Secologanoside

Details

• Internal ID: 65f79c9a-0d92-4ad7-b272-e3c2ef801bd1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S)-4-(carboxymethyl)-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
• SMILES (Canonical): C=CC1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)CC(=O)O
• SMILES (Isomeric): C=C[C@@H]1[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)O)CC(=O)O
• InChI: InChI=1S/C16H22O11/c1-2-6-7(3-10(18)19)8(14(23)24)5-25-15(6)27-16-13(22)12(21)11(20)9(4-17)26-16/h2,5-7,9,11-13,15-17,20-22H,1,3-4H2,(H,18,19)(H,23,24)/t6-,7+,9-,11-,12+,13-,15+,16+/m1/s1
• InChI Key: RGTONEMDTVVDMY-GRTPNEQMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34 g/mol
• Exact Mass: 390.11621151 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.98
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 59472-23-0
• HY-N6876
• AKOS040760115
• AC-34172
• MS-26494
• CS-0100464
• (2S,3R,4S)-4-(carboxymethyl)-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8117	81.17%
Caco-2	-	0.9009	90.09%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6826	68.26%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.7591	75.91%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9689	96.89%
P-glycoprotein inhibitior	-	0.8610	86.10%
P-glycoprotein substrate	-	0.9252	92.52%
CYP3A4 substrate	+	0.5081	50.81%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.8774	87.74%
CYP3A4 inhibition	-	0.8274	82.74%
CYP2C9 inhibition	-	0.8996	89.96%
CYP2C19 inhibition	-	0.8965	89.65%
CYP2D6 inhibition	-	0.9214	92.14%
CYP1A2 inhibition	-	0.9463	94.63%
CYP2C8 inhibition	-	0.7411	74.11%
CYP inhibitory promiscuity	-	0.9394	93.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7785	77.85%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.8492	84.92%
Skin irritation	-	0.8065	80.65%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	-	0.5893	58.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.6253	62.53%
Micronuclear	-	0.6482	64.82%
Hepatotoxicity	-	0.7430	74.30%
skin sensitisation	-	0.8460	84.60%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6282	62.82%
Acute Oral Toxicity (c)	III	0.4892	48.92%
Estrogen receptor binding	+	0.5327	53.27%
Androgen receptor binding	-	0.5518	55.18%
Thyroid receptor binding	+	0.5230	52.30%
Glucocorticoid receptor binding	+	0.5522	55.22%
Aromatase binding	+	0.6007	60.07%
PPAR gamma	-	0.5623	56.23%
Honey bee toxicity	-	0.7891	78.91%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8400	84.00%
Fish aquatic toxicity	+	0.6770	67.70%

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	91.95%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.37%	91.11%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.69%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.23%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.71%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.94%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.87%	86.92%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.64%	93.00%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.80%	95.71%
CHEMBL3401	O75469	Pregnane X receptor	82.30%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.41%	86.33%
CHEMBL1881	P43116	Prostanoid EP2 receptor	80.69%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.52%	89.00%

Plants that contains it

• Fagraea racemosa
• Fontanesia fortunei
• Gentianella nitida
• Ligustrum vulgare
• Lonicera confusa
• Lonicera hypoglauca
• Lonicera japonica
• Lonicera macrantha
• Lonicera periclymenum
• Olea europaea
• Phillyrea latifolia
• Poraqueiba guianensis
• Sphenoclea zeylanica
• Strychnos spinosa
• Syringa vulgaris
• Tripterospermum japonicum

Cross-Links

• PubChem: 14136854
• NPASS: NPC217853
• LOTUS: LTS0242890
• wikiData: Q104392505