Nepetaside

Details

• Internal ID: 3f9ac395-9f8a-41e3-9182-a2aa45de3cef
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (4R,4aR,6R,7R,7aS)-4,7-dimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-1-one
• InChI: InChI=1S/C16H26O8/c1-6-5-22-15(21)11-7(2)9(3-8(6)11)23-16-14(20)13(19)12(18)10(4-17)24-16/h6-14,16-20H,3-5H2,1-2H3/t6-,7-,8+,9+,10+,11+,12+,13-,14+,16+/m0/s1
• InChI Key: CUIDBUWFCFYEPL-PIFFKTMJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₈
• Molecular Weight: 346.37 g/mol
• Exact Mass: 346.16276778 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.36
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• (-)-Nepetaside
• 114076-56-1
• CHEBI:143821
• AKOS040736282
• (4R,4aR,6R,7R,7aS)-4,7-dimethyl-1-oxooctahydrocyclopenta[c]pyran-6-yl beta-D-glucopyranoside
• (4R,4aR,6R,7R,7aS)-4,7-dimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6225	62.25%
Caco-2	-	0.8745	87.45%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6475	64.75%
OATP2B1 inhibitior	-	0.8531	85.31%
OATP1B1 inhibitior	+	0.8857	88.57%
OATP1B3 inhibitior	+	0.9452	94.52%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7876	78.76%
P-glycoprotein inhibitior	-	0.8735	87.35%
P-glycoprotein substrate	-	0.8379	83.79%
CYP3A4 substrate	+	0.5740	57.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8882	88.82%
CYP3A4 inhibition	-	0.8818	88.18%
CYP2C9 inhibition	-	0.9312	93.12%
CYP2C19 inhibition	-	0.8874	88.74%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.8769	87.69%
CYP2C8 inhibition	-	0.9127	91.27%
CYP inhibitory promiscuity	-	0.9011	90.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6989	69.89%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9590	95.90%
Skin irritation	-	0.8131	81.31%
Skin corrosion	-	0.9588	95.88%
Ames mutagenesis	-	0.6286	62.86%
Human Ether-a-go-go-Related Gene inhibition	-	0.6334	63.34%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9274	92.74%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5440	54.40%
Acute Oral Toxicity (c)	III	0.5274	52.74%
Estrogen receptor binding	+	0.6539	65.39%
Androgen receptor binding	-	0.5423	54.23%
Thyroid receptor binding	+	0.5222	52.22%
Glucocorticoid receptor binding	-	0.6016	60.16%
Aromatase binding	-	0.4896	48.96%
PPAR gamma	-	0.6229	62.29%
Honey bee toxicity	-	0.7379	73.79%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8085	80.85%

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	96.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.61%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	90.35%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.27%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.88%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.15%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.62%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.51%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.35%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.61%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	80.00%	92.50%

Plants that contains it

• Nepeta cataria

Cross-Links

• PubChem: 138453914
• LOTUS: LTS0189699
• wikiData: Q104970280