substrate	-	0.8171	81.71%
CYP3A4 substrate	+	0.6448	64.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	-	0.8706	87.06%
CYP2C9 inhibition	-	0.9455	94.55%
CYP2C19 inhibition	-	0.9393	93.93%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	-	0.9070	90.70%
CYP2C8 inhibition	-	0.7100	71.00%
CYP inhibitory promiscuity	-	0.9031	90.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6309	63.09%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9764	97.64%
Skin irritation	-	0.7310	73.10%
Skin corrosion	-	0.9421	94.21%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5423	54.23%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.8047	80.47%
skin sensitisation	-	0.8800	88.00%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4885	48.85%
Acute Oral Toxicity (c)	III	0.5000	50.00%
Estrogen receptor binding	+	0.5382	53.82%
Androgen receptor binding	+	0.5444	54.44%
Thyroid receptor binding	+	0.5866	58.66%
Glucocorticoid receptor binding	-	0.5326	53.26%
Aromatase binding	+	0.6401	64.01%
PPAR gamma	+	0.5626	56.26%
Honey bee toxicity	-	0.8329	83.29%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7555	75.55%
Fish aquatic toxicity	-	0.3698	36.98%

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	98.00%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.62%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.86%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.89%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.88%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.34%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.80%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.01%	91.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.87%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.61%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	81.41%	90.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.40%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.61%	86.33%

Plants that contains it

• Ajuga decumbens
• Ajuga integrifolia
• Ajuga pyramidalis
• Ajuga reptans
• Ajuga taiwanensis
• Leonurus persicus
• Leonurus turkestanicus
• Otostegia fruticosa
• Phyllanthus emblica
• Physostegia virginiana
• Plagiomnium cuspidatum
• Scrophularia deserti
• Stachys officinalis
• Stachys recta
• Vitex agnus-castus

Cross-Links

• PubChem: 9978650
• NPASS: NPC294643
• ChEMBL: CHEMBL523290
• LOTUS: LTS0114338
• wikiData: Q104391699