Secologanin

Details

• Internal ID: c82ec1c2-1f71-4678-a0ad-483ed975ba11
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C(C1CC=O)C=C)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
• InChI Key: CSKKDSFETGLMSB-NRZPKYKESA-N
• Popularity: 102 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.13694696 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.78
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• 19351-63-4
• loniceroside
• (-)-Secologanin
• NK7B26K93T
• CHEBI:18002
• methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• METHYL (2S,3R,4S)-2-(BETA-D-GLUCOPYRANOSYLOXY)-4-(2-OXOETHYL)-3-VINYL-3,4-DIHYDRO-2H-PYRAN-5-CARBOXYLATE
• tert-butyl 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4,5-dihydro-1,2-oxazole-3-carbonyl]amino]butanoate
• NSC 640525
• NSC-640525
• Loniceroside (iridoid)
• UNII-NK7B26K93T
• SCHEMBL431171
• Secologanin, analytical standard
• CHEMBL1235867
• DTXSID30941033
• 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(.beta.-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, [2S-(2.alpha.,3.beta.,4.beta.)]-
• AKOS040753996
• LMPR0102070002
• NCGC00384550-01
• MS-26429
• HY-125598
• CS-0092439
• C01852
• J-012529
• Q1531155
• F19BE380-C97E-46CC-89C6-F6BCAFC793EC
• 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, (2S,3R,4S)-
• 3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester
• methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
• methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate
• NCGC00384550-01_C17H24O10_Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8144	81.44%
Caco-2	-	0.8648	86.48%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7386	73.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7564	75.64%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8711	87.11%
P-glycoprotein inhibitior	-	0.8234	82.34%
P-glycoprotein substrate	-	0.7622	76.22%
CYP3A4 substrate	+	0.6183	61.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8760	87.60%
CYP3A4 inhibition	-	0.8796	87.96%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.8714	87.14%
CYP2D6 inhibition	-	0.9292	92.92%
CYP1A2 inhibition	-	0.9349	93.49%
CYP2C8 inhibition	-	0.5826	58.26%
CYP inhibitory promiscuity	-	0.8829	88.29%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7391	73.91%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9426	94.26%
Skin irritation	-	0.8114	81.14%
Skin corrosion	-	0.9472	94.72%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5353	53.53%
Micronuclear	-	0.6441	64.41%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8702	87.02%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.7049	70.49%
Acute Oral Toxicity (c)	III	0.5435	54.35%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.4911	49.11%
Thyroid receptor binding	-	0.5548	55.48%
Glucocorticoid receptor binding	-	0.5242	52.42%
Aromatase binding	-	0.5356	53.56%
PPAR gamma	-	0.4857	48.57%
Honey bee toxicity	-	0.7776	77.76%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.3792	37.92%

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	95.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.44%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.74%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.18%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.09%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.16%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.69%	91.24%
CHEMBL4208	P20618	Proteasome component C5	85.67%	90.00%
CHEMBL5028	O14672	ADAM10	83.16%	97.50%
CHEMBL2581	P07339	Cathepsin D	82.40%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.17%	86.33%

Plants that contains it

• Acacia aulacocarpa
• Acicarpha tribuloides
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Catharanthus roseus
• Cinchona calisaya
• Cruckshanksia pumila
• Cruckshanksia verticillata
• Cryptocarya aschersoniana
• Curtia tenuifolia
• Desfontainia spinosa
• Dipsacus inermis
• Eupatorium argentinum
• Garcinia madruno
• Gentiana verna
• Guatteria ucayalina
• Guettarda speciosa
• Hydrangea macrophylla
• Juniperus brevifolia
• Lippia origanoides
• Lonicera caerulea
• Lonicera japonica
• Lonicera morrowii
• Lonicera periclymenum
• Lonicera tatarica
• Peritassa compta
• Psiadia dentata
• Scutellaria lateriflora
• Strychnos nux-vomica
• Strychnos spinosa

Cross-Links

• PubChem: 161276
• NPASS: NPC312137
• LOTUS: LTS0199033
• wikiData: Q1531155